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Is there any better place to spend your summer vacation than on the white sand beaches of Siesta Key, frolicking in the surf, building sandcastles at shore’s edge, and just living the beach life you have dreamed about your entire life? Of course there isn’t and as your summer getaway to our Rent Siesta Key escapes draws even closer, we thought we would take a few minutes to offer up some ideas of all the other things you can do to fill your vacation hours. You’ve already figured out the beach thing and you could spend every day all day playing on our sandy shores, but you’ve come all this way and it would be a shame to miss out on all of these wonderful adventures.

Siesta Key  Bike and Kayak, 1224 Old Stickney Point Road, Open 9-5 Daily

Sometimes it is the simpler pleasures that make the largest impact and a ride around Siesta Key aboard a colorful beach cruiser could be just the thing to make your fantastic Florida getaway even sweeter. Siesta Key Bike and Kayak rents a variety of bikes, e-bikes, and scooters ensuring that you can find the piece of equipment that makes your vacation shine brighter. They also rent beach gear, allowing guests to have a great time on the beach without having to lug chairs and umbrellas around, but many of our Rent Siesta Key vacation rentals will also offer much of the same equipment, helping to save you a little cash during your vacation.

Parasail Siesta, 1250 Stickney Point Road, open 8-6:30 Daily

We all have dreams in which we are flying and under normal circumstances the only way we can fly for real is while seated in a metal tube with a seatbelt wrapped around our waists. Parasailing, however, allows us to enjoy a similar sensation, flying through the air dangling from a parachute as the wonderful people from Parasail Siesta guide the boat that provides the power that helps you fly. Using the latest equipment and following all the safety guidelines, the rates are reasonably priced, $79 per person, and the experience will bring you memories you will never forget.

Shopping Expeditions

On a summer day that feels a little too warm to be outside, shopping for treasures and souvenirs is an activity that most travelers enjoy and the shops of Siesta Key provide a variety of wares that will bring back wonderful memories of that time you spent your vacation one of Florida’s most beautiful Keys. Gidget’s Coastal Provisions, 5242 Ocean Boulevard, is one of our favorite shops, filled with beach themed items that will look amazing on the shelves at your own home. Looking for a cute new dress to wear out to your dinner with the hubs? Casa del Sol Boutique, 5212 Ocean Boulevard, offers men’s and women’s clothing, accessories, and even some houseware and gift items. And because there is no greater pleasure than attending a Farmers Market on a gorgeous summer day, your Sunday morning on Siesta Key can be spent wandering the aisles of the Siesta Key Farmers Market, 5211 Ocean Boulevard. They are open from 9AM until 2PM.

Sarasota Classic Car Museum, 5500 N Tamiami Trail, Open Daily from 9-6

Another fascinating indoor activity perfect for rainy days or for those days you just don’t want to brave the heat, is a visit to the Sarasota Classic Car Museum. Offering 60,000 square feet and a revolving collection of colorful classic cars, their latest exhibit, The Art of Ferdinand Porsche and Enzo Ferrari, is a fascinating deep dive into the history of two of the greatest car designers in the world. This museum may be changing to a new location soon, we just don’t know when and where but it will be announced as soon as that information is available.

Play at Home With Rent Siesta Key

Some of your finer moments of fun and relaxation will take place within the boundaries of your Rent Siesta Key home sweet vacation home or condo. Every property on Siesta Key is located within walking distance of the white sand beaches and many will be located within sight of those turquoise waters. Spend a few hours hanging out by the pools that are a part of most escapes, eschewing salt and sand for comfy loungers and crystal blue chlorinated waters or simply relax on patios that overlook the Gulf of Mexico, feeling salty breezes kiss your cheeks as the sea waters crash against those impossibly white shores.  Movie nights are adventures in comfort as you watch from the depths of plush sofas as the large screen pictures make you feel as if you are an extra in the movie and at night, when the moon lights up the waves with its cool glow, you may miss most of THAT show as you are sleeping soundly in soft as cloud beds. Contact us and reserve your favorite Siesta Key sanctuary today. 

Get ready to discover the ultimate spring getaway on Siesta Key, where sun-kissed beaches and vibrant energy await eager vacationers. Prepare to dive into crystal-clear waters, lounge on powdery white sands, and explore the charm of this coastal gem. With this comprehensive guide, you can embark on a journey of unforgettable Siesta Key spring experiences and create lasting memories on Florida’s stunning Gulf Coast.

Check Out Our Spring Rentals in Siesta Key

Utilize This Comprehensive Guide to Spending Spring in Siesta Key

As the temperatures rise and the days grow longer, Siesta Key comes alive with an array of activities and experiences perfect for a spring getaway. Whether you’re seeking relaxation on the beach, thrilling water adventures, or cultural exploration, Siesta Key has something for everyone to enjoy during the spring season.

Siesta Key is renowned for its stunning beaches, and spring is the perfect time to soak up the sun and sink your toes into the powdery white sands. You can spend your days lounging on Siesta Beach, consistently ranked among the top beaches in the world for its pristine shores and turquoise waters. For a quieter escape, venture to Crescent Beach or Turtle Beach, where you can unwind in a tranquil setting away from the crowds.

In addition to its beaches, Siesta Key offers a host of outdoor water activities to enjoy during spring. Embark on a kayaking or paddleboarding adventure through the mangrove tunnels of South Lido Key Nature Park, where you can spot native wildlife and explore secluded waterways. For those seeking a bit more excitement, you can hop aboard a parasailing excursion and soar above the Gulf of Mexico for panoramic views.

 

You can also experience the magic of Siesta Key, with a sunset cruise along its stunning coastline. As the golden hour approaches, embark on a journey that promises breathtaking views and unforgettable moments. Get ready to glide across tranquil waters, surrounded by the warm hues of the setting sun painting the sky. Feel the gentle sea breeze caress your skin as you relax on deck, soaking in the moment.

Another enchanting water excursion worth trying during your spring getaway to Siesta Key, FL, is a dolphin-watching tour. Get ready to cruise along the crystal-clear waters of the Gulf of Mexico, where playful dolphins frolic and dance in their natural habitat. Feel the excitement build as you spot these majestic creatures leaping gracefully through the waves.
For the marine life lovers, get ready to indulge in the vibrant underwater world of Siesta Key, FL, during your spring getaway with snorkeling and scuba diving adventures. Prepare to explore the pristine waters of the Gulf of Mexico, where colorful coral reefs and an abundance of marine life await.

Snorkeling allows you to glide effortlessly along the surface, observing tropical fish darting among the coral gardens and graceful sea turtles gliding by. For those seeking a more immersive experience, scuba diving offers the opportunity to delve deeper into the depths, where hidden treasures and mysterious shipwrecks await discovery.

You can also embark on an angler’s adventure during your spring escape to Siesta Key, FL, with a thrilling fishing charter experience. Situated along the stunning Gulf Coast, Siesta Key offers some of the best fishing opportunities in the region. Joining a fishing charter allows you to explore the bountiful waters of the Gulf of Mexico under the guidance of experienced local captains.

Beyond the Turquoise Waters

For those looking to explore beyond the Gulf and beaches, Siesta Key offers a variety of tours and excursions to showcase the area’s natural beauty and rich history. You can embark on a guided eco-tour of nearby Sarasota Bay, where you can learn about the diverse ecosystems that thrive in the region and spot dolphins playing in the waves.

For the ornithologists and ornithophiles, you can escape into the wild beauty of Siesta Key, FL, with a nature walk or birdwatching tour at Myakka River State Park. As spring breathes new life into the landscape, this sprawling park becomes a haven for nature enthusiasts seeking adventure and tranquility.

History buffs will enjoy a visit to the Historic Spanish Point, a sprawling outdoor museum featuring archaeological exhibits, historic buildings, and lush gardens. For the nature lovers, you can visit the Marie Selby Botanical Gardens in nearby Sarasota to see exotic plants and orchids.

 

Apart from enjoying these laidback cultural experiences and outdoor adventures, you can embark on a scenic bike ride through the breathtaking landscapes of Siesta Key, FL. With its flat terrain and abundance of bike-friendly paths including Legacy Trail, Siesta Key is the perfect destination for cyclists of all ages and skill levels.

You can also take an escape to the lush greens and pristine fairways of Siesta Key, FL, for an unforgettable golfing experience during your spring getaway. With its year-round sunny weather and scenic courses, Siesta Key is a golfer’s paradise waiting to be explored. Get ready to tee off against the backdrop of swaying palm trees and scenic views of the Gulf Coast, as you challenge yourself on championship-level courses.

Bank on Your Shoppaholic Spirit

In addition to providing vacationers with a host of historical structures and scenic landscapes, Siesta Key features a vibrant downtown ideal for shopping. Indulge in a shopping spree like no other during your spring getaway to Siesta Key, FL. The downtown part of this charming destination offers a plethora of unique boutiques, galleries, and shops just waiting to be explored.

Get ready to stroll along the vibrant streets of Siesta Key Village, where you’ll discover an eclectic array of stores offering everything from trendy beachwear and artisanal crafts to one-of-a-kind souvenirs and gifts. Be ready to browse through quaint shops filled with local artwork, handmade jewelry, and stylish apparel, each offering its own distinct charm and character.

Additionally, you can take your time to wander through the bustling markets and squares, soaking in the lively atmosphere and vibrant energy of this coastal community. Whether you’re searching for the perfect memento to commemorate your trip or simply looking to indulge in some retail therapy, shopping in Siesta Key promises a delightful experience for all.

Experience Comfort and Spring Events the Florida Way

Springtime in Siesta Key also brings a calendar full of exciting events and festivals for visitors to enjoy. One highlight is the Siesta Key Craft Festival, held annually in April, where you can browse a variety of handmade goods from local artisans while enjoying live music and delicious food. Another must-see event is the Siesta Fiesta, a lively arts and crafts festival featuring works by talented artists from across the country.

Upon enjoying these activities, get ready to indulge in ultimate relaxation and rejuvenation with a luxurious spa day experience. Treat yourself to a pampering session at one of the area’s renowned spas, where expert therapists and tranquil surroundings await to melt away your stresses and leave you feeling refreshed and revitalized.

Take Your Palate on A Culinary Excursion

No trip to Siesta Key would be complete without experiencing its vibrant dining scene, which boasts an array of restaurants and eateries offering fresh seafood and international cuisine. Get ready to indulge in fresh Gulf shrimp at a waterfront seafood shack, savor authentic Italian dishes at a cozy trattoria, or treat yourself to tropical cocktails and sunset views at a beachside tiki bar.

Additionally, you can savor the taste of the sea with succulent shrimp, flaky grouper, and buttery lobster, sourced fresh from the surrounding waters. Indulge in tropical fruits and flavors with refreshing cocktails and mocktails crafted from exotic ingredients like coconut, mango, and pineapple. Whether you’re dining al fresco or cozying up in a charming beachside bistro, the culinary scene in Siesta Key promises to delight.

End Your Days in a Vibrant Manner

As the sun sets on another perfect day in Siesta Key, the nightlife comes alive with live music, dancing, and entertainment options for every taste. You can opt to head to Siesta Village to mingle with locals and travelers at bars and nightclubs, or enjoy a romantic sunset stroll along the beach with your loved one. Whether you’re seeking a night of revelry or a quiet evening, Siesta Key offers endless opportunities to make memories.

Siesta Key is the ultimate destination for a spring getaway, offering pristine beaches, exciting activities, delicious dining, and unforgettable experiences for everyone. Whether you’re seeking relaxation, adventure, or cultural exploration, Siesta Key has something to offer everyone during spring. So, pack your bags, grab your sunglasses, and get ready to make memories that will last a lifetime in this Florida paradise.

A Home Base for Your Siesta Key Spring Adventures

Planning your spring getaway to Siesta Key, FL? Look no further for your ideal vacation rental. Nestled in the heart of this breathtaking paradise, our rentals offer an array of features and amenities to ensure your stay is nothing short of extraordinary. From stunning beachfront views to luxurious accommodations, we have everything you need for a memorable escape.

As you step into your vacation oasis, get ready to be greeted by spacious and beautifully appointed interiors. Our rentals boast modern furnishings, plush bedding, and all the comforts of home, providing the perfect retreat after a day of exploration. Whether you’re traveling solo, with a loved one, or the whole family, we have accommodations to suit your every need and preference.

Besides enjoying comfort, prepare to wake up to the sound of gentle waves and bask in the Florida sunshine from your balcony or terrace. Our rentals offer unparalleled access to the pristine beaches of Siesta Key, allowing you to enjoy endless days of sun, sand, and surf right at your doorstep. You can also spend your mornings lounging on the shore, building sandcastles with the kids, or strolling along the water’s edge.

After a day of seaside adventures, return to your rental and unwind in style. You can take a refreshing dip in the sparkling pool, surrounded by lush tropical landscaping and swaying palm trees. Or perhaps you prefer to relax in the soothing waters of the hot tub, letting your cares melt away as you gaze up at the starry night sky. Whatever your preference, our amenities are designed to enhance your vacation experience.

 

Hungry for a taste of local flavor? Our rentals are conveniently located near an array of dining options, ranging from casual beachside cafes to upscale waterfront restaurants. Get ready to indulge in fresh seafood, savor mouthwatering cocktails, and indulge in the vibrant culinary scene of Siesta Key. With so many delicious choices just moments away, you’ll never have to venture far for a satisfying meal.

Looking to explore the natural beauty and attractions of Siesta Key? Our rentals provide easy access to a wealth of outdoor activities and sightseeing opportunities. From kayaking and paddleboarding to dolphin-watching tours and sunset cruises, there’s no shortage of ways to experience the magic of this enchanting destination. You can let us help you plan the perfect itinerary for your spring getaway.

At the end of the day, be ready to retreat to the comfort and tranquility of your vacation rental, where relaxation and rejuvenation await. You can curl up with a good book, catch up on your favorite shows, or simply enjoy the company of loved ones as you reminisce about the day’s adventures. With our impeccable service and attention to detail, your spring getaway to Siesta Key is sure to be one for the books.

Don’t wait any longer to book your dream vacation rental in Siesta Key, FL. You can consider our services today to reserve your slice of paradise and start counting down the days until your unforgettable spring escape. We can’t wait to welcome you to our little slice of heaven on the Gulf Coast.

Book Vacation Rentals in Siesta Key

Book Your Spring Stay in One of Our Breathtaking Siesta Key Vacation Rentals

As you plan your spring getaway to Siesta Key, remember to embrace every moment of sun, sand, and adventure this vibrant destination has to offer. From beachfront bliss to exciting outdoor excursions, there’s something for everyone to enjoy. You can contact us today to book your stay and make memories that will last a lifetime!

After a long winter of snow, ice, and gray skies we are pretty sure you are ready for the unofficial kickoff to summer fun to begin and what better place to enjoy the long weekend than in the area where summer is eternal? Siesta Key is known for its white sand beaches, its Sunday Drum Circles and for being home to our finest Rent Siesta Key summer sanctuaries and this guide to all you can expect from Memorial Day Weekend will ensure you are even more anxious to get the celebration started. Tune out the gray skies in your hometown and tune in to the adventures that are waiting to be explored in the Sunshine State; your memorial day getaway in Siesta Key, Florida will be here before you know it!

It’s Beach Time

Of course one of the first things you are going to want to do is bury your toes in the sand, so grab your gear, including plenty of sunscreen if you want to enjoy the entire weekend pain free, and head to the beaches of Siesta Key. What you do on your beach days is all up to you, but we will tell you the water will be perfect, the sun will be shining, and if rain does drift in, wait a few minutes and it will drift right back out again! The sands on our beaches are whiter than what you may expect, created from pure Appalachian quartz that has eroded over the centuries and found its way to Siesta Key.

A Florida Tradition

If you have spent any time at all in Florida, you may have recognized we move a little slower, we relax a little harder, and dressing up means we put our sparkly flip flops on instead of our well worn rubber ones. We appreciate a cold beer on a hot day, we worship fresh caught grouper sandwiches, and it is a tradition to enjoy both at restaurants and bars that look out over the waters, including Turtle’s Restaurant, located at 8875 Midnight Pass Road. Open every day from 11:30 until 9, patrons can sit out at patio tables overlooking the water, sipping beer (or rum runners, another popular Florida drink) savoring grouper sandwiches, and if lucky, catching glimpses of dolphins, manatees, and even some very friendly green parrots as they do. 

Shopping the Sales

We love a good sale and although traditionally the sales around Memorial Day tend to be for mattresses or appliances, the shops on Siesta Key are destined to have some deals going on that you won’t be able to resist. Beach Bazaar, 5211 Ocean Boulevard offers everything you need for the beach, while also providing a healthy souvenir selection that travelers adore. Foxy Lady, 209 Beach Road, is a ladies’ clothing boutique filled with fun and stylish apparel and on a rainy day? Crossings at Siesta Key, 3501 S Tamiami Trail, is a mall that deserves to be explored in depth.

The Beach Club, 5151 Ocean Boulevard

The nightlife in Sarasota, while not as frenetic as our neighbors to the south of us (Miami) is quite thriving and a night out on the town will fulfill all your hopes if you start and end it at the Beach Club. Offering live music seven nights a week, DJs, themed night, and special events, the music plays until the wee hours of the morning, the dance floor is always hopping, and the views of the sea will ensure that even as you dance the night away, you will still be able to soak in the serenity of the waters that surround Siesta Key, Remember, the pace is slower here and even as you dance, drink, and celebrate the extra day off, stepping back to appreciate the sounds of waves lapping against the deck, the way the stars sparkle brightly in the night sky, or the soft feel of salt air kissing your cheeks will give you the energy to keep the party going on a little longer.

Family Moments That Matter

There will be a lot going on during your Memorial Day Weekend on Siesta Key, but as you enjoy beach moments, shopping sprees, delicious foods, and nights out on the town, it is your traveling companions that will bring you the greatest joy and spending time with them at home in your Rent Siesta Key sanctuary will bring you the moments that matter most. Grilling by the pool, laughing at the antics of giggly tweens splashing and playing in the clear blue waters, playing the music you have loved your whole life—these are what makes Memorial Day memorable, and although you could enjoy them anywhere on Siesta Key, somehow they will be more special because you spent those moments with Rent Siesta Key! Contact us and reserve your favorite escape today.

There once was a time when planning a vacation involved packing the station wagon with sandwiches and pillows for the kids, driving long distances while only stopping for gas, and staying in roadside hotels every night of the drive. Once we arrived at our destination, another hotel, albeit a slightly nicer one, would be our home for the duration of our stay, and the bickering and irritations would commence as families, no matter how big, would cram themselves into one room, sharing beds, floor space, and the single bathroom. Today, times are much more civilized, as we fly more, argue less, and choose comfortable and luxurious vacation condo rentals for our accommodations, but if you are still considering a hotel for your Siesta Key vacation, our Rent Siesta Key guide to all the reasons our rentals are better than hotel rooms will help you see the error in your ways.

The Money You Will Save

Will a Rent Siesta Key condo cost more than a hotel room? The rental fees may or may not be slightly more than a hotel room, but when you realize that just as your parents saved money by packing sandwiches in the cooler and avoiding fast food on those long ago road trips of your youth, you too will be able to save money when you choose a condo over a hotel by utilizing the fully equipped kitchens in the space. Scramble eggs for breakfast most days, make your own sandwiches to place in a cooler to enjoy during your days on the beach, and at dinner, well, there are a LOT of wonderful restaurants to choose from, but no one will judge you for choosing to eat in a couple of nights of your stay. Of course, even as the savings add up, you will want to experience a taste of Siesta Key at least a few times, savoring the fresh seafood that we promise tastes better than any other place on earth!

The Space Your Family Needs

Up until now we have been concentrating on the benefits of condos versus hotel rooms, but we do need to point out that Rent Siesta Key also offers homes with as many as 5 bedrooms, ensuring that even the largest families have the space they need to feel comfortable and relaxed. Homes or condos with rooms for the kids and parents give every traveler a place to retreat when the bickering becomes too intense. We aren’t going to pretend that choosing Rent Siesta Key will stop all arguments; we offer magic in our properties, but we can’t promise the moon. We can, however, ensure that the twins have their own space, that parents can watch the shows they want to watch on a rainy night without having to argue with the kiddos, and we think that is a good compromise.

Do You Really Want to Hear Your Neighbor’s Arguments?

No matter how nice the hotel, the walls between the rooms always seem to be paper thin, ensuring that you can hear the television shows they are watching, that you can’t avoid learning the intimate details of the relationship between your neighbors, and that you jump every time they slam the door. (And if they are traveling with kids, you know how many times that will be!) Even our condos, that yes, provide neighbors beside, above, and sometimes below, offer a barrier between the properties, walls that ward off the sounds of arguments, televisions, and although you may still hear a few slamming doors, (kids will be kids) those doors won’t be slammed in the middle of the night, ensuring that your sleep will be uninterrupted and as restful as you need.

The Style You Deserve

If you have been in one hotel, you have been in them all, at least as far as décor and style is concerned. The furnishings, although colorful and sturdy, are generally bought at hospitality warehouses, designed to withstand the crowds. Our condos and homes, however, offer that sense of style that please all the senses, with artwork often created by local artists, linens that feel soft against skin that may be slightly sunburned, and sofas that envelope guests in comfort, inviting you to sink into their depths and stay longer than you imagined you would. Add in modern conveniences that can include professional quality appliances, state of the art televisions, and of course, high-speed internet that you don’t have to pay extra to enjoy. All of these things may not sound like much one by one, but when you add it up, the answer is clear. Choosing a Rent Siesta Key condo is far better than choosing a hotel. Contact us and reserve your favorite today!

Craving an unforgettable culinary adventure in Siesta Key? Look no further than these hidden waterfront gems, where exquisite plates dance with breathtaking settings and unforgettable service. Imagine sunsets that melt into the Gulf, waves serenading your meal, and delectable dishes that tantalize your taste buds. That said, buckle up, foodies, for a delicious dive into the heart of Siesta Keys’ oceanview dining scene.

High-End Restaurants for Siesta Keys Oceanview Dining

First, prepare to be swept away by Ophelia’s on the Bay. Imagine floor-to-ceiling windows showcasing the Gulf’s shimmering embrace, while you savor lobster thermidor bathed in moonlight. Get ready to also savor the indulgence of their tasting menu, a symphony of seasonal surprises that will tantalize your taste buds. You can also opt for the sunset cruise, where dolphins and delectable dishes offer unforgettable memories.

Next, you can embark on a journey to The Cottage, where vibrant tropical vibes meet culinary artistry. Imagine vibrant bursts of mango salsa atop pan-seared scallops, or the melt-in-your-mouth decadence of their signature miso-glazed Chilean sea bass. Don’t miss their “Island Nights” every Tuesday, where live music serenades you under a canopy of stars, making every bite a celebration of island life.

To all seafood lovers, Siesta Key Oyster Bar‘s laid-back charm and Gulf-to-table freshness are calling your name. Get ready to dive into their signature “cracked conch” appetizer, a delightful mix of textures and flavors. Feeling fancy? The lobster mac and cheese, infused with truffle oil, is pure decadence. You can wash it all down with a glass of their crisp Sauvignon Blanc, and soak in the breathtaking sunset views.

Time for a touch of elegance? Chart House Restaurant on Longboat Key offers panoramic vistas and an ambiance that oozes sophistication. Their signature Chilean sea bass, with a macadamia nut crust and a touch of citrus beurre blanc, is a must-try. Additionally, their bone-in ribeye, cooked to perfection, is a carnivore’s dream. You can also indulge in their decadent chocolate lava cake, offering a warm, gooey finale.

Another waterfront restaurant worth trying out is the Turtle Beach Grill. Here, you can savor their famous “Floribbean” cuisine, a fusion of fresh seafood and tropical flavors. The blackened mahi-mahi tacos, with their vibrant pico de gallo and creamy avocado crema, are a taste of paradise. Feeling adventurous? The pan-seared scallops, drizzled with a mango salsa, are a burst of sweet and savory perfection.

Craving a taste of Italy with a splash of coastal charm? Cafe Gabbiano awaits. Picture yourself twirling al dente pasta bathed in rich marinara, all while the Gulf whispers secrets on the ocean breeze. Treat yourself to their “Sunset Aperitivo” ritual, where delectable cicchetti and crafted cocktails paint the perfect prelude to a balmy evening.

For the steak-lover with a refined palate, Siesta Key Summer House is your haven. Imagine the sizzle of perfectly cooked Wagyu beef, the delicate dance of chimichurri on succulent lamb chops. You can indulge in their “Dry-Aged Steak Night” for a carnivore’s paradise, where perfectly aged cuts meet innovative sides and an award-winning wine list.

Finally, prepare to be dazzled by The Grove, where rustic elegance meets modern culinary mastery. Imagine the explosion of flavors in their pan-roasted duck à l’orange, or the melt-in-your-mouth decadence of their chocolate lava cake. Don’t miss their “Thursday Night Jazz,” where sultry tunes intertwine with delectable dishes, creating a truly immersive experience.

Mid-Range

Craving a delicious meal that won’t break the bank? Siesta Key offers a treasure trove of mid-range restaurants that tantalize your taste buds without hurting your wallet.

For starters, you can embrace the Key West vibes at Daiquiri Deck Siesta Key Village. Sip on their famous frozen daiquiris in flavors like mango, piña colada, or strawberry, and savor their delicious seafood dishes like coconut shrimp or blackened mahi-mahi tacos. Live music and a vibrant atmosphere make it ideal for a fun night out with friends.

Alternatively, you can indulge in succulent steaks and seafood at Viento Kitchen & Bar. This stylish eatery boasts a vibrant ambiance and a menu that highlights fresh, sustainable ingredients. Don’t miss their mouthwatering grouper with roasted vegetables or their perfectly cooked filet mignon.

 

For a lively atmosphere with a marina backdrop visit The Boatyard Waterfront Bar and Grill. This lively spot offers a true taste of Old Florida charm. Get ready to dock your boat, grab a seat on their expansive patio, and indulge in their fresh seafood platters, juicy burgers, or baskets of crispy fried shrimp. Don’t forget to try their signature Boatyard Mai Tai, which is a local favorite.

Looking for something more casual? Island House Tap and Grill is the perfect spot. This easygoing restaurant serves up delicious Latin street eats like tacos, ceviche, and stir-fries. Don’t forget to try their refreshing mojitos or margaritas.

For a fun and lively atmosphere, The Old Salty Dog Siesta Key is the place to be. This British pub serves up classic fare like beer-battered fish and chips and live music. Bring your furry friend along, as they’re welcome on the patio.

So, ditch the fancy prix-fixe menus and discover the hidden gems of Siesta Key’s mid-range dining scene. You’re in for a treat!

Cheapest Restaurants

Siesta Key’s sun-kissed beaches and vibrant life scream indulgence, but what if your wallet whispers frugality? Fear not, fellow treasure hunter! Unbuckle your expectations and prepare to tantalize your taste buds without breaking the bank.

To start off your culinary adventure, hook into happiness at Captain Curt’s Crab & Oyster Bar. Prepare to be boarded by an explosion of flavors at Captain Curt’s. Get ready to yo-ho-ho with a bottle or even a bucket of steamed peel-and-eat shrimp during their “Shrimptacular” Wednesdays. Feeling adventurous? The “Captain’s Catch” is a daily mystery box of fresh seafood, a delicious gamble your tastebuds will thank you for.

Next, you can reel in relaxation at Miguel’s Restaurant. Every Wednesday, their “Pasta Fiesta” lets you choose from an array of homemade pasta creations, each a symphony of taste. And if you’d like to feel the island breeze, the “Sunset Tapas” menu offers a delectable selection of bite-sized delights perfect for sharing with friends as you watch the sky set ablaze.

Another affordable and interesting waterfront restaurant in Siesta Key is Turtles Restaurant. Don’t let the unassuming exterior fool you. Turtles is a treasure trove of island flavors waiting to be discovered. Every Thursday, their “Lobster Luau” transports you to paradise with lobster tacos, tropical drinks, and live island music. Craving a taste of the mainland? Their “Burger & Beer” Mondays offer cheap classic comfort food.

For sumptuous breakfast bites visit Sun Garden Cafe. Tucked away in a tropical haven, this breakfast and lunch haven boasts wallet-friendly magic. Think fluffy pancakes drizzled with homemade syrup, juicy burgers stacked high, and fresh salads bursting with local goodness. Don’t miss their “Sunshine Special”, consisting of two eggs, crisp bacon, and fluffy toast, all for under $10, the perfect fuel for a day of island adventures.

 

Craving creamy goodness? Siesta Key is your oyster (Well, gelato!). Made in Rome Organic Gelato whips up handcrafted scoops of pure indulgence. Imagine velvety Madagascar vanilla bean or tangy mango sorbet, all made with fresh, local ingredients. Their “Small Scoop, Big Smile” deal lets you savor their creations for just $5, leaving you with a grin as wide as the beach.

For a taste of Italy without the plane ticket, head to Gentile’s Authentic Cheesesteaks. This hole-in-the-wall gem piles juicy meats, melty cheeses, and fresh veggies onto toasted rolls, creating symphonies of flavor. Their “Philly Phervor” special, overflowing with steak, onions, peppers, and provolone, is a steal at under $12. That said, prepare for flavor-induced happy tears.

Finally, end your budget-friendly feast with a sweet serenade at Meaney’s Mini Donuts. These bite-sized delights, fried to golden perfection, are dusted with cinnamon sugar and come in playful flavors like chocolate and maple. Grab a bag (or two!) for under $5 and share the sugary joy with friends and family. You can then watch the sunset paint the sky pink as you devour these mini masterpieces, the perfect ending to a budget-conscious, flavor-filled adventure.

So, ditch the fancy frills and embrace the delicious reality. Siesta Key’s culinary treasures await, beckoning you to indulge without breaking the bank. With these hidden gems on your map, you’re guaranteed to leave with a satisfied stomach and a happy wallet, ready to conquer the rest of your island escape.

Immerse Yourself in Siesta Key Bliss

Imagine sinking your toes into sugar-soft sand, the turquoise Gulf washing over your ankles. Breathe in the salty air, feel the warm sun on your skin. This isn’t a dream, it’s your reality at our stunning vacation rentals in Siesta Key.
Nestled along the pristine shores of Siesta Key, our vacation rentals promise an unforgettable escape into paradise. With a myriad of features and amenities designed to elevate your vacation experience, we invite you to indulge in luxury and relaxation like never before.

Step into our beautifully appointed accommodations, where modern elegance meets coastal charm. Each rental boasts spacious living areas adorned with stylish furnishings and breathtaking views of the Gulf of Mexico. Whether you’re lounging in the sun-drenched living room or unwinding on your private balcony, every moment is infused with tranquility and comfort.

Additionally, get ready to embrace the culinary delights of Siesta Key with our fully equipped kitchens, complete with state-of-the-art appliances and ample counter space. You can prepare gourmet meals with ease or savor the flavors of the local cuisine from the comfort of your own dining area. With everything you need at your fingertips, dining becomes a delightful experience to be savored and shared with loved ones.

You can also indulge in ultimate relaxation with our luxurious bedrooms and spa-inspired bathrooms. Sink into plush bedding and drift off to sleep to the soothing sounds of the ocean. Awaken refreshed and rejuvenated, ready to embrace another day of sun-soaked adventures. Our bathrooms offer a sanctuary of serenity, where you can pamper yourself with indulgent amenities and unwind in style.

Experience resort-style living with our unparalleled amenities, designed to cater to your every whim. Take a refreshing dip in our sparkling swimming pools, surrounded by lush tropical landscaping. Lounge poolside with a refreshing cocktail in hand or soak up the sun on the expansive sundeck. With our attentive staff on hand to cater to your needs, every moment is infused with unparalleled luxury and relaxation.

 

You can also stay active and energized with our state-of-the-art fitness center, equipped with top-of-the-line equipment and panoramic views of the Gulf. Whether you prefer a morning workout or a sunset yoga session, our fitness facilities provide the perfect setting to maintain your wellness routine while on vacation. Rejuvenate your body and mind and return home feeling refreshed and revitalized.

Explore the beauty of Siesta Key with our convenient beach access and complimentary beach amenities. Sink your toes into the powdery white sands and immerse yourself in the crystal-clear waters of the Gulf. From swimming and sunbathing to beach volleyball and water sports, there’s endless fun to be had just steps from your doorstep. Create unforgettable memories with loved ones against the backdrop of breathtaking sunsets and gentle ocean breezes.

Beyond your private oasis, get ready to discover the charm of Siesta Key Village, just moments away from our vacation rentals. Stroll along quaint streets lined with boutique shops, art galleries, and eclectic eateries. You can also indulge in the vibrant culture and laid-back atmosphere of this coastal community, where every corner holds a new adventure waiting to be uncovered.

Book Your Stay in One of Our Exquisite Siesta Key Vacation Rentals

At our vacation rentals, every moment is an opportunity to create cherished memories that will last a lifetime. Whether you’re seeking relaxation, adventure, or simply a moment of tranquility, our luxurious accommodations and unparalleled amenities provide the perfect backdrop for your dream vacation. Contact us to book your stay with us today and experience the magic of Siesta Key in style.

Florida’s Siesta Key is one of the state’s best vacation spots, offering delightful year-round weather, easy access to the Gulf, and numerous on and off-water attractions. Whether you want to treat your partner to a romantic couple’s getaway or surprise the gang with a riveting escape, Siesta Key has something for everyone. As you prepare for your Sunshine State holiday to this lovely gem, book your vacation rental with Rent Siesta Key and enjoy a seamless lodging experience in our luxurious properties. Here’s more on why you should book one an oceanfront Siesta Keys rental.

Top-Notch Amenities in an Oceanfront Siesta Keys Rental

A vacation rental should deliver the same comfort and convenience as your home. At Rent Siesta Key, all our Gulf front rentals feature excellent amenities, ensuring you and your fellow vacationers enjoy a cozy lodging experience. One of the first things you’ll notice once you walk in is the open plan concept living room, allowing for seamless movement. All living rooms have plush furnishings, beautiful decor, and large flat screens, affording ample luxury. Massive windows allow sufficient natural light into the space, creating a peaceful ambiance that boosts mood and enhances relaxation.

 

Unleash your inner chef in our fully equipped kitchens, featuring spacious countertops and numerous appliances for a seamless cooking experience. After a long day of exploring Siesta Key, enjoy a good night’s rest in modern bedrooms with cozy mattresses and clean linen. Each rental also features elegant bathrooms with plush towels, delivering a sanitary space for freshening up. Depending on your chosen property, you’ll have access to a private or community pool, giving an alternative space for a soothing dip beside the Gulf. Some rentals also offer hot tubs where you and yours can unwind before turning in for the night.

Easy Access to the Gulf

The Gulf’s picturesque emerald-green waters offer numerous on-water thrills. Our Siesta Key Gulf front rentals give you quick access to the Gulf, allowing tons of fun by the water’s edge. All our properties lie a few hundred yards from the beach, saving you the hassle of commuting or driving. Head out for a soothing swim in the warm waters or enjoy a relaxing stroll on the gorgeous white sands as you relish the pleasant Gulf breeze.

Proximity to the Gulf also gives you an easy avenue to parasailing tours, where you get to soar several hundred feet as you take in the lovely views of Siesta Key. Another popular Gulfside activity is dolphin-watching tours, where you head out to interact with these lovable marine mammals and witness them in their natural habitat. Rent a jet ski and explore the serene waters on a solo excursion, or book a guided tour and have a seasoned guide take you to the best spots. If you’re an angling enthusiast looking for a prized catch, book a fishing charter and test your angling skills as you aim to reel in one of the Gulf’s numerous fish species.

Soothing Year-Round Weather

There’s a famous adage that says seasons come and go, but not so much in Siesta Key. While most of the United States experiences the extremes of seasonal changes, Siesta Key remains nice and toasty all year long. Over the year, Siesta Key’s temperature varies from the low 50s to the high 80s, making it one of the best places to vacation.

The coldest season lasts nearly three months, from early December to early March, with temperatures averaging 74 degrees Fahrenheit. January is the barrier island’s chilliest month, with an average low of 54 degrees Fahrenheit, which is well above the countrywide average of 33 degrees. The delightful subtropical climate allows for riveting outdoor adventures, regardless of when you choose to visit.

Gorgeous Views

Picture waking up to picturesque sights of the Gulf as the sun’s bright orange-yellow hues slowly come into view. That’s the kind of experience you get from our lovely Gulf front rentals. Each home’s living room and bedrooms feature large windows that give you tranquil sights of the sand and sea. Watch the waves gently caress the shore while local seagulls soar in the breeze.

 

All our Gulf front rentals feature patios, offering a serene setting to enjoy the sweeping views. The patios have cozy seating or sun loungers to lay back as you soak in the sweet sunshine and take in the majestic sights. Most properties’ outdoor sections have adequate shade, allowing you to relish the views in a sheltered area without excessive exposure.

Proximity to Scenic Biking Trails

While Siesta Key is widely renowned for its beautiful beaches, the island also features multiple biking trails. At Rent Siesta Key, our Gulf front properties give you easy access to lovely biking trails, perfect for a peaceful afternoon cycling session. Walk to town for bike rentals, then peddle to the ten-mile Venetian Waterway Park Trail that traverses along both sides of the famous Intercoastal Waterway. Another popular biking route is the Legacy Trail, which starts southwards of Sarasota, passing eight rest stations before culminating in Venice.

For the best bike rentals in Siesta Key, look to Ride & Paddle. This renowned bike shop has been serving Sarasota and her neighbors since 1995, cementing its place as one of the island’s best places for a bike rental. They offer everything from beach cruisers to geared bicycles and electric bikes with pedal assist. Aside from bike rentals, you’ll also find helmets and locks for a safe peddling experience. Renting saves you the hassle of carrying your bike to Siesta Kay while offering quality selections for all your biking needs.

Convenient Location

All our Siesta Key Gulf front rentals lie within strategic locations, offering easy access to the island’s main attractions. The Gulf sits a few hundred yards from each rental, eliminating the need to commute to the water’s edge. Grab your cooler and beach chairs and seamlessly head to the shore for a relaxing day by the Gulf. Nearness to the water allows for umpteen aquatic activities, including parasailing, jet skiing, and swimming.

All our properties also lie close to the island’s business district, making it a breeze to explore the local attractions. Relish the local culinary scene, get the freshest produce at Siesta Key Farmers Market, or catch a live music performance at Siesta Key Oyster Bar. If you’re flying in, the Sarasota-Bradenton International Airport lies roughly 45 minutes from the island, making the commute to our rentals brief. Other social amenities like the Sarasota Memorial Hospital, Walmart, and Sky Zone Trampoline Park sit less than 20 minutes from the island.

Thrilling Food Tours

If you’re a food enthusiast looking to tickle your taste buds with delightful cuisine, Siesta Key offers several food tours. The Taste of Downtown Sarasota delivers an excellent culinary experience, perfect for a date night with your partner or socializing with family and friends. The three-and-a-half-hour tour includes a robust menu of eight to ten dishes, offering a unique dining journey you’ll remember for years.

The Sarasota Street Food Tour takes you through the island’s exciting street food offerings, where you’ll sample five or six food varieties from local vendors, stalls, and restaurants. You’ll discover hidden cuisines as you enjoy a laid-back experience of local gastronomy. The Twilight Sip and Dine allows you to indulge in local wine and cocktail varieties. The tour takes you through four eateries in Sarasota’s downtown area as you sip on the best drinks at each spot. Other popular food tours worth checking out include the Downtown Electric Bike & Food Tour and the Culinary Pairing Experience.

Luxury Shopping Centers

Shopping is a must-do while vacationing. It’s a terrific way to grab your favorite merchandise and souvenirs while promoting local retailers. Crossings at Siesta Key is one of the island’s most renowned shopping malls, offering multiple high-end stores, including Macy’s, Art Avenue, LensCrafters, and The Orchid Lady. Beach Bazaar has several shops selling beach gear, clothing, and souvenirs you can buy for yourself or a loved one.

St. Armands Circle lies between the Gulf and Sarasota Bay, offering over 140 deluxe boutiques, award-winning eateries, and exquisite art galleries in a picturesque European ambiance. Island Trader Boutique is highly regarded as Siesta Key’s best store for women’s attire, selling stylish accessories such as beach bags, hats, purses, and jewelry. Other popular shopping centers include Silver City Sarasota, Sunshine & Sand Hidden Treasures, and Foxy Lady.

Excellent Transport Network

An efficient transport network is crucial to enhancing the quality of your vacation experience. Siesta Key has a robust transport network, allowing for hassle-free movement within the island. The closest airport is Sarasota Bradenton International Airport, which lies 10.5 miles from Siesta Key, allowing you to fly into the island from any part of the US. Once you land, you can hire a rental and take the 19-minute drive down to Siesta Key via the North Tamiami Trail. For the best-priced car rentals, stop by AutoSlash and enjoy an expansive selection of automobiles, including compact, mid-sized, full-size, and luxury cars.

Once you’re on the island, there are several ways to get around Siesta Key. The Sarasota County Area Transit bus offers smooth commutes around town alongside the Siesta Key Breeze Trolley, which delivers free rides every 20 to 30 minutes. Siesta Key has 20 cycling routes covering 177.7 miles if you prefer getting around on two wheels. The trails feature a blend of paved and unpaved paths, with various elevation changes, making for exciting biking escapades as you crisscross the island.

Book Your Siesta Key Gulf Front Rental Today

Siesta Key is a vacation paradise promising riveting adventures and tons of fun. Spend the day at one of the island’s gorgeous beaches, relish the beauty of the Gulf on an exciting parasailing escapade, or connect with local dolphins on a memorable dolphin tour. If you prefer keeping the fun indoors, explore the local culinary scene and treat your taste buds to the island’s diverse cuisine, visit the famous South Florida Museum’s 60,000 gallon aquarium, or enjoy a relaxing massage at the Hands of Light Massage and Day Spa.

As you prepare for your Siesta Key escape, look to Rent Siesta Key for the island’s best Gulf front rentals. We offer multiple high-end properties by the Gulf, from cozy one-bed rentals for four guests to massive six-bed options for up to 16 people, giving you ample lodging variety to suit your travel group. All our Gulf front rentals feature top-notch amenities, including well-decked living rooms, fully-stocked kitchens, spacious bedrooms with clean, plush bedding, well-designed modern bathrooms with premium towels, and comfortable patios.

We have over 15 years of experience in the vacation rental industry, serving over 50,000 satisfied customers at the island’s most competitive rates. Contact us today to secure your preferred Gulf front rental and relish your Siesta Key getaway in exceptional luxury, comfort, and convenience.

A spring vacation on Siesta Key offers the perfect respite for winter tired travelers, providing sunshine, warmth, and a variety of events that will help visitors make memories they will never forget. From Easter egg hunts to architectural boat cruises, the beautiful weather encourages everyone, not just travelers, to get outside and experience Florida at its best. Play hard, revel in the near perfect temps, and come home every evening to Rent Siesta Key and relax in the comfort of our seasonal sanctuaries and explore the luxuries that we think all our guests deserve.

38th Annual Run for the Turtles, April 6

Sea turtles have been in existence for millions of years, roaming the earth with the dinosaurs, but today they are on the endangered list, with some varieties verging into the critically endangered lists, just steps away from becoming extinct. As such, we Floridians are constantly seeking ways to help increase their numbers, and with the proceeds from our 38th Annual Run for the Turtles, we are doing just that. Although you may not think of running during your vacation is all that fun, the views of sand and sea, your race t-shirt, and the knowledge that your $40 dollar entrance fee is going to such a worthy cause will ensure an adventure that you will never forget.

Siesta Key Parrothead Cruise, April 10

September 2023 was a sad month for parrotheads from all over the world, as it was the month that fans bid a final farewell to Jimm Buffett, and in April 2024, the Upper Midwest Parrothead Club invites you to cruise up the intercoastal with them to wear your favorite Parrothead gear while singing along to the music that is associated with so many of your memories. Boat drinks will be shared in memory of the great man himself, and the cruise begins at 1 PM, in front of CB’s Saltwater Outfitters located on Siesta Key.

North Siesta Key Architectural Kayak Tour, April 20

Some of Siesta Key’s most beautiful structures are private homes, not meant to be explored by tourists, but if architecture makes you happy and the thought of spending an afternoon kayaking the waters around Siesta Key brings you joy, this architectural kayak tour combines them both. Offering a chance to see the beautiful homes while paddling your way through calm waters, the tour, sponsored by Architecture Sarasota, begins at 2 and is scheduled to end at 4, is a wonderful way to enjoy two of your favorite hobbies.

4th Annual Taco & Tequila Crawl, April 27th, 1888 Main Street in Sarasota

Located just off Siesta Key, the town of Sarasota expands your chance of having a good time at a local event during your Florida getaway and the 4th Annual Taco & Tequila Crawl, taking place on April 27 from 5-10 PM is the perfect example. Offering drink specials at a variety of bars in Sarasota, (five in total) music, dancing, and, perhaps the best part of all, tickets that can be exchanged for three tacos, this will be the night you never remember, if you do it right, of course.

Mo & Mary Mac @ Siesta Key Wine Bar, May 3, 5138 Ocean Boulevard Suite C

Sometimes the best events are the simple ones, involving good music, good company, and in this case, very delicious and good wine. Mo & Mary Mac, a Virginia based musical group making their presence known in the south, play the laid-back tunes that make you want to dance, sing along, and close your eyes to be able to feel the beat even more and on this first Friday in May, our guests can sample sips of wines that come from all over the world.

Fresh Fridays, Downtown Sarasota

The first Friday of every month is known as Fresh Fridays in Sarasota, a celebration of the week’s end, featuring art, live entertainment, and delicious food provided by some of our favorite local restaurants. Starting at 7 PM, we can’t think of a better way to pay honor to the weekend than attending this fresh event that occurs in every month of the season.

Your Family Vacation with Rent Siesta Key

Not every event has to be one sponsored by a local business, especially as your favorite event may simply be your family vacation on Siesta Key. Spring is meant for families and our homes and condos are designed to be havens of fun and family and when you combine the two, we can promise an adventure that will may just make spring your most favorite holiday of all! Reserve your favorite Rent Siesta Key seasonal sanctuary today and explore the sunshine state from the most comfortable spaces on Siesta Key.

A Florida vacation is what all Spring Breakers dream about, and even if your idea of an exciting Spring Break involves helping your toddler construct a sandcastle at shore’s edge, a Siesta Key Spring Break vacation promises to be every bit as fantastic as you dreamed it could be, especially if you choose Rent Siesta Key for your celebratory sanctuary and follow the guidance we provide in this list of fun that can be had when spending your Spring Break vacation in our community. Featuring the best party spots, the most serene relaxation revelries, and the most exciting adventures, this list is a comprehensive guide to good times!

The Most Beautiful Beach in the World

We have visited many beaches over the years, and we always come away feeling disappointed because we know in our soul, our Siesta Key beaches are the most beautiful in the world. You don’t have to take our word on this, though; instead, we invite you to visit them yourself, starting with your Spring Break escape to our hometown. Don’t worry about having to skip any party time as you frolic in the surf, because alcohol is allowed on our beaches for everyone who is 21 or over. Sip margaritas from plastic cups, keep your beer chilled in your favorite beer koozies, and bring your boxed wine to your beach towel as your ear buds play your favorite tunes and the sun shines down on sugar white sand beaches and turquoise waters. This sand is also good for building sandcastles if you are a family person celebrating your own version of Spring Break.

Rum Runners for the Win

Every partier has a beverage they call their own, but the rum runners (and rum punches) of Florida are destined to become your new obsession! The recipe for deliciousness is simple, consisting of a variety of rums, liqueurs, and juices, with each of these fine establishments putting their mark on our favorite Florida beverage. The Daquiri Deck in Siesta Key Village may be known for its daquiris, but we promise their rum runners are equally fine, and Gilligan’s Island Bar & Grill offers a casually good time and rum runners you may forget if you sample too many. The Old Salty Dog Siesta Key is a pet friendly British pub serving pub grub and rum runners (they are famous for their margaritas as well, if you care to try that drink as well) and the MVP of Siesta Key (My Village Pub) will never let you down.

Making Mornings Bearable

After a long night spent sipping rum runners, you may find it difficult to get moving in the mornings, but the coffee served at these coffee shops promise to make mornings bearable again. Don’t let the name of Meaney’s Mini Doughnuts & Coffee House, 205 Canal Road, keep you from trying the best coffee and donuts in town, and don’t miss the opportunity to discover if your Mojo really will rise when you explore the offerings at Mojo Risin’ Coffee Co. (5251 Ocean Boulevard) 

The Party Begins

Now that you are relaxed, tanned, and well caffeinated, it is time to check out the night life on Siesta Key, and we have compiled this list of some of our favorite party spots that will add extra sparkle to your celebration. The Beach Club, 5151 Ocean Boulevard, is open every day from noon until 2 AM and provides live music, DJs, and a happy hour that takes place every day from noon until 7 PM. Their special events, including an annual bikini contest, add even more fun to your party adventures. Captain Curt’s Sniki Tiki Bar & Live Entertainment, 1204 Old Stickney Point Road, promises to be rocking every night of your stay, offering an outdoor patio, live music, and late-night dining that will help sop up the alcohol in your system. The Blasé Café & Martini Bar, 5283 Ocean Boulevard, offers live music, a dance floor, and another option for partying the night away on Siesta Key, ensuring that your Florida getaway will be filled with multiple entertainment options.

The Best Moments Are the Ones Spent with Rent Siesta Key

When the last note has played and the final sip of rum runners has been finished, coming home to your Rent Siesta Key Spring Break sanctuary will bring comfortable adventures worthy of airing on the highlight reel of your Florida memories. Sleep in late on premium beds topped with soft linens, shower away the worst of your hangover grogginess in our comfortably appointed bathrooms, and yes, raise a toast to the sunset from the balcony of your holiday hideaway. Even if you haven’t been partying like the college student you once were, (remember those days?) our rentals will provide a haven of peace and all the comforts of home. Contact us and reserve your favorite escape today!

A Florida vacation spent on Siesta Key in one of our Rent Siesta Key vacation escapes promises to be an exciting and most comfortable adventure and even as our properties all offer fully equipped kitchens, chances are you will want to explore the epicurean landscape of the Key and surrounding areas. There are plenty of restaurants to visit during your stay, but perhaps this will be the trip in which you indulge your true food loves, the ones served from the window of a food truck that roams the streets seeking hungry people to feed. No longer a construction site’s dirty little secret, food trucks have become popular for their unique and gourmet food choices and this guide to the top food trucks to try during your Siesta Key vacation is sure to help you satisfy any food craving.

The Porthole Grille

It only makes sense to start our taste tour with a visit to the Porthole Grille, a local food truck serving a seafood-centric menu in the Siesta Key Village area. Their seafood menu offers the standard and the unusual, including tender flame grilled octopus, but they also feature land fare such as burgers, dogs, and chicken. One of our favorite purchases from the Porthole Grille, however, is neither land nor sea but the sweet taste of their chocolate dipped Caribbean key lime pie on a stick, a treat that we recommend to all. 

Sharky’s Snack Shack

Sharky’s on the Pier is a popular restaurant in this area and Sharky’s Snack Shack, a food truck that sells its wares from Siesta Beach is even more so. Offering a little bit of this and a lot of that, their menu is a beautiful blend of seafood, burgers, tacos, and rice bowls, ensuring that everyone will find something that tickles their fancy.

Siesta Pops

When your sweet tooth is demanding to be acknowledged, Siesta Pops is happy to oblige. Providing a dessert menu that includes mini donuts, acai bowls, and the most delicious of hand-crafted gourmet popsicles, Siesta Pops is a local staple at farmers markets and food truck festivals.

Mouthole Barbecue

The smell of smoked meat and spicy barbecue sauce will get your mouth watering before you even catch your first glimpse of this savory food truck, and although it is primarily based in Sarasota, you won’t have to venture far from Siesta Key to enjoy its food. One of the most popular food trucks in the area, Mouthole is known for taking part in events all over Sarasota, including, the celebration of National Food Truck Day that takes place on June 30th.

Baton Roux

As you may have guessed, Baton Roux’s menu comes straight from the bayous of Louisianna, featuring all your Cajun favorites. Jambalaya, gumbo, red beans and rice, and the sweetest of all treats, beignets can be purchased off this roaming food truck, all destined to make your taste buds stand up and cheer. The food truck, based out of Bradenton, also offers a selection of frozen foods that guests can take back to their Siesta Key home sweet vacation home to heat up and enjoy with the greatest of ease.

Willy-Yums

Another Bradenton based food truck, Willy-Yums puts a brilliant spin on everyone’s favorite handheld, the hotdog. Dining out can be expensive, but this charming food truck offers incredible deals that will make it easy and inexpensive to feed your hungry family. On Tuesdays through Thursday from 3-6 pm they provide what they call Happy Hour Afternoon Delight, a special meal box filled with fries, chicken and a fully loaded hotdog destined to sate the largest of appetites.

Taqueria El Milagro

Our next to the last food truck we want to discuss today is also based out of Bradenton, but without tacos can you really consider that you have lived? Taqueria Milagro roams the area providing authentic breakfasts and lunch for residents and visitors of Bradenton, Sarasota, and of course, Siesta Key. 

Spice Boys Kitchen

Another international delight, this one based out of Sarasota, Spice Boys Kitchen serves the best Israeli food in the state. This Mediterranean food truck offers something called a sabich, a pita stuffed with eggplant, potatoes, egg, tahini, and a pickled mango sauce, this savory treat is destined to become your newest obsession and we hope you can find something equally delicious when you return home to real life!

Enjoy Your Food Truck Meals in Comfort and Style

Although all the trucks will more than likely provide a place to sit and dine, you may be more comfortable bringing your food back to your Siesta Key sanctuary to enjoy in comfort and style. Still want to eat outside? Take your meal to the patio to watch the sun set over the horizon as you devour each and every bite. Reserve your favorite escape and contact us today!

Love is the most beautiful feeling of all and your special Valentine deserves a getaway that helps express that love more clearly. Deserving beach days in the middle of the winter, comfy nights filled with snuggles and shared secrets, and adventures of the most romantic kind, you want the world for her and at Valentine’s Day you can gift her with one of the most romantic segments of the world, a stay in Siesta Key! Rent Siesta Key invites you to explore our cozy love nests with this guide to spending Valentine’s Day 2024 on our white sand beaches and in our cozy holiday hideaways!

Breakfast in Bed

Yep, we are going there. The reason traditions hold is because they work and nothing screams romance louder than awakening to your love bringing you all the breakfast treats you enjoy. Our fully equipped kitchens provide a cheerful spot in which to scramble eggs and blend mimosas, but if cooking isn’t your strong point, food delivery services will bring the meals you crave straight to your doorstep!

A Symbol of Forever

Now you might be wondering if your gift of a Siesta Key vacation isn’t enough and that the memories should last forever, and you will be absolutely correct. However, a gift given on the actual holiday is always a nice gesture, making a visit to linkxluxe, 532 S Pineapple Avenue in Sarasota, a truly excellent idea. Specializing in the latest romantic trend, permanent jewelry, the memories of your Valentine’s Day escape to Siesta Key may fade or blur over the years, but the shine on the gold bracelet around her wrist (or his!) will never dull!

Where the Dolphins Play

There is nothing more beautiful than spending a few hours on the clear waters that surround Siesta Key watching friendly and chattering dolphins frolic in the surf and Siesta Dolphin Tours, (941) 926-3131, provide that service amazingly well. Taking you to the best spots on the Gulf where the dolphins are always playing, the dolphin tours provide an incredible naturally romantic experience, especially if you choose one of their sunset cruises, combining fire in the sky with laughter in the sea, while adding a little extra dose of love to your heart!

Making Memories with Photos

The world has come to the realization that professional photos aren’t just for families to document the growth of their children over the years, instead, we are hiring someone who can take the good photos to document all aspects of our lives and the Vintage Pea Photography Company, (941) 961-9654 would love to document this segment of your love story. Using the white sand beaches of Siesta Key as a backdrop, perhaps the only thing more beautiful will be the light shining from your Valentine’s eyes as you stare into them.

Sunset Walks on Siesta Key Beach

The sunset dolphin tour is destined to be a winner, but what if you aren’t willing to share your Valentine with strangers on a cruise? A simple walk along the shore’s edge at sunset will help you keep her to yourself and perhaps provide the perfect moment to pop the forever question. She has walked alongside you for years and you have reached the conclusion that you want to spend forever enjoying adventures like these and as the sun sinks below the horizon, setting the sky alight with its fiery colors, chances are all she will notice is you kneeling before her on bended knee, perhaps encouraging more sunset walks during your stay on Siesta Key.

A Meal to Remember

No Valentine’s Day celebration would be complete without a romantic meal topping off the day and in Siesta Key, that meal must be held at The Cottage. Located at 153 Avenida Messina, the cottage provides a beautiful glimpse into Florida, offering an outdoor patio with trees filled with twinkle lights, the occasional guitarist strumming and singing softly in accompaniment, and a menu filled with seafood-centric dishes, all prepared with a Japanese flair. You don’t need to dress up to enjoy this romantic restaurant and you won’t have to break the bank. The Cottage is a perfect example of the casual and laidback Florida vibe and the meal you enjoy here will be unforgettable.

Fall in Love with Rent Siesta Key

Every moment will be your favorite when you choose one of our romantic condos or cottages to make your home sweet vacation home over Valentine’s Day. Relaxing on balconies or patios overlooking the turquoise waters of the Gulf of Mexico, the roar of the sea providing a serene accompaniment to your quiet conversations. Sleeping in late every morning, staying up later every night, and filling the in between moments with hand holding, kisses, and the sharing of secrets, hopes, and dreams. Reserve your favorite Valentine’s Day escape today! Contact us today!