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Are you excited about your upcoming vacation in Siesta Key? Located on the southwest coast of Florida, this gorgeous family-friendly location is blessed with lots of natural beauty. Think of long stretches of white sand in front of the vast blue ocean. The waves, water, and sand create a breathtaking landscape where you can have a great time with your loved ones. Even if you choose to simply sit on the shore and admire the waves, you would feel extremely happy on a successful vacation. From plenty of gourmet restaurants to casual food joints, bars serving delicious cocktails to cafes with fresh coffee, this place has it all. You can find many activities in Siesta Key including family-friendly indoor and outdoor attractions for a fun experience. Get ready for lots of nature trips as Siesta Keys and surrounding areas have plenty of state parks and nature conservation areas.

When you plan a trip to Siesta Keys, you can find options for activities like fishing, camping, water sports, swimming, kayaking, paddle boating, snorkeling, scuba diving, sailing, and so much more. Many budget-friendly activities are still fun while traveling with your family. The vast outdoors is ready to welcome you for a relaxing trip. Spend time on the shore where you can enjoy picnics, fun games, and so much more with your loved ones.

Browse Our Siesta Key Villa Rentals Here!

Family-Friendly Activities for a Memorable Vacation

While traveling with a group, you would need to check out activities appropriate for all age groups. You would not come across any challenges in Siesta Keys as it has plenty of options. There is something unique, interesting, and engaging for both kids and adults so you can enjoy the experience to the fullest. If you enjoy hiking, you can head to many nature preserves where you also get an opportunity to admire the native flora and fauna.

You can visit the popular Siesta Beach which has a beach-facing park and lots of play areas. It is ideal while spending time with family where you can enjoy activities like kayaking, swimming, surfing, jet skiing, snorkeling, and much more. Kids can have a great time on the shore making sandcastles and fun sand structures. Head to the gorgeous Crescent Beach where you capture the gorgeous sunset. It is popular for long stretches of white sand and gorgeous ocean. For a quieter and more relaxing experience, you can head to Turtle Beach. As the name suggests, Point of Rocks is a scenic and unique geologic formation with big rocks as the central highlight. Located next to a scenic beach, it is a perfect spot to spend an afternoon admiring the waves. It is also a popular spot where locals and visitors arrive to see the local flora and fauna. You can see lots of birds and wildlife. If you and your group enjoy nature, you must visit the popular Marie Selby Botanical Gardens. Here, you can see a wide range of native, exotic, and unique plants. You can also see bamboo gardens, bonsai, and lots of tropical plants.

Another famous spot where you can enjoy a nature walk is the Myakka River State Park. Spread over a large area covering more than 37,000 acres, this attraction has many native birds and animals. You can enjoy hiking, fishing, kayaking, and boating. We can suggest the happening and popular Siesta Farmers Market where you can shop for a variety of local goods, produce, artifacts, and much more. It is also a great place to learn about the local culture and vibe of the area. The market hosts a wide range of local vendors covering a variety of goods. Many companies offer guided boat tours. You can admire the breathtaking beauty of the ocean while learning more about the area and its special features. One of the best ways to explore the different areas in the city is through biking. You can find many rental shops that offer bikes of varying sizes, colors, and styles. You can rent a bike and roam around the area while checking out different parks, shops, restaurants, and other attractions.

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Rent the Right Accommodation for Your Stay

If you are excited to book your next trip to Siesta Key, you can check the excellent options of vacation rentals with us at Rent Siesta Key. From cozy condos for a romantic getaway to spacious beachfront houses with multiple rooms, we can offer it all. Stay at a luxurious, comfortable, and beautiful accommodation that can make you feel at home. Our fully furnished rentals have a wide range of convenient amenities including internet access, in-unit washer and dryer, central air-conditioning, parking, community amenities, and much more. The open-floor concept of the house can offer both private and common areas where you can have a great time with your folks. The vacation rentals may offer a swimming pool, hot tub, gas grill, and chairs in the outdoor area. Expect comfortable bedrooms with exceptional furnishing, modern décor, electronic appliances, full baths, cabinets, and much more. You can find rentals with a fully equipped kitchen so you can cook a quick breakfast or lunch before heading out for the day. The kitchen includes everything from cookware to utensils, appliances to cabinets, and other essential resources. Some of the appliances include a cooking range, oven, microwave, dishwasher, and refrigerator.

Book Your Siesta Key Vacation Home Here!

Get in touch with the team at Rent Siesta Key to book your accommodation with us. Our team can suggest the right choices based on your preferences and interests during your stay.

Fun, sun, sand, and warm temperatures year-round make Florida one of the best spots for a getaway any time of the year. If you’re looking for all that along with a bit of fall flair, you’ll find everything you’re looking for in Siesta Key this fall season. There are plenty of fall activities, festivals, and fun things to do in Siesta Key to keep you happy, busy, and in a crisp, fall mood throughout your stay.

Browse Our Siesta Key Rentals on the Beach Here!

Beaches

Whether it’s the beat of the sun on a hot summer day or a crisp fall day, your island vacation won’t be complete without a visit – or two or more – to the beach. Pack your beach gear and make the short trip to the beach for some much-needed beach time and R&R. While swimming in the shimmering waves of the Gulf might not be on the list, you can still sit out in the sun and enjoy the weather by sunbathing or reading a book. Take a walk or run on the beach for some exercise or brave the cooler water for adrenaline-pumping activities like jet skiing, or parasailing.

Oktoberfest

When summer turns to fall, many locales across the country celebrate their own version of Oktoberfest. The festival, which started in Germany, spread around the globe and now people everywhere get together to share beer, music, games, festivals, and more. The island may celebrate a little differently from the mainland, but there are nearby mainland locales that may offer a bigger party.

Sand Sculpting Festival

There can’t be anything more appropriate to celebrate on an island than sand sculpting. The International Sand Sculpting Festival takes place every November in Siesta Key. These are not your average sandcastle built with a pail and a bucket at the water’s edge. From large, intricate castles with carved details including windows and doors to life-size replicas of famous people, sculptors go all-out to showcase their skills and talent. You can buy tickets for the event on their website. Afterward, try your hand at building your own sand sculpture.

Check Out Our Siesta Key Villa Rentals Here!

Hiking

Stroll the streets of Siesta Key or hike its beautiful many trails. Fall is one of the best times, as the weather is cooling down but still warm enough to keep you comfortable. Explore everywhere your feet can take you that your rental car can’t. Pack your essentials – like water, sun gear, and whatever else you need, and set out on an adventure. Make sure one of those essentials is your camera, as you’re bound to spot some of the island’s wildlife while you’re out.

Bicycle Rentals

Keep the rental car parked at your accommodations and gather your loved ones for some exercise. Explore the many walking and biking trails leading to all the nooks and crannies of Siesta Key where your motor vehicle just can’t go. Bike rental companies offer an array of options, from cruisers or mountain bikes, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Ask about locks, extra baskets, other accessories, and safety gear like lights and helmets. There may even be perks like delivery to your accommodations.

Trolley

After you’ve walked, hiked, or biked your way around the island, hop on the free trolley for a different type of wheeled transportation. Save the gas in your rental car for an off-island trip and conserve your own energy for the fun you’ll have at your destination when you take the Siesta Breeze Trolley to just about any destination on the island. Experience the fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between. Get on or off at any stop and spend as long as you like at the location before meeting the trolley at another stop or when it comes back your way.

Fall Fun in Florida

When you book a fall getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with loved ones. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group. If you don’t want to go out to eat, make a group 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. Opt for a premium unit that may include perks like a fireplace, double ovens, stainless steel appliances, flat-screen TVs, a private pool – some even screened in for added protection from the Florida sun and more. Include everyone by asking about select rentals that allow your fur babies to stay.

Book Your Siesta Key Vacation Home Here!

Contact us today to book your fall Florida getaway in Siesta Key!

The warmth and sun of Florida are a major attraction any time of year. Anticipate the cooling weather and return of fall and spend a little extra time in the sun and warmth with a trip to the Sunshine State’s 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 while you cherish the last days of summer on your Siesta Key Labor Day weekend.

Browse Our Siesta Key Villa Rentals Here!

Beach Time

An island vacation, no matter what time of year you’re here, without a visit to its beaches is virtually unheard of. You and your loved ones are only moments away from the luscious sand and vibrant waters of the Gulf of Mexico no matter where you are on the island. Fill the cooler, pack the beach gear, and stake your territory with blankets and umbrellas as you prepare for a day of lounging on the shore, or a dip in the Gulf.

Snorkeling

Snorkeling is a great way to get in the water and explore the area, especially on the islands. Whether you rent gear from a local shop and explore on your own or book a charter tour, it’s a magical way to see the underwater world that surrounds Siesta Key this Labor Day. 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 and somewhat shallow area. If you’re looking for a group vibe, charter a boat with Key Life Charters where you can bring your own snacks, including adult beverages. Expand your snorkeling adventure by adding experiences like sightseeing, dolphin and wildlife spotting, and more for your unique and perfect trip.

Parasailing

Sail high over the water and gain a whole new perspective on where you’ve chosen to spend your Labor Day getaway 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 – 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 and coming down safely on the deck. Bring your waterproof or disposable camera to capture the memories from your perspective in the harness. 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 whenever you like. Rides are approximately 15 minutes of airtime, but the whole excursion duration depends on the number of fliers.

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Private Cruise

There are plenty of boat charter companies that offer cruises. Stay out of the cooling waters of the Gulf while still enjoying marine activity. Watch the sunset, search for dolphins and other marine life like manatees and aquatic birds, or just sit back and relax as the captain steers through the sea. Sip on an adult or other beverage as you take in the beautiful Florida coast and Gulf waters with your loved ones for a great way to end any day of your stay. Daytime and sunset cruises are available.

Bicycle Rentals

Siesta Key has a land area of just 2.4 miles, so there are bound to be places to explore where your rental car just can’t reach. Instead of trying to see everything by car, get some exercise by exploring the many walking and biking trails that bring you closer to the sights inaccessible by car. Choose from 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 choose to take a romantic ride on a bicycle-built-for-two – there’s a bike to fit the needs of everyone in your group! Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.

Labor Day Fun 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 you’re here. Rent Siesta Key has a rental to fit your needs, from one-bedroom units all the way up to six bedrooms for a Labor Day reunion with friends or family. 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 together. 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.

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

The year-round Florida sun and warmth make it an ideal destination any time of year, but add the red, white, and blue, of the 4th of July and you can prepare for even more fun. Gather your loved ones and pack your bags with your most patriotic possessions for a fun and exciting vacation and an island-style 4th of July. Then set your sights on the keys and the many fun and unique offerings you’ll find there that will have you building a vacation that keeps everyone happy and busy and provides memories to last a lifetime.

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Siesta Key Fireworks

Celebrate the 4th with fun and fireworks. The show is located off the shores of Siesta Beach, just north of the volleyball courts, but there are plenty of other great vantage points like Crescent Beach, the Public Beach, or you can even board a vessel and head out into the waters of the Gulf of Mexico or the Intracoastal Waterway. The free, family-friendly show takes place July 4th at dusk. Pets and personal fireworks should be left at home.

Beaches

While you’ll have to wait until the sun goes down to enjoy a fireworks display, the beaches of Siesta Key are open all day. Pack your beach gear and stake your claim on the beach for a day of sun, sand, and fun every day of your trip. Gather your group, your beach chairs, and sand toys and head to the Siesta Key Beach July 4th for a swim in the Gulf, or just to work on your tan. To make the day more festive, wear your red, white, and blue, pack a picnic lunch, and celebrate independence, island-style.

Island Hopping

Siesta Key’s size – it’s only 2.4 square miles of land – means there’s not a lot of room for a large-scale 4th of July event. You can get your fill of patriotic events when you do a little island hopping. Longboat Key, Bradenton Beach, and Anna Maria Island are all hosting large 4th of July events, many of which include parades, fireworks, cookouts, and plenty of patriotic fun. The Sarasota P1 Offshore Boat Races take place off of the shores of Lido Key July 1st – 3rd. Mainland Sarasota is also going all-out for the holiday.

View Our Siesta Key Rentals On the Beach Here!

Trolley

Hop on the trolley, which may be showing its best red, white, and blue décor, for a visit to the many businesses and sites along its route. Save the gas in your rental car for an off-island trip, conserve your own energy and spare the bike ride or walk between destinations for the fun you’ll have at your destination when you take the Siesta Breeze Trolley. Check out boutiques, shops, and restaurants. Many will be decorated in red, white, and blue for the patriotic holiday, and some even offer special events, discounts, and menus to mark the country’s independence. Experience fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between.

Other Activities

There are plenty of activities to keep you busy on your island respite this 4th of July. Many businesses will be decked out in red, white, and blue, and may even be offering special patriotic-themed services. Take a cruise through the water surrounding Siesta Key and try to spot dolphins, manatees, rays, and more. Keep the water activities going with SCUBA diving and snorkeling, paddleboarding, kayaking, or just going for a swim in the waves with loved ones. Florida is known for its world-class fishing, so get yourself a Florida fishing license and head out on an adventure. Take to the skies with a parasailing experience, stick to shore with an electric bike tour, or pamper yourself with a massage or facial at a spa.

Fourth of July Fun in the Florida Keys

When you book your 4th of July getaway with Rent Siesta Key, you won’t be short on fun and patriotic activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind in a private home after a fun-filled day. Enjoy a one-bedroom for your small family, all the way up to six bedrooms for a larger group red, white, and blue reunion. For more privacy, choose a single-family home with a garage. Make a group meal in your unit’s fully equipped kitchen, many including stainless steel, and 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 group for a TV show or movie. Opt for a premium unit which may include perks like a fireplace, double ovens, flat-screen TVs, or a private pool. Include everyone by asking about select rentals that allow your fur babies to stay.

Contact us today to book your 4th of July getaway to Siesta Key!

Book Our Siesta Key Vacation Homes Here!

The year-round sun and warmth of Florida makes it an ideal destination any time of year. No matter where you choose to go in the Sunshine State, there is plenty to see and do. Choose the sunny, sandy shores of the keys adds another layer of rest and relaxation to your Florida vacation. This summer, take an island vacation. To make sure everything goes as planned for your summer 2022 island retreat, you’ll want to start planning well in advance. Starting now means you’ll have your pick of everything that will make your vacation great, including reservations, rentals, activities, and most importantly: where you’ll stay.

Discounts

Experienced travelers know that booking travel necessities like airfare, accommodations, and admission to popular attractions secures you some of the best of the best items at the lowest price. Last-minute bookings often come with a premium, as well as missing out on the rental property that’s right for you, while those who plan in advance can take advantage of lower prices on the most sought-after homes on Siesta Key. Lower costs may apply to other aspects of your trip. Airfare, vehicle rentals, attraction admission, and popular activities offer discounts to travelers who think ahead and book now.

Priority

First come, first served is a saying popular with businesses that want to attract more customers. Arriving early often comes with perks like guaranteed admission, lower entry fees, and other special treatment only available for a limited time. The same can be true for vacation rentals. Booking your 2022 summer, Siesta Key getaway with Rent Siesta Key now means you’ll have your choice of vacation rental homes so you can reserve the one that will enhance your island experience however you like.

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Peace of Mind

Booking your 2022 summer vacation now and securing reservations for your preferred vacation home on Siesta Key means you don’t have to worry about a major part of your trip as the days go by. Once you’ve secured the vacation home of your dreams, you can focus on booking the other activities and attractions that will make your summer 2022 island adventure one to remember for years to come.

Organization

Booking your vacation rental with Rent Siesta Key for your 2022 summer getaway not only means you can focus on other trip planning to-dos, but it also means you have more time to prepare every last detail. If you’ve never been to Siesta Key, use the extra time and peace of mind to download maps of the area around your rental as well as the best routes to all the fun places on your must-do list during your trip. Gather the things you’ll need for your trip of a lifetime and store them somewhere easily accessible so all you’ll have to do is pack the car and head to the airport.

Time to Save

With everything booked, down payments secured, and everything else for your perfect summer vacation on Siesta Key in place, you’ll have plenty of time to save extra spending cash. Save your change from regular purchases in a jar or move money each week to an account opened especially for vacation expenses. There are bound to be impromptu adventures that require admission fees, groceries during your stay, other items not provided at your vacation rental, other incidentals, as well as some fun souvenirs to bring home.

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Rentals

Travelers who book early not only have secured exactly what they want, they may end up getting a little more. Rather than having to rent, or even purchase items you won’t be taking home with you – bikes, beach equipment or sand toys, and items not traditionally offered to renters may be included in your fees at no extra charge.

Get Everyone Prepared

Planning your summer 2022 trip to Siesta Key well in advance means there’s plenty of time to get everyone prepared for the journey. New bathing suits or summer clothes, luggage, and other large purchases can be made. You can create personalized lists of the items needed for the duration of the trip can be figured out and purchased or packed in advance rather than being tossed in carelessly at the last minute. You’ll also have plenty of time to secure the valuables you’re not taking with you.

Book Early for 2022 Summer Siesta Key Fun

When you book your summer 2022 getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with your group. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group. Prepare a meal in the fully equipped kitchen and enjoy it 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. Opt for a premium unit for perks like double ovens, stainless steel appliances, flat screen TVs, a private pool, and more. Include everyone this summer by asking about select rentals that allow your fur babies to stay.

Contact us today to book your summer 2022 getaway in Siesta Key!

Find The Perfect Summer Villa In Siesta Key

Fun, sun, sand, and warm temperatures year-round make Florida one of the best spots for a getaway any time of year. If you’re looking for all that along with a bit of fall flair, you’ll find everything you’re looking for at Siesta Key this fall season. There are plenty of fall fun and festivals to keep you happy, busy, and in a crisp, fall mood throughout your stay. Check out some of the best fall activities in Siesta Key:

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Sand Sculpting Festival

There can’t be anything more appropriate to celebrate on an island than sand sculpting. Each November, Siesta Key hosts the International Sand Sculpting Festival. These are not your average sand castle built with a pail and a bucket at the water’s edge. From large, intricate castles with carved details like windows and doors to life-size replicas of famous people, the sculptors go all-out to showcase their skills and talent. You can buy tickets for the event on their website.

Beaches

Whether it’s the beat of the sun on a hot summer day, or a crisp fall day, your island vacation won’t be complete without a visit – or two – to the beach. Pack your beach gear and make the short trip to the beach for some much-needed R&R. While swimming in the shimmering waves of the Gulf might not be on the list, you can still sit out in the sun and enjoy the weather. You might try your hand at building your own sand castle like one you saw at the festival.

Oktoberfest

When summer turns to fall, many locals across the country celebrate their own version of Oktoberfest. The festival with German roots spread around the world and now people everywhere get together to share beer, music, games, festivals, and more. The island may celebrate a little differently from the mainland, but there are nearby mainland locales that may offer a bigger party.

Bicycle Rentals

Keep the rental car parked at your accommodations and gather the group for some exercise and a different way to explore Siesta Key. There are many walking and biking trails that take you to all the nooks and crannies of Siesta Key where your motor vehicle just can’t go. Many rental companies offer an array of options, from single-seat bikes with or without gears, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Make sure to ask about locks, extra baskets, other accessories and safety gear like lights and helmets. There may even be perks like delivery to your accommodations.

Check Out Our 1-Bedroom Rentals Here!

Hiking

Stroll the streets of Siesta Key or hike its beautiful trails. Fall is one of the best times, as the weather is cooling down but still warm enough to keep you comfortable. Explore everywhere your feet can take you that your rental car can’t. Pack your essentials – like water, sun gear, and whatever else you need, and set out on an adventure. Make sure one of those essentials is your camera, as you’re bound to spot some of the island’s wildlife while you’re out.

Trolley

After you’ve walked, hiked, or biked your way around Siesta Key, hop on the free trolley for a different type of transportation on wheels. Save the gas in your rental car for an off-island trip and conserve your own energy for the fun you’ll have at your destination when you take the Siesta Breeze Trolley to just about any destination on the island. Experience the fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between. Get on or off at any stop and spend as long as you like at the location before meeting the trolley at another stop or when it comes back your way.

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Fun Fall Activities in Siesta Key, Florida

When you book a fall getaway with Rent Siesta Key, you won’t be short on fun activities in Siesta Key to fill your time while you’re here. From spending time celebrating the season at your rental to celebrating with visitors and locals alike at a festival, you’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with your group. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group or reunion. For more privacy, choose a single-family home with garage. If you don’t want to go out, make a group 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 gather the group for a TV show or movie. Opt for a premium unit which may include perks like a fireplace, double ovens, stainless steel appliances, flat screen TVs, private pool – some even screened in for added protection from the Florida sun. Include everyone by asking about select rentals that allow your fur babies to stay.

Contact us today to book your fall Florida getaway in Siesta Key!

The warmth and sun of Florida is an attraction any time of year. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities the area has to offer. While the weather may be perfect for the majority of your trip, you’ll want to prepare some activities for times when the weather doesn’t cooperate with your beach and outdoor schedule. There are many “rainy day” activities in Siesta Key to enjoy and pass the time when the weather is gloomy.

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Siesta Key Village Shops

Touring a town is a great way to get to know its nooks and crannies as well as the locals. When the sun isn’t shining, that doesn’t mean that the exploration needs to stop, just take it indoors! The charming shops and restaurants found in Siesta Key Village will give you hours of fun, browsing, window shopping, and delicious food to keep your mind off of the pitter-patter of rain outside. You’ll score some great island-themed décor, clothing, and accessories to put on display once you get home and turn your home into an island getaway.

Siesta Key Wine Bar

An activity made especially for the adults of the group is a visit to Siesta Key Wine Bar. The self-billed “home for wine lovers,” the establishment at the north end of Siesta Key Village includes a tasting bar and sitting areas for you to enjoy a glass of terrific wine. The wine bar features local Florida wines, as well as reds, whites, and “bubbles” from across the globe. Visit the wine shop to take home your favorites or arrange to have your favorites shipped to your home. Keep in mind there is limited ability to ship to certain locales and yours may not be available.

Spa Day

While your outdoor relaxation plans may be canceled, that doesn’t mean the relaxation can’t take place indoors. Book yourself some time for rest, relaxation, and rejuvenation at a local spa. Choose from treatments like a mani/pedi, massage, body wrap, facial, and more. Staff will help you create a package just for you so you can fully relax your mind, body, and spirit. Some establishments may offer salon services, so you can get a new cut or style to go with your relaxed mood. Ask about treatments designed especially for the men of the group who need a recharge.

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Relaxing Rental

You don’t need to go out on the town for a good time, indoors or out, rain or shine. You can always choose to relax around your Rent Siesta Key vacation rental home. Many rentals include books, a movie library, board games, puzzles, and other indoor activities to keep you busy. Staying right where you are can be just as engaging as a day out touring the town. If you have any personal favorite games from home, make sure they make the packing list so you can enjoy those, too, if the mood strikes.

Dining

Lift your spirits as the rain falls with a meal out on the town. There are many restaurants on Siesta Key that will satisfy any hunger or thirst you may have. From a casual lunch or dinner to a special date or celebration, you’ll find something delicious to fit the mood.

Sarasota

If the rain insists on lasting another day, or you’ve worn out all the things to do on-island, take a trip to the mainland for some fun. Sarasota is full of fun, with activities like museums, escape rooms, and aquariums, you’ll find something to do to battle the gloom and continue to enjoy your Florida getaway, no matter what the weather is like.

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Rainy Day Fun Activities in Siesta Key

When you book your fun-filled getaway to Siesta Key, you won’t be short on activities to fill every minute of every day, even when the sun isn’t shining. With plenty of activities in Siesta Key to choose from, you’ll find something to do to keep the entire group entertained and happy without the sun. Spend some time in your accommodations if you don’t feel like going out. From a one-bedroom for your small family or a getaway with your sweetheart, all the way up to six bedrooms for a family or group reunion with everyone, you’ll find something by Rent Siesta Key to fit your vacation needs and style.

Instead of getting wet when heading out to eat, stay warm and dry and prepare a delicious home-cooked meal in your rental’s fully equipped kitchen. Recharge with a nap or a good night’s sleep in a private bedroom or spread out in the spacious living area to read a book or watch a movie. Indulge yourself in a premium unit for perks and upgrades like stainless steel appliances, double ovens, flat-screen TVs and much more.

Contact us now to book your stay full of all-weather memories!

The warmth and sun of Florida is a major attraction any time of year. Lounging in the sun or splashing around in the water of the Gulf of Mexico is a fun and relaxing way to while away the time on a Florida getaway, but you’ll want to make sure to experience some of the Siesta Key tours and activities the area has to offer. 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.

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Trolley

If you’re unsure of where to start with the Siesta Key tours and experiencing everything Siesta Key has to offer, hop on the trolley. Save the gas in your rental car for an off-island trip and conserve your own energy for the fun you’ll have at your chosen destination when you take the Siesta Breeze Trolley. Experience fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between. Hop on and off as you spot a new place to go explore.

Dolphin Cruise

Head down 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 thrill- and adventure-seekers. 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 these majestic mammals. You’ll see more than dolphins! Keep your eyes open and your camera ready to capture glimpses of manatees, rays, and even whales at certain times of year. Any of these beautiful sea creatures might even come near the boat to swim alongside!

Parasailing

Gain a whole new perspective on where you’ve chosen to spend your time of relaxation 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 of Mexico. 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. You can choose to 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 in-flight perspective. Parasail Siesta takes several professional digital camera pictures of your flight from the boat’s perspective 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.

Sunset Electric Bike Tour

Renting a beach cruiser or mountain bike from a bicycle rental company on the island is a great way to get around and add a little daily exercise to your vacation plans. Take a sunset ride to wind down for the evening. For a unique experience, trade that ‘regular’ bicycle for an electric bike! Endless Summer Eco Tours and Rentals offers a sunset electric bike tour of Siesta Key. The bikes have five-level pedal assist and on-demand throttle so you can give yourself as much or as little of a workout as you want as you ride along the shores of Siesta Key past Siesta Beach and Siesta Key Village to Patriot’s Point. Stop and view the flag-lowering ceremony conducted nightly by a local resident. Call out the name of a loved one in the armed forces and hear a bugle rendition of taps. After the ceremony, turn around and head back to the starting point. Book a private tour for your group or join others for a small-group public tour. All skill levels are welcome.

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Experiences on Siesta Key Tours

When you book your fun- and tour-filled getaway to Siesta Key, you won’t be hard-pressed to find something 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 reunion with friends or family.

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The year-round Florida sun and warmth makes it an ideal destination any time of year. Heading there in early summer means getting some of the best of it, so as spring turns toward summer and the heat steadily rises, those looking for a break before the high point of summer vacation season will enjoy an early summer getaway to Siesta Key. Gather your friends and family and pack your bags for a fun and exciting vacation. Then set your sights on the keys and the many fun and unique offerings you’ll find there that will have you building a vacation that keeps everyone happy and busy and provides memories to last a lifetime.

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Paddleboard Lessons

A major part of an island vacation is the sun, sand, and water. Spend some time on the water getting to know a popular water sport. Stand up paddleboarding is an activity the entire group can enjoy. If you’ve never done it before, a lesson with Siesta Key Paddleboards is in order. They offer 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

If your paddleboard lesson didn’t give you enough time in the sun, sand, and water of Siesta Key, a day – or several – at the beach is bound to make up for it. Pack your beach gear and make the short trip to the beach for some much-needed R&R. Swim in the shimmering waves of the Gulf, stretch out to work on your tan, help the kids of the group build sandcastles.

Snorkeling

There are plenty of beach gear rental companies that have the necessities of snorkeling on hand if you want to strike out on your own to explore the underwater world surrounding Siesta Key. A good starting point for your self-guided tour is Point of Rocks, where you’ll find numerous tide pools, moss-covered rocks, and sea life in an easily navigable area that’s only five feet deep. If you’d rather take a tour or trip, Key Life Charters offers an experience like no other. You can even bring your own snacks, including adult beverages. Customize your experience – choose a day of snorkeling, or add on fun like area sightseeing, dolphin and wildlife spotting, and more.

Bicycle Rentals

Park the car at your accommodations and gather the group for some exercise and a different way to explore Siesta Key. There are many walking and biking trails that take you to the nooks and crannies of Siesta Key where your motor vehicle just can’t fit. Many rental companies offer an array of options, from single-seat bikes with or without gears, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Make sure to ask about locks, extra baskets, and safety gear like lights and helmets, and even perks like delivery to your accommodations.

Trolley

After you’ve walked or biked your way during summer in Siesta Key, hop on the trolley for a different type of transportation. Save the gas in your rental car for an off-island trip and conserve your own energy for the fun you’ll have at your destination when you take the Siesta Breeze Trolley. Experience fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between.

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Early Summer in Siesta Key

When you book a getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. From spending the day lounging in the sun at the beach to spending the day lounging in your rental, you’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind in a private rental after a fun-filled day with your group. Enjoy a 1-bedroom for your small family, all the way up to 6 bedrooms for a larger group or reunion. For more privacy, choose a single-family home with garage. If you don’t want to go out, make a group 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 group for a TV show or 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 everyone by asking about select rentals that allow your fur babies to stay.

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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!