×

  • This field is for validation purposes and should be left unchanged.

The year-round sun and warmth of Florida is the perfect destination no matter what time of year you want to get away. The decision to head to Florida may be simple, but you’ll also need to plan things like where to go, all the fun and exciting activities you’ll do, as well as where to stay so you can do it all in comfort. Beautiful Siesta Key is a choice that will give you unforgettable memories, sun, and fun throughout your stay. When you search for your perfect place to stay, you’ll want something that reflects the fun, excitement, and relaxation you look forward to throughout your stay.

Crescent House is a 3-bedroom, 3-bathroom Siesta Key vacation home with room for up to six guests. From the time you walk in, you’ll feel as if you’ve stepped into a home away from home while still being close to all the restaurants, shops, attractions and more you’ve come to Siesta Key to experience.

Highlights:
• Central A/C
• Master Bedroom (King) + ¾ Bath
• Newly Remodeled
• Close to the Beach

Key to Relaxation

Guest looking to relax in style on their respite to Siesta Key will find all they desire and more in Crescent House. Stylish furnishings and finishes can be found at every turn, in bedrooms and living spaces, too. Crescent House is just moments away from the beach and crashing waves of the Gulf of Mexico and everywhere else you want to be on the island. Enjoy exciting activities, bars, shops, beach gear, bike rentals, and countless other attractions that are sure to keep you busy throughout your stay.

Exterior Features

Feel yourself relax from the moment you arrive at Crescent House. Its beachy blue exterior and modest front project a calm and soothing experience. A simple entry opens up to the garage for an even more private entrance to the Siesta Key vacation home, while a paver walkway leads through a gate and into the lush green grass of the yard back entertaining area of the home. Mature vegetation blocks the beat of the Florida sun and offers extra privacy. A simple patch of grass provides space for the kids to run around and burn off energy safely. An entrance through the yard leads to the garage. Follow the patio around to a white gated fence for access to your own backyard oasis. A large in-ground pool surrounded by decking in the same stone as the patio is the major feature of the ground-level outdoor space. A covered patio plays host to simple outdoor seating and boasts gated entry to the garage. Grill up the catch of the day or another favorite dish on the built-in grill and enjoy the meal on the patio at the bistro-style outdoor furnishings for two, or in the outdoor seating for four shaded by beautiful palm trees. Head up a short spiral staircase to a large covered and enclosed balcony with outdoor dining for six. A spiral staircase on the balcony leads you up to the most spectacular outdoor space the home offers, a rooftop deck where you can look out over the neighborhood or watch the sunset.

Interior Amenities

The main living level is on the second level of the home. Wood floors spread throughout the home, in living areas and bedrooms. Take the stairs from the lower level to arrive in a living area decorated in cool colors that hint at the sand and water of the nearby beach. A dining area for four greets you and spreads out into a living area decorated with a comfortable couch and chairs in muted colors. The seating is arranged around a colorful area rug and faces the wall-mounted flat-screen TV and a fireplace. When hunger strikes, head to the fully equipped kitchen featuring high-end stainless steel appliances and granite counters. The chef of the group will enjoy plenty of prep and storage space with expansive counters include a large kitchen island with farm sink, storage, dishwasher and wine fridge as well as seating for six spotlighted by pendant lighting. The enclosed balcony is accessible from the living area.

When the day is done retreat to a private bedroom, all of which have their own flat-screen TV. The master boasts a vaulted ceiling, plenty of natural light from windows, and a beach theme. Rest your head in the king-size bed or read a book in the wing-back chair or take advantage of private access to the covered balcony. Rinse off the sand and salt or prepare for the day in the luxurious master bath, which features expansive counters and ample storage space on the double-sink vanity. Step into a luxury frameless shower with multiple shower heads and controls, as well as heat floor and towel racks for a spa-like experience. The first guest bedroom is upstairs and boasts a queen bed, his and hers closets, and plenty of natural light from multiple windows. The en suite bath is a full bath with a tub/shower combo and single-sink vanity. The second guest room is located on the first floor and boasts a queen bed and an en suite bathroom with a shower and pedestal sink.

Contact Us and Book Your Siesta Key Vacation Home

No matter when or how long you plan to stay on Siesta Key, Crescent House will provide all the fun, relaxation, and excitement you’re looking for and more. Contact us today to book a stay full of memories that will have you coming back time and time again!

The warmth and sun of Florida is a major attraction any time of year. Kick-off summer the right way with a Memorial Day trip to that fun and sun you won’t soon forget by heading to Siesta Key. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities there are to do and see. With water temperatures already pushing toward the 80s and air temperatures in the mid-80s, you’ll enjoy every moment.

Beach Time

An island vacation without a visit to its beaches is virtually unheard of. You and your group are moments away for the luscious sand and vibrant waters of the Gulf of Mexico wherever you are. Fill the cooler, grab the beach gear, and stake your territory with blankets and umbrellas and prepare for a day of lounging on the shore, or a dip in the Gulf of Mexico.

Snorkeling

Snorkeling is a great way to get in the water and explore the area. Whether you rent gear from a local shop and head out on your own or book a charter tour, it’s a magical way to see the underwater world surrounding Siesta Key. Adventurers looking to make their own fun should try Point of Rocks, a spot known for tide pools, moss-covered rocks, and sea life in an easily navigable area. If you’ve been missing the group vibe, charter a boat with Key Life Charters where you can bring your own snacks, including adult beverages. Expand your snorkeling adventure with them by adding experiences like sightseeing, dolphin and wildlife spotting, and more.

Parasailing

Gain a whole new perspective on where you’ve chosen to spend your Memorial Day and sail high over the water with Parasail Siesta. You’ll take off from the deck of their specially designed and USCG-approved parasailing boat to fly high above the waters of the Gulf. Reach heights up to 500 feet in the air! Keep watch on the water from your bird’s eye view for dolphins, turtles, manatees, stingrays, and other sea life. Stay dry throughout the flight or wear your bathing suit for a refreshing dip in the water before flying up again to come down safely on the deck. Bring your waterproof or disposable camera to capture the memories from your perspective. Parasail Siesta takes several professional digital camera pictures of your flight and will provide you with a memory card at the end of the trip so you can develop your pictures at a later time. Rides are approximately 15 minutes of air time, but the whole excursion duration depends on the number of fliers.

Paddleboard Lessons

The warmer water and air temperatures of Siesta Key Memorial Day weekend mean more time in the shimmering waters of the Gulf. Stand Up Paddleboarding (SUP) is a popular water activity that anyone can try. If you’ve never done it before, take a lesson with Siesta Key Paddleboards. They offer daily lessons at Turtle Beach Park, as well as rental gear for those wanting to strike out on their own. If you’re confident in your skills, book a guided tour of the various waters around the island, both Sarasota Bay-side and Gulf-side.

Bicycle Rentals

Siesta Key has a land area of just 2.4 miles, so there are bound to be areas where a rental car just can’t go. Instead of trying to see everything by car, get some exercise by exploring the many walking and biking trails that bring you closer to those sights inaccessible by car. You can rent bikes for everyone in the group. Single-seat bikes without gears (a.k.a. cruisers), tricycles for extra balance and basket space, children’s bikes, adult bikes with baby seats, or take a romantic ride on a bicycle-built-for-two! Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.

Siesta Key Memorial Day Fun

When you book your fun-filled getaway to Siesta Key, you won’t be hard-pressed to find activities to fill every minute of every day while you’re here. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the day is done, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or romantic getaway all the way up to six-bedrooms for a Memorial Day reunion with friends or family.

Contact us today to book your Siesta Key Memorial Day getaway and make memories to last a lifetime!

If you’re planning a break around the Easter holiday, the perfect spring temperatures of Siesta Key is a wonderful environment for your getaway. The island hosts Easter activities like brunch and Easter egg hunts in addition to many year-round activities to choose from to keep you as busy as you want to be for the entire time you’re here. Whether you’re here with friends or family, an intimate break with your sweetest or enjoying a much-needed family or group reunion, you’ll find something for everyone during Siesta Key Easter.

Trolley

There are several ways to get around Siesta Key to see and do the things that will create lasting memories for everyone. You could pile everyone in the car and drive around, potentially spending more time in the car driving and hunting for parking than enjoying your vacation, rent bikes, or walk to get to all the sights, nooks, and crannies where cars just won’t fit. Save gas and stay pumped full of energy for the day’s adventures when you take the Siesta Breeze Trolley. The trolley offers free round trip transportation service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between. Travel the length of the island and back or hop off and wander around the various stops.

Dolphin Cruise

Head to Siesta Key Marina and you’ll see the many charter boats and cruises that aim to give you a special experience on the waters surrounding Siesta Key. Fishing excursions, snorkeling or SCUBA, and more are available. For something a little less adrenaline-pumping, choose a dolphin cruise. Of course, you can ‘ooh’ and ‘aah’ at dolphins and other marine wildlife safely from the shores of Siesta Key. An up-close look from a chartered tour boat will give you new appreciation for the majestic mammals. You’ll see more than dolphins! Keep your eyes open for manatees, rays, and even whales – they use the warmer waters of Florida during mating season. Any of these beautiful sea creatures might even come near the boat to swim alongside!

Parasailing

April air temperatures can get as high as the 80s, but water temperatures in the low 70s may still be too cool for some to enjoy the water for long. Enjoy the warmer air and cool sea breezes while you sail high over the water. Parasail Siesta offers parasailing experiences to the residents and vacationers of Siesta Key. You’ll take off from their specially designed and U.S. Coast Guard-approved parasailing boat and fly as 500 feet over the waters of the Gulf of Mexico. You’ll have a bird’s eye view of dolphins, manatees, stingrays, turtles, and many other species of sea life. You can choose to take off and land without getting wet, or dip down in the water momentarily before rising back up to come down safely onto the boat deck. Rides are approximately 15 minutes. You can bring your waterproof or disposable camera to capture all the memories from your point of view, from take-off to landing, but the company also takes several professional digital camera photos and will provide you with a memory card so you can develop pictures at your leisure once you reach shore.

Easter Brunch

If your vacation plans don’t include cooking an Easter meal, several of the many restaurants of Siesta Key offer Easter brunch or dinner. You’ll love mouth-watering meals prepared by the many and varied culinary talents the island has to offer. As about reservations and dietary restrictions like gluten-free, as special holiday meals may have limited offerings.

Sunrise Church Services

Greet Easter morning at a sunrise church service. The island’s churches offer indoor services, but for an Easter service like no other, check out the Siesta Beach Sunrise Service. The island tradition takes place at Siesta Key Beach near the pavilion and is hosted by Pine Shores Presbyterian Church. Bring a beach blanket or chairs. Contact the church for more information.

Easter Escape in Florida

When you and book an Easter getaway with Rent Siesta Key, you won’t be short on fun special Easter or year-round activities to fill your time. From church services and brunch to island fun like parasailing, you’ll be able to build an Easter getaway that is uniquely yours with memories to last a lifetime. For a small family or couple on an Easter respite, enjoy a one-bedroom unit. The bigger your group gets the larger accommodations you’ll need – Rent Siesta Key has units as large as six bedrooms! After you’ve savored Easter brunch, and for any other meal during your stay, prepare your favorites in your unit’s fully equipped kitchen. Enjoy the meal in a spacious dining area or take the meal outside to a balcony or patio. At the end of the day, relax in a private bedroom, or pop some popcorn and watch a movie. Choose a premium luxury unit for stainless steel, high end appliances, a fireplace, plush furnishings and even a private pool in some units.

Contact us today to book your Easter getaway hopping with memories of a lifetime!

A getaway to the warmer climates of Florida and its many beaches is the perfect way to relax and de-stress. If you came with your sweetie to Siesta Key, you’ll find plenty to do and see. You’ll find romance with a quiet dinner for two or couples massage, but when it’s time to amp up the fun, let loose and maybe dance the night away, you need to know where to go to find the hottest Siesta Key hot spots.

Gilligan’s Island Bar

You won’t find The Professor or Mary Ann here, and the only three-hour tour that may embark from here is a tour of the tasty food, cocktails, and entertainment you’ll find. A hotspot on Siesta Key for twenty years, you can spot their tiki bar with its thatched tiki roof from the street. Whether you start or end up here, you’ll find amazing food and drink with a Florida beach vibe like no other. If you’re hungry, food orders are available from the VW Bus parked in front of the kitchen. Inside, surfboards, palm trees, and other beach décor dominate. Order your tropical libation, like a daiquiri, pina colada, or mojito and sit back and watch the game on a flat-screen TV or head outside to the back beach patio. Until 10 p.m. you can dance to live music from local talent. Hours are 11 a.m. -2 a.m. Monday-Saturday and 12 p.m. -2 a.m. on Sunday. Please wear a mask upon entering and while not at your seat.

Pi Craft Beer & Spirit

Pi Craft Beer & Spirit is open late on the weekends, and when the weather is right hosting live music from local musicians. It’s the place on Siesta Key to have fun, eat good pizza and Italian favorites, and sample beers on tap, many of which are made in the USA. Dance the night away and enjoy local brews like the “Intercoastal” or “Circus City” or visit the west coast with the “Hazy Little Thing” created in Chico, California. Wear your mask to get in the door and when moving around the establishment but enjoy your drinks and meal mask-free.

Siesta Village

Much of Siesta Key’s hotspot’ fun is located in and around Siesta Village. You’ll find bars, pubs, restaurants, and more that offer live music and touches of the island’s tropical vibe. If you’re visiting Siesta Key during spring break time, much of the entertainment from these places spills out onto the beach with competitions and contests that take advantage of the island’s beautiful weather, sand, and the waters of the Gulf of Mexico. You’ll find a place –or places to dance the night away to your favorite tunes and enjoy delicious food and drink while you make the most of Siesta Key hotspot-hopping vacation.

Daiquiri Deck

With two locations on Siesta Key, Daiquiri Deck is a great way to start your night of bar-or club-hopping. Order any one of their margaritas, specialty shots, many drink features, or of course daiquiris. Choose from a list of flavors. If you’re feeling the Florida heat, order one of their famous frozen daiquiri combos, like the “Bat Sh*# Crazy” –their strongest combination, or the “Patriot Missile” –a red, white, and blue celebration filled with Electric Lemonade, pina colada, and strawberry daiquiri flavors and topped with light rum. There are mocktails for your designated driver, too. Balance out the drinks with delectable bites like seafood, salad, sandwiches, or burgers while you enjoy live music from local talents. If you didn’t finish your daiquiri before your group says it’s time to move on, put it in one of their Daiquiri Deck tumblers before heading out. You’ll need a mask to get in the door and for moving in public spaces, but you can enjoy your private time mask-free.

Date Night Hotspots on Siesta Key

When you book your fun-filled getaway to Siesta Key, you won’t be hard-pressed to find activities to fill every minute of every day. With many date night Siesta Key hot spots, you’ll find something to do to keep the fun rolling throughout the day and well into the night. Fuel up before hitting the town by preparing a nutritious and yummy meal in the fully equipped kitchen of your vacation rental by Rent Siesta Key, many with stainless steel appliances. Relax in a private bedroom, or if all the hotspot fun gave you a second wind, spread out with some popcorn to watch a movie, or enjoy time on a deck or patio. Choose a premium unit for perks like a fireplace, double ovens, and flat-screen TVs. From an intimate experience, we have one-bedroom units for you and your sweetheart all the way up to a six-bedroom great for a couples’ getaway.

Contact us today to book your Siesta Key getaway!

Enjoy yourself to the fullest with a luxury escape to Florida and Siesta Key. The state’s year-round beautiful weather and many luxury activities to choose from will keep you as busy as you want to be for the entire time you’re here. From playing in the water or on it, to exploring every inch of the island, your perfect vacation luxury vacation is waiting.

Paddleboard Lessons

If your Siesta Key luxury getaway comes when the waters of the Gulf are a little warmer, you’ll want to take part in the various activities in and on the water that requires getting more than just your feet wet. Stand-up paddleboarding is a popular activity everyone can learn and enjoy. Enjoy the luxury of private lessons or a private, guided tour of the island’s waters, both Sarasota Bay-side and Gulf-side.

Fishing

There are several companies on the mainland that charter private fishing tours, but if you want your captain to navigate like a pro through Siesta Key waters, check out Siesta Key Fishing Charters for a company that knows the waters here best. All of their charters welcome anglers of all ages and abilities. They have inshore, nearshore, and offshore adventures, with trips from four to eight hours. Ask about Florida fishing license needs when calling to book.

Dolphin Cruise

You can ooh and aah at dolphins and other marine wildlife from shore. You could also choose the luxury of a private, up-close view from a chartered tour. Visit Siesta Key Marina and choose from any number of boats that will have you out in the waters and getting a closer view of dolphins, manatees, and even whales at certain times of the year. They might even come near the boat to swim alongside!

Spa Day

Relax and unwind in luxury with a massage or other spa service. Siesta Healing at the Holistic Spa and Wellness Center will have you feeling relaxed and rejuvenated so you can enjoy the rest of your fun-filled, luxury getaway. Choose from an array of facials, massages, oxygen skincare, reiki, and more to complete your day of luxury pampering and relaxation. You’ll enjoy soft music, the calming scents of eucalyptus and lavender, comfortable lighting, and all the right notes for total relaxation.

Summer House Steak & Seafood

Don’t let the name fool you. Summer House Steak & Seafood is a year-round establishment on Siesta Key, serving tasty and luxurious dishes that will make your mouth water to the last bite. Choose from soups, salads, and appetizers to whet your whistle in anticipation of the meal to come, like certified Angus steak or pork chops. Have a taste of the sea with colossal lobster tail, blackened Gulf grouper, or Scottish salmon. You’ll find something to tickle your taste buds.

Sunset Cruise

Sit back in luxury as someone else pilots the boat. Watch the sunset as the captain navigates you through the waters surround Siesta Key, in search of dolphins and other marine life including manatees and aquatic birds. Sip on an adult beverage as you take in the beautiful Florida coast and Gulf waters as the sun sinks below the horizon to end any day of your stay.

Snorkeling

Enjoy the luxury of a private undersea tour with Key Life Charters. Snorkeling is a great way to see the underwater world that surrounds Siesta Key. You can bring your own snacks –and even adult beverages. They have custom packages so you can build your own experience, from just snorkeling to additions like sightseeing, dolphin and wildlife spotting, and more. If you’re looking to strike out on your own, rent some gear and head to Point of Rocks, where you’ll find tide pools, moss-covered rocks, and sea life in an area that’s easily navigable and only five feet deep!

Luxury Escape in Florida

When you decide and book a Siesta Key luxury getaway with Rent Siesta Key, you won’t be short on fun, luxurious activities to fill your time. From spending the day lounging at the beach to spending the day lounging in your vacation rental, or getting pampered at the spa, you’ll be able to build a luxury getaway that is uniquely yours with memories to last a lifetime. Enjoy a one-bedroom for a more intimate experience, all the way up to six bedrooms for a large family or family reunion full of luxury for everyone. For more privacy, choose a single-family home. Many rentals include private garages. If you don’t want to go out, make a luxurious and tasty meal in your unit’s fully equipped kitchen. Enjoy the meal in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom, or pop some popcorn or grab some snacks and watch your favorite movie or TV show. Choose a premium luxury unit for stainless steel, high-end appliances, a fireplace, plush furnishings and even a private pool in some units.

Contact us today to book your luxury-filled Florida getaway in Siesta Key!

Whether the kids are on a break from school or it’s a surprise getaway, you’ll want to gather the family young and old and head to Florida and enjoy Siesta Key activities. The state’s year-round beautiful weather and many family activities to choose from will keep everyone busy for the entire time you’re here. From playing in the water or on it, to exploring every inch of the island, your perfect vacation is waiting.

Paddleboard Lessons

Take your family vacation at a warmer time of year and enjoy water sports that require getting a little more than just your feet wet. Stand up paddleboarding is a popular water activity for the whole family. If you’ve never done it before, a lesson may be in order first. Siesta Key Paddleboards offers paddleboard rentals as well as daily lessons at Turtle Beach Park. Once you’re confident in your skills, book a guided tour of various waters around the island, both Sarasota Bay-side and Gulf-side.

Beaches

An island vacation without a visit to its beaches, no matter the time of year, is always a must. Pack up the family and your beach gear and make the short trip to the sand. Dive into the beautiful waters of the Gulf of Mexico or watch the kids play in the waves or build sandcastles while you work on your tan.

Fishing

There are several companies on the mainland that charter fishing tours but check out Siesta Key Fishing Charters for a company that knows the waters of Siesta Key best. All of their charters are family-friendly, and they welcome anglers of all ages and abilities. They have inshore, nearshore, and offshore adventures, with trips from four to eight hours. Ask about Florida fishing license needs when calling to book.

Dolphin Cruise

You might be able to spot dolphins and other marine wildlife from shore, but nothing beats an up-close view. Visit Siesta Key Marina and choose from any one of their charter tours, many with family-friendly atmospheres that welcome children and adults of all ages. Spot dolphins, manatees, and even whales at certain times of the year as they come near the boat to swim alongside.

Bicycle Rentals

Leave the car at your accommodations, gather the family, and head out for some exercise and to explore the many walking and bike trails that let bring you up close to the sights of the Florida Keys that aren’t accessible by car. Many rental companies are available and will have a bike to fit the needs of each family member. You can rent single-seat bikes with or without gears (also known as cruisers), tricycles for added balance and basket space, a bicycle built for two, and even children’s bikes or adult bikes with baby seats. Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.

Trolley

There are several ways to get around Siesta Key. Pile in the car and drive around, hunting for a parking spot at your chosen destination, biking or walking to get to the nooks and crannies where cars can’t go, or saving energy –yours and your rental car’s –by taking the Siesta Breeze Trolley. It offers free round-trip service from Siesta Key Village all the way to the southernmost part of the island, and many places in between.

Family Fun Siesta Key Activities

When you and the family book a getaway with Rent SiestaKey, you won’t be short on fun, family-friendly activities to fill your time. From spending the day lounging at the beach to spending the day lounging in your vacation rental, you’ll be able to build a family getaway that is uniquely yours with memories to last a lifetime. Relax and unwind in a private vacation rental after a fun-filled day with the whole family. Enjoy a one-bedroom for your small family, all the way up to six bedrooms for a large family or family reunion. For more privacy, choose a single-family home. Many rentals include private garages. If you don’t want to go out, make a family meal in your unit’s fully equipped kitchen, which may include stainless steel, high-end appliances. Enjoy the meal in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom, or gather the family, pop some popcorn, or grab some snacks and watch your favorite family movie. Opt for a premium unit which may include perks like a fireplace, double ovens, flat-screen TVs, private pool –some even screened in for added protection from the hot Florida sun. Include the whole family by asking about select rentals that allow your fur babies to stay.
Contact us today to book your family fun Florida getaway on Siesta Key!

Sometimes the first snowfall of the year is absolutely magical. Other times, it’s the sign that it’s time to book a trip somewhere warm and sunny. When you’re an adventurer that prefers to leave snowy getaways to others and likes to focus on the sand, sun, and emerald waves, then booking a winter trip to Siesta Key, Florida is a fantastic choice this year. Planning a fun, refreshing, and exciting getaway to Siesta Key in the heart of winter isn’t hard to do. This part of the state enjoys year-round sunshine and wonderful weather with the winter boasting daily temperatures in the mid-70s. For travelers, this means summer-inspired activities can be enjoyed well into January, February, and beyond. When you’re looking for some top winter adventures to round out your itinerary, the following are just a few of many winter in Siesta Key options to enjoy.

Check Out Sunset Beach

When you can’t wait to spend plenty of time outside and have a heart for sun-soaked moments, enjoying time at Sunset Beach is a must. This vibrant stop tops many beach hoppers’ lists and is known for its chalk-white sands just as much as its boardwalk. Whether it’s a stroll along the sand, time in the water or an afternoon of sunbathing that has you excited, Sunset Beach is a welcoming and scenic place to enjoy it all. As an added bonus, this beach sits within proximity to a number of restaurants and bars for times when you prefer to follow up your beach moments with a side of something savory.

Siesta Key Beach Playground & Pavilion

While Sunset Beach is a great option for adults looking to balance out flavor and beach fun, those that are traveling to Siesta Key with little ones in the winter and needing a place with options for all ages will love swinging by Siesta Key Beach during their stay. Situated just off Beach Road, Siesta Key Beach is a beautiful locale for those that love to linger on the shoreline. It also includes access to a fun playground for little ones with a need to burn off some excess energy! At Siesta Key Beach, kids can be creative with their imaginations while adults soak up the sun. Nobody ever has to be far from one another to make the most of a fun afternoon. Siesta Key Beach also hosts a large pavilion if you’re planning on packing a picnic lunch for the journey. Be sure to pack your snorkel gear as the waves at Siesta Key Beach beckon to families to hop in and explore under the waves together as well.

Siesta Key Fishing Charters

On-the-sand fun is plentiful for the winter traveler to Siesta Key, but there’s something exceptional about time spent on the water. Those that are looking to enjoy a guided angling experience can find exactly what they’ve been searching for with Siesta Key Fishing Charters. Headquartered in Sarasota, Siesta Key Fishing Charters serves the greater Siesta Key area and offers up customized tours for new anglers and experienced guests alike. You’ll hop on board quality vessels that are already stocked up with the gear you’ll need for an amazing day on the waves. The waters that surround this area are home to everything from yellowtail and porgys to grouper depending on what you’re hoping to reel in. For those interested in balancing out their angling experience with sightseeing, Siesta Key Fishing Charters also offers dolphin spotting tours.

Siesta Key Bike and Kayak LLC

While time spent sunbathing on the beach and exploring the waves are both exciting for visitors to Siesta Key, this is a destination that’s often best enjoyed on two wheels! When you can’t wait to discover new landmarks at your own pace, the professionals at Siesta Key Bike & Kayak LLC are happy to help get you paired up with just the right bike rental to make the most of a day on the sandy trails. Located off Old Stickney Point Road in Sarasota, Siesta Key Bike and Kayak LLC is a one-stop-shop for all things Siesta Key cycling. This company offers up traditional bike rentals as well as electric bike options upon request. Looking for even more? Siesta Key Bike and Kayak LLC provides rental options for kayaks, stand up paddleboards, and scooters if you’re hoping to take things at a faster clip. Kayak eco-tours are also readily available upon request for those guests looking pair time on the trails with time exploring mangrove tunnels alongside a knowledgeable and friendly guide.

Book a Trip in Winter in Siesta Key Today!

No matter what season you plan your trip to Siesta Key, the team at Rent Siesta Key is happy to help take care of all of your accommodation needs. Be sure to reach out today to learn more about our many vacation rental properties in the area and to begin planning your next sunny, Florida adventure!

Florida’s year-round sun and warmth is what makes it the ideal getaway no matter what time of year you’re looking to visit. With air temperatures in the mid-50s to mid-70s and water temps from the high 50s to mid-60s, some may want a little extra warm up. There are several Siesta Key restaurants that can help with hot food for any meal.

Daiquiri Deck

Known for frozen daiquiris in a wide range of flavors, they also have plenty of tasty dishes to keep you warm on your winter break. For a taste of the sea, try the sea shrimp & scallop skewers – two skewers loaded with jumbo Gulf Shrimp and sea scallops, then grilled and served over rice with Cajun or Jerk seasoning. Take an adventure in eating and order the seafood mac & cheese – lobster, shrimp, and crab tossed in a white cheddar cheese sauce mixed with white wine sauce, macaroni pasta, and topped with bread crumbs. Land lovers will enjoy stuffed skirt steak – a tender and juicy roasted skirt steak stuffed with fresh spinach and smoke gouda and served with roasted potatoes and asparagus. For some handheld warmth, try the sirloin steak sandwich – a six-ounce sirloin cooked to order and crowned with caramelized onions and mozzarella cheese on ciabatta bread, or grab a short rib grilled cheese – slow-braised short ribs prepared Jamaican style, topped with smoked gouda, and served on toasted white break with a side of orange marmalade. Carry-out, dine-in, and delivery options available and operating for their regular full-service schedule of 11 a.m. to midnight.

Toasted Mango Cafe

Warm up and fuel up for the day ahead with a warm breakfast at Toasted Mango Cafe. Enjoy favorites like eggs Benedict – served in a variety of styles from veggie (black bean veggie with avocado), traditional, or smoked salmon. Go for a Gulfside omelet with seasoned Bluefin crabmeat, Gulf shrimp, spinach, tomato, and Jack cheese, or the Farmhouse omelet with fresh kale, sweet corn, zesty breakfast sausage and pepper jack cheese. Choose from a range of waffles from Belgian, fruit-topped, or the house special: a Belgian waffle topped with fresh mango, toasted coconut, and real whipped cream. Stick to the traditional with French toast or tickle your taste buds with apple walnut pancakes or banana granola pancakes. Dine-in or carry-out is available.

City Pizza Bar & Grill

Whether it’s pizza or pasta, Italian food often fills and warms all at once. On Siesta Key, find pizza and other traditional Italian fare at City Pizza Bar & Grill. For a taste of the seaside, enjoy mussels marinara with spaghetti, or deep sea calamari with your choice of pastas. Warm up with Italian classics like lasagna, meat or cheese ravioli, or baked ziti. For something other than pasta, try a calzone, a hot sub like the meatball parmigiana, or their half-pound hamburger. If you came for the pie, choose from standard toppings like Italian sausage, green peppers, or pineapple. Try something a little different and add a specialty topping like clams, shrimp, or eggplant, or try a specialty pizza like the Black Pearl Seafood Pizza (shrimp, clams, spinach, tomatoes, black olives) or the White Pizza – a blend of ricotta, mozzarella, and provolone cheeses with no sauce. Delivery, dine-in, or carry-out options are available.

Pride of the South BBQ

Take a quick jaunt to Sarasota for the mouth-watering, soul-warming, BBQ flavors served up at Pride of the South BBQ. All of their meats are smoked fresh daily and smothered in your choice of their specialty barbecue sauces. Choose a pulled pork, smoked turkey, brisket, or meatloaf sandwich. Lick the sauce off your fingers after a half-slab or full-slab of spare ribs, or a half-rack or full-rack of baby back ribs. Poultry lovers will enjoy a full pound of turkey or a whole or half chicken. Their BBQ meatloaf comes in three sizes – ¼, ½, or full pound. Make any of these meats into a “plate” by adding your choice of two side dishes. The kids won’t go hungry either, with a kid-size pulled pork sandwich or chicken tenders accompanied by a side and drink. The whole menu is available for dine-in, carry-out, or delivery.

Hot Winter Meals on Siesta Key

The area is dotted with places to grab a hot winter meal when you don’t want to cook on vacation. If you’re a home chef who can’t resist the temptation to cook, even on vacation, a vacation rental by Rent Siesta Key is the place for you. You’ll enjoy the comforts of home, like a fully equipped kitchen ready to handle your next culinary masterpiece, in-unit washer/dryers, large bedrooms and living spaces to sprawl out and relax, and private outdoor spaces like patios or balconies. We have one-bedrooms for a more intimate experience for you and your small group, all the way up to six-bedroom units to accommodate your family or group reunion.

Choose a premium unit for upgrades like stainless steel high-end appliances, flat screen TVs, hardwood floors and more. Ask us about select rentals that allow your furry friend to have the vacation of a lifetime too.

Contact us today to book your stay where you’ll make memories to last until you come back and beyond!

Every year comes with its share of ups and downs, but it’s fair to say that 2020 has left people the world-over longing for a change. The many stresses and worries of the past 12 months have undeniably left fatigue in their wake, often paired with a need to get out of homes and back out into the world in some capacity. With New Year’s just around the corner, it’s highly likely that everyone is looking forward to leaving the past year behind and looking forward with hope to something new. When part of what’s keeping you down is your familiar accommodations, maybe a trip somewhere sunny and welcoming is just what you need to get that new 2021 perspective firmly in place, like a vacation on Siesta Key New Years Eve. When you’re a traveler who can’t wait to explore once again, New Year’s is the time to do it and Siesta Key is the ultimate destination.

An Ideal Siesta Key New Years Eve Getaway

As scenic as it is welcoming, Siesta Key is a beautiful barrier island situated in the Gulf of Mexico that’s within proximity to Sarasota. This alluring locale is loved by travelers from near and far for its chalk-white beaches, emerald waves, and plenty of options for fun. In the year 2021, it will be more important than ever before to find vacation destinations where social distancing can be practiced, but loved ones remain close. There’s no better time to put this travel philosophy into place than over New Year’s this year and while you’re here, consider adding the following fun activities to your itinerary too!

Explore Siesta Key Village

If you’re a traveler that finds their getaway vibe most easily when surrounded by vibrant shops, exciting storefronts, and a variety of savor restaurants, bars, and cafes, then beginning your New Year’s holiday in Siesta Key Village is bound to inspire. Siesta Key Village is brimming over with options for fun but comes with the added benefit of being only a couple of city blocks in total, making it a comprehensive place to explore without being overwhelming. The area is home to just over 100 stores, shops, and points of interest and is known for its dynamic nightlife scene when the sun goes down.

Spend Time at Turtle Beach

The southern end of Siesta Key is home to Turtle Beach—an iconic toes-in-the-sand stop for those that plan on creating a stay that revolves around time under the sun! Turtle Beach is a great choice to add to your New Year’s getaway itinerary when you’re looking to get out on the water as it hosts plenty of convenient boat ramps to use. It’s also a scenic destination where a picnic lunch can be enjoyed with family and friends. Pack up your favorites savory items and settle into a seaside picnic table for a one of a kind fresh-air Florida meal. Much like the name indicates, Turtle Beach is also a fun destination for those with a heart for wildlife. It’s a great place to see sea turtles throughout the year.

Soak Up the Sun at Crescent Beach

If you’re truly dedicated to sunbathing your way through the New Year’s holiday, then Crescent Beach should be on your list of must-visit destinations. This is an ideal locale for those that can’t wait to settle into their lounger and watch the waves roll in with coastal style. Whether you’re headed this way with family or friends, the waters that lap the shoreline of Crescent Beach make for an inviting place to follow up time under the sun with a swim. For those that are more inclined to seek out sensational natural landmarks during their holiday visit, Crescent Beach also works as an access point to the iconic Point of Rocks. This area is made up of one of a kind limestone outcroppings. Collectively, the stones create a natural surrounding for coral reefs and tidal pools that are sure to fascinate. If you happen to be a photographer, this destination is particularly appealing on film!

Book an Adventure with Siesta Key Watersports

When you’re hoping to pick up the pace this New Year’s, partnering with the team at Siesta Key Watersports will help you accomplish exactly that. This premier provider of all things outdoor fun can help visitors book everything from parasailing adventure to waterskiing journeys. For guided experiences, make the most of their dolphin-spotting cruises while renting a jet ski for the day is bound to be a delight as well!

Book Today

There’s no reason to wait when you’re ready to enjoy the fun of a Siesta Key getaway over New Year’s. When your travel plans bring you this way, the team at Rent Siesta Key is ready to help you find just the right accommodations to match your exciting getaway experience! Reach out today to learn more about our many properties and to begin planning.

Sarasota Oktoberfest

October 16-18, 2020

JD Hamel Park at Gulfstream and Main Street, Sarasota, FL
Friday 4pm-10pm, Saturday 11am-10pm and Sunday 11am-6pm
Free Admission

Join us for the 3rd Annual Sarasota Oktoberfest in beautiful downtown Sarasota in JD Hamel Park at Gulfstream and Main Street, brought to you by Paragon Festivals, with the Sarasota Downtown Merchants Association and their special guest the Humane Society of Sarasota County. You will be able to stuff yourself with smoked sausages, roasted meats, sauerkraut, cabbage, and pretzels while enjoying authentic German music and dancers and live music performances in rock, soul, big band, R&B and more!

Between performances shop the Marketplace of arts, crafts and select fine products and services.

The Humane Society will have their “Big Mac” mobile adoption center onsite. Please take a few moments to stop by and say “Hi” to the dedicated staff and meet their extended family of friends awaiting adoption. Find a new companion and lend support to a wonderful and compassionate organization.

Map, Directions & Parking

Driving Directions

GPS Address: JD Hamel Park, Gulfstream & Main Street, Sarasota, FL

1) from St. Armands Circle: take John Ringling Blvd (SR-789) across Rt. 41 to the intersection of Cocoanut and Gulfstream (~4 minutes / 2.33 miles). The Oktoberfest festival is in JD Hamel Park, directly ahead of you starting at Main Street and proceeding south.

2) from North or South of downtown Sarasota: take Rt. 41 towards Marina Plaza/Main Street. Turn east on Main Street and continue on Main Street to Gulfstream. The Oktoberfest festival is in JD Hamel Park on your right.

Parking Information

The Palm Avenue Garage (1289 Palm Avenue)

Garage parking is available at the award-winning Palm Avenue Garage, located one block from Main Street on North Palm Avenue, only steps away from Five Points intersection in downtown Sarasota. The Palm Avenue Garage is a newly designed and LEED Certified facility utilizing the latest technology in equipment and design. The garage has spaces for 729 vehicles with handicap parking located on each floor close to the elevators. The city provides four reserved electric car-charging stations on the ground floor. The Palm Avenue parking garage is a perfect location to park short or long-term visits to downtown Sarasota.

State Street Garage (1538 State Street)

The parking garage bi-lateral entrance and exit points will provide excellent access from both State Street and Ringling Blvd. Parking spaces are located on levels 2 through 6, with motorcycle, bicycle and handicap van access on the ground floor. With downtown parking demands so high, parking time limits will ensure there is always a parking space available in either the 2-hour parking “shopper zone”, or the 4-hour time restricted area on levels 4 through 6.

2nd Street Garage (1400 Block of 2nd Street)

The 2nd Street Garage is located between First and Second streets, directly across from Whole Foods. Ground floor parking is intended for customers of Whole Foods, while the second and third levels of the garage are open to the public (except where posted). The public parking access ramp is located on Second Street, near the corner of Central Avenue. There are time restrictions in the facility that are monitored by the City Parking Division and for which citations are issued for time violations. The time restrictions are as follows:

Ground level: 2 hours Levels 2 and 3: 4 hours

 

(Click Here For More Information)