Siesta Key vacation rentals

We found 6,754 vacation rentals — enter your dates for availability

Discover a selection of 394 homes, 84 apartments, and other vacation rentals in Siesta Key that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Siesta Key

Showing deals for:Jun 12 - Jun 19

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Find out more about Siesta Key

Why visit Siesta Key

  • Stunning Beaches: Enjoy the soft, white sands of Siesta Beach, known for its breathtaking beauty and crystal-clear waters.
  • Outdoor Adventures: Engage in various activities like kayaking, paddleboarding, and hiking in vibrant urban parks.
  • Charming Siesta Key Village: Explore the local shops, restaurants, and friendly atmosphere of this quaint village.
  • Diverse Accommodations: Choose from spacious vacation homes, cozy condos, or beachfront apartments to suit your needs.
  • Relaxed Vibes: Experience a laid-back atmosphere perfect for families and beach lovers alike.

Popular types of accommodation in Siesta Key

Siesta Key offers a diverse selection of vacation rentals to suit every traveler's needs. Whether you're looking for spacious houses, cozy condos, or beachfront apartments, you'll find the perfect spot to unwind. Our travelers often choose from home rentals, vacation condos, or beach condos, ensuring a memorable stay in this beautiful destination. Explore your options and enjoy a relaxing getaway in Siesta Key.

  • Houses: The top choice for visitors in Siesta Key, offering spacious and comfortable settings for families and groups.
  • Condos: A popular option for those seeking modern amenities and close proximity to the beach.
  • Apartments: Ideal for solo travelers or couples looking for convenient, well-equipped accommodations.
  • Cottages: Charming and cozy, these rentals provide a quaint atmosphere perfect for a relaxing getaway.
  • Villas: Luxurious and spacious, villas are perfect for those seeking upscale living and beautiful surroundings.**

Top attractions in and around Siesta Key

Siesta Key, Florida, is an ideal destination for beach lovers and families seeking outdoor adventures. With stunning attractions like Siesta Beach and the vibrant urban parks nearby, visitors can enjoy a perfect blend of relaxation and city experiences. Whether you're lounging on the soft sands of Siesta Key Beach or exploring the local marina, there's something for everyone to create unforgettable memories on this beautiful island.

  • Siesta Key Beach: Renowned for its powdery white sands and crystal-clear waters, Siesta Key Beach offers a perfect spot for sunbathing, swimming, and beach games. The vibrant atmosphere is complemented by stunning sunsets, making it ideal for relaxation and fun.
  • St. Armands Circle: A charming shopping district with an array of boutiques, restaurants, and art galleries, St. Armands Circle is perfect for leisurely strolls. The city vibes and outdoor dining create a delightful experience for visitors looking to explore local culture.
  • Marina Jack: This bustling marina is a hub for adventure seekers, offering boat rentals, dining, and water activities. With its outdoor vibes, Marina Jack is perfect for enjoying the beautiful waterfront, whether you're sailing or simply relaxing by the water.

Things to do recommended for couples

Planning a romantic getaway in Siesta Key? Indulge in luxury at The Oaks Club or enjoy an elegant afternoon at Sarasota Polo. For a unique experience, try your hand at shooting at Sarasota Trap Skeet and Clays, all within a short drive from the beach.

Things to do recommended for families

Your family will love the soft, white sands of Siesta Beach, perfect for building sandcastles. Explore the vibrant marine life while snorkeling at Point of Rocks, or enjoy a fun-filled day at the Siesta Key Village with its shops and ice cream parlors.

Things to do recommended for groups

Groups visiting Siesta Key can relax on the powdery white sands of Siesta Beach, enjoy a thrilling kayak tour through the mangroves, and savor fresh seafood at local restaurants. Don't miss the stunning sunset at the beach for a perfect end to your day.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Siesta Key

If you're traveling with a group, family, pets, or planning an extended stay, be sure to use the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Siesta Key with young kids: Traveling with young children can be quite a task. It's essential to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siesta Key: For many, a family vacation wouldn’t feel complete without their furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Siesta Key: If you're searching for vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking spot, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Siesta Key

Siesta Key, Florida, is a tropical paradise perfect for beach lovers and families alike. With stunning beachfront access and the charming Siesta Key Village nearby, visitors can enjoy a relaxing atmosphere filled with friendly locals. Explore the beautiful sands of Siesta Beach, indulge in outdoor activities, and soak in the vibrant vibes that make this island destination truly unique. Whether you're seeking adventure or a tranquil getaway, Siesta Key is the ideal spot for your vacation.

  • Sarasota: Located a mere 5 miles from Siesta Key, Sarasota is a vibrant city that offers a delightful blend of beach and urban experiences. Visitors are drawn to its charming downtown area filled with shops, restaurants, and cultural venues. The city boasts beautiful beaches, including Lido Beach and Siesta Key Beach, perfect for family outings. Sarasota is also home to the renowned Ringling Museum of Art, showcasing a rich collection of art and history. With lush parks and a bustling shopping mall center, Sarasota provides a perfect backdrop for family-friendly adventures.
  • Siesta Key Village: Nestled around the area of Siesta Key, Siesta Key Village is a lively neighborhood that captures the essence of a beach town. Known for its laid-back atmosphere, the village features an array of shops, eateries, and entertainment options. Travelers can enjoy recreational areas and easy access to the stunning Siesta Key Beach, famous for its powdery white sands. The village is ideal for families seeking a fun and relaxing day out, with local festivals and events adding to its charm.
  • Lido Key: Just 3 miles from Siesta Key, Lido Key is a picturesque island that offers a blend of relaxation and urban excitement. This destination is perfect for beachgoers and families, featuring beautiful beaches and an urban park for outdoor activities. Visitors can take advantage of shopping centers and recreational areas, making it a great spot to unwind after a day in the sun. Lido Key is also known for its stunning sunsets, providing a perfect end to your beach day.

Best time to go to Siesta Key

If you're planning a trip to Siesta Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January, March and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you eager to cut costs on your upcoming adventure? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to narrow down your options by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. It's rewarding to take the lead in planning. When you join our travel rewards program, One Key, you gain immediate access to exclusive member savings and the opportunity to earn and utilize OneKeyCash on eligible reservations. Enroll today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily organize and view all your travel plans. Any properties you’ve saved or booked are now accessible under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Island paradise at Siesta Key vacation home rentals

Siesta Beach is regularly hailed on lists of the very best in the United States. It strings along Florida's Treasure Coast, fringing the edge of Siesta Key like a wisp of white cloud that's lapped by a sky-blue sea. But the sands aren't the only draw. This barrier isle is also a fun-loving family hotspot, laden with coffee shops and oyster bars, kayak rentals and turtle sanctuaries. Siesta Key vacation rentals cover all sorts, whether you're after a pad overlooking the waves of the Mexican Gulf or a modern apartment that takes the whole crew.

Attractions near your Siesta Key summer rental

There's no doubt about it – the main attraction of Siesta Key is Siesta Beach. That long stretch of sand so white you might just be tempted to spoon it into your morning coffee is regularly hailed as one of the most beautiful in the whole United States. With its aquamarine waters and undulating dunes, it says, "Move over, California!" You could even bag yourself a Siesta Key vacation rental with views over the shoreline, just to make sure you're the first laying down the towel, come morning.

What to do near Siesta Key vacation rentals

Wobbling on a paddle board or blowing bubbles from a snorkeling tube, whizzing on personal watercraft or carving wakes through the Gulf – all sorts of aqua fun is on the menu in Siesta Key. Home to boating outfitters, big fishing tourers, kitesurfing guides and turtle conservationists, this Floridian island is the place to be if you love making a splash. Dolphin cruises and whale spotting usually top the menu for families. A meeting with bottlenoses and beaked whales is all but guaranteed, between December and February.

Something tropical in Siesta Key

The palms and Caribbean-esque sands of Siesta Key should be a clue to the island's tropical nature. Enjoying year-round warmth and 100s of days of sunshine, there's never really a time when the board shorts and bikinis aren't needed. Loads of people will head down during the US winter. Temperatures average around 62–74 between December and March, and there's hardly any rain at all – you'll get a tan while the snows fall in the Midwest. Summer, from June to September, is the hottest time. It also brings more chance of rain and the occasional tropical storm.

Reefs and resplendent sands along Siesta Key

The whole coast of Siesta Key is a patchwork of cotton-white powder and turquoise seas, and a playground for lovers of the beach. You can laze on the brilliant white sands or snorkel through crystal-clear Gulf waters. Talking of the Gulf, there are coral reefs and multicolored fish waiting just off the shore, not to mention pods of whales and dolphins. You can also encounter rare turtles on the appropriately-named Turtle Beach. Alternatively, book your Siesta Key vacation rentals inland, to kayak through Floridian mangroves and creeks.

Best beaches near Siesta Key vacation homes

The beaches of Siesta Key are its biggest draw. Vacation homes are available near beautiful beaches like Siesta Key Beach, a beach of white quartz sand with clear water, playgrounds, and tennis courts, and Crescent Beach, a wide, sandy beach on the Gulf of Mexico with picturesque views. You’ll also enjoy Sarasota Beach, a quiet beach with calm waters perfect for families.

Transportation to and around Siesta Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 7.8 mi (12.5 km) from the city center.

Family activities near Siesta Key vacation rentals

Siesta Key is filled with unique attractions for kids of all ages. Vacation rentals are available near places like South Lido County Park, a waterfront park with swimming, kayaking, bird watching, and trails, and Turtle Beach, a sandy beach with a native population of sea turtles. You’ll also like Livingston’s Amusement Center, a colossal family-friendly activity space with go-karts, billiards, and games, as well as a bar for adults.

Frequently asked questions

What is the best area to stay in Siesta Key, Florida, United States of America when booking a vacation rental?
When considering the best area to stay in Siesta Key, Florida, you'll find that the Crescent Beach neighborhood stands out for its stunning views and vibrant setting. This area boasts a range of vacation rentals, from cozy beachfront cottages to more spacious family homes, making it great for various traveler preferences. One of the top attractions here is the renowned Siesta Key Beach, famous for its soft, powdery white sand and clear turquoise waters, ideal for sunbathing, swimming, or enjoying a leisurely stroll.

Another appealing aspect of Crescent Beach is its proximity to the lively Siesta Key Village, where you can explore charming shops, enjoy delicious dining options, and experience the local nightlife. The vibrant energy of the village complements the serene beach setting, providing a well-rounded vacation experience.
How much does it cost to rent a vacation home in Siesta Key?
Prices for vacation rentals in Siesta Key vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Siesta Key to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Siesta Key vacation house rentals?
You can find great discounts on house rentals in Siesta Key on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Siesta Key?
For renting a beach house in Siesta Key, the area around Siesta Beach is a prime choice, known for its powdery white sands and vibrant setting. Many properties in this vicinity offer amenities such as private pools, outdoor grilling areas, and expansive decks superb for sunbathing or enjoying sunset views. Travelers can expect a variety of accommodations, from spacious family homes to cozy cottages, all designed with comfort in mind.

Another fantastic option is the area near Turtle Beach, which tends to be quieter and offers a more laid-back vibe. Here, beach house rentals often come equipped with features like kayaks for exploring the nearby mangroves, fire pits for evening gatherings, and direct access to the beach, making it ideal for families or groups seeking a serene escape.

Additionally, the northern part of Siesta Key near the village offers a lively option with easy access to local shops, restaurants, and nightlife. Properties in this area frequently include amenities such as beach gear rentals, bicycles for exploring the island, and community pool access. The proximity to the village enhances the vacation experience, providing both convenience and entertainment options.
What is the most popular type of vacation rental accomodation in Siesta Key?
In Siesta Key, condos are the predominant type of vacation rental, with around 2,234 available throughout the area. These condos are often located near the famous Siesta Beach, providing easy access to the sun and sand. Most units include modern amenities such as fully equipped kitchens, spacious living areas, and access to communal pools or beachfront views.

Vacation houses also make a significant offering, with approximately 705 available, suiting families or larger groups seeking more space. These homes often feature multiple bedrooms, private yards, and outdoor patios, making them ideal for gatherings after a day at the beach.
Are there any family house rentals in Siesta Key?
In Siesta Key, Florida, there are numerous family-friendly vacation homes available, with around 2,158 options to choose from. The area is renowned for its beautiful beaches and vibrant setting, making it an ideal spot for families. Many properties feature spacious layouts, full kitchens superb for preparing meals together, and outdoor areas where children can play.

Visitors can find amenities such as private pools, game rooms, and easy access to local attractions like Siesta Beach and the charming Siesta Key Village, where shops and dining options abound. The locale is also close to parks and recreational areas, ensuring plenty of opportunities for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Siesta Key?
In Siesta Key, there are plenty of vacation homes available for rent that come with pools and hot tubs, with approximately 2,935 options to choose from. This beautiful barrier island is renowned for its stunning beaches and laid-back atmosphere, making it an ideal destination for travelers seeking relaxation. Many of the properties feature private pools, inviting hot tubs, outdoor patios, and fully equipped kitchens, superb for enjoying meals in a tranquil setting.

You'll find a range of accommodations in various neighborhoods, including the bustling Siesta Village, which offers easy access to dining and shopping, as well as quieter areas near Crescent Beach. Additional amenities like barbecue grills, lush gardens, and beach gear are often included, enhancing the overall vacation experience.
Can I find long-stay vacation rentals in Siesta Key?
A long-stay vacation rental in Siesta Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Siesta Key?
In Siesta Key, there are numerous pet-friendly house rentals available, with over 500 options for travelers looking to bring their furry friends along. Many of these vacation homes are situated close to the beautiful beaches that Siesta Key is known for, allowing for easy access to sun and sand. Expect amenities such as private pools, fully equipped kitchens, and spacious outdoor areas great for both pets and families to enjoy.

The area offers a relaxed coastal atmosphere, and the nearby Siesta Key Beach is famous for its soft, white sand, making it a popular spot for pet owners to stroll and soak up the sun. Additionally, the local community is pet-friendly, with various parks and pet-friendly establishments, enhancing the overall experience for those traveling with pets.
Are there any remote work vacation rentals in Siesta Key?
In Siesta Key, Florida, there are plenty of options for remote work vacation rentals, with around 3,144 available throughout the area. This beautiful destination offers a variety of properties, many of which are equipped with essential amenities for remote work. Travelers can expect high-speed Wi-Fi, both in-room and in public areas, ensuring a seamless working experience.

Many rentals also come with comfortable living spaces, allowing for a productive work environment while enjoying the coastal lifestyle. Additionally, some properties offer unique amenities such as outdoor spaces, pools, and proximity to the stunning Siesta Key Beach, providing an ideal balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Siesta Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Siesta Key with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Siesta Key?
In Siesta Key, popular vacation rental amenities cater to travelers seeking comfort and convenience. Many rentals include fully equipped kitchens, allowing guests to prepare their own meals while enjoying the local flavors. Onsite parking is also a common feature, making it easy for visitors to explore the area without worrying about parking availability. Coffee and tea makers are typically provided, adding to the homey feel of the accommodations. Given Siesta Key's beautiful beaches, most rentals are located nearby, offering easy access to the sandy shores. Additionally, many properties provide shared pools, superb for relaxing and socializing after a day at the beach.
When is the best time to visit Siesta Key for a vacation rental?
The most popular time to visit Siesta Key for a vacation rental is from January to March, when travelers flock to this beautiful destination in search of sun-soaked relaxation and vibrant beach activities. This peak season offers the best of Florida's warm weather, with temperatures typically ranging from the mid-50s to low 80s Fahrenheit. Visitors can bask in the sunshine, enjoy water sports, or simply unwind on the pristine white sands known for their soft, powdery texture.

During these months, you'll find a lively option as families and couples indulge in outdoor adventures, from paddleboarding in the turquoise waters to exploring the local shops and dining options. The thriving social scene makes it a superb time for those looking to engage with fellow vacationers and soak in the community vibe.

For those seeking a more budget-friendly option, consider planning your visit in November. This month is often less crowded, allowing for a more peaceful experience while still enjoying mild temperatures and beautiful scenery. You can relish the stunning sunsets and partake in quieter beach strolls, making it an ideal choice for those who prefer a more laid-back atmosphere.
How early should I book a Siesta Key vacation rental?
Book your Siesta Key vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Siesta Key, Florida, United States of America?
In Siesta Key, visitors can enjoy a variety of attractions that highlight the area's natural beauty and vibrant culture. Siesta Beach, renowned for its powdery white sand, is a must-visit spot for sunbathing and swimming. The nearby Siesta Key Village offers a lively option with shops, restaurants, and bars, making it ideal for an evening stroll or dining out.

For those interested in outdoor activities, the scenic Turtle Beach is popular for kayaking and paddleboarding, while the Crescent Beach provides a more tranquil setting for relaxation. The Siesta Key Drum Circle, held weekly at the beach, is a unique cultural experience where locals and visitors gather to enjoy music and dance as the sun sets.
Can I change or cancel my Siesta Key home rental booking on Vrbo?
To find Siesta Key vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Siesta Key vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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