Siesta Key vacation rentals

We found 6,430 vacation rentals — enter your dates for availability

Discover a selection of 800 homes, 233 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:Nov 7 - Nov 14
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Find out more about Siesta Key

Find out more about Siesta Key

Why visit Siesta Key

  1. Beautiful Beaches: Siesta Key Beach boasts soft, powdery sands perfect for family outings and relaxation.
  2. Charming Village: Explore Siesta Key Village, filled with friendly locals, vibrant art, and unique shops.
  3. Diverse Accommodations: Choose from a range of vacation rentals, from private homes to cozy condos, all with beach access.
  4. Outdoor Activities: Enjoy family-friendly activities, including water sports, parks, and scenic outdoor adventures.
  5. Relaxing Atmosphere: Experience the perfect blend of tropical vibes and serene relaxation in this idyllic destination.

Popular types of accommodation in Siesta Key

Discover the charm of Siesta Key with our diverse selection of vacation rentals. Whether you prefer a private vacation home, a cozy condo, or a spacious apartment, we have options to suit every traveller. With beach access and a focus on transparency and savings, our Siesta Key vacation rentals promise a memorable getaway. Explore your options and find the perfect spot for your next family adventure or romantic retreat.

  • Houses: The top choice for visitors in Siesta Key, these homes offer spacious and comfortable settings for families, friends, or couples.
  • Condos: A popular option for those seeking convenience and amenities, condos in Siesta Key provide a blend of comfort and luxury.
  • Apartments: Ideal for solo travellers or couples, apartments offer a cozy and intimate setting during your stay.
  • Villas: For a touch of elegance, villas provide upscale accommodations with private spaces and stunning views.
  • Cottages: Charming and quaint, cottages offer a homely atmosphere, perfect for a relaxing getaway.**

Top attractions in Siesta Key

Siesta Key is the perfect destination for a beach getaway, offering a range of family-friendly outdoor activities. Visitors can explore beautiful beaches, urban parks, and vibrant streets, catering to those seeking both relaxation and city experiences. Consider booking beachfront rentals for a memorable stay, and don’t miss out on the opportunity to enjoy a classic beach vacation while soaking up the sun in this charming Florida locale.

  1. Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a quintessential beach experience. Relax, sunbathe, or partake in beach activities while enjoying the vibrant atmosphere.
  2. St. Armands Circle: Just 4.8km from Siesta Key, this charming street boasts upscale shops, delightful restaurants, and a lively ambiance. Perfect for leisurely strolls and indulging in local cuisine.
  3. Point of Rocks: Nestled within Siesta Key, this unique rocky outcrop features stunning coastal scenery and excellent snorkeling opportunities, allowing you to explore vibrant marine life.

Things to do recommended for couples

For a romantic getaway in Siesta Key, indulge in luxury at The Oaks Club, enjoy captivating performances at Beatrice Friedman Symphony Center, or embrace adventure at Evie's Golf Center for a fun round of mini-golf. Each experience offers a unique way to connect as a couple.

Things to do recommended for families

Your family vacation in Siesta Key will be filled with fun activities! Enjoy a game at Ed Smith Stadium, unwind at the Robert L. Taylor Community Complex, and explore the beautiful Canopy Walkway and Boylston Nature Trail for a day of outdoor adventure.

Things to do recommended for groups

Groups visiting Siesta Key can enjoy a night at the Van Wezel Performing Arts Hall for a cultural experience, hike the scenic Sarasota BayWalk for outdoor adventure, or tee off at Stoneybrook Golf & Country Club for a fun day of sports in the sun.

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

When planning your trip, whether you're traveling with a group, family, or pets, or seeking extended stays, it's important to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Siesta Key with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to 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 families, a trip wouldn't be the same without their beloved pets accompanying them. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Siesta Key: If you're seeking 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 include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Siesta Key

Siesta Key, a stunning island destination in Florida, offers a perfect blend of relaxation and tropical vibes. Explore the charming Siesta Key Village, where friendly locals and vibrant art create a welcoming atmosphere. Enjoy the soft sands of Siesta Key Beach, ideal for family-friendly outings. With a variety of vacation accommodations available, your stay promises scenic beauty and outdoor adventures that will leave you rejuvenated and inspired.

  • Sarasota: Sarasota is a vibrant city located approximately 8.0km from Siesta Key, offering visitors a delightful blend of beach and urban experiences. Known for its stunning sandy beaches and family-friendly attractions, Sarasota features a lively downtown area filled with shopping centres, restaurants, and cultural venues. Highlights include the Ringling Museum of Art and the Selby Botanical Gardens, both of which showcase the region’s artistic and botanical treasures. Whether you're looking to relax on the beach or explore the local arts scene, Sarasota has something for everyone.
  • Siesta Key Village: Siesta Key Village is a charming neighbourhood situated within the Siesta Key area, making it an ideal spot for those seeking a beachy, laid-back atmosphere. The village is known for its delightful shops, restaurants, and recreational areas, all within walking distance of the famous Siesta Beach. Families can enjoy the urban parks and engage in various outdoor activities, while foodies will appreciate the diverse dining options. The vibrant atmosphere, combined with the beautiful beach, makes Siesta Key Village a perfect destination for relaxation and family fun.
  • Aloha Kai: Aloha Kai is a scenic neighbourhood nestled in the Siesta Key area, celebrated for its outdoor experiences and family-friendly activities. Visitors can explore nearby beaches, take part in recreational activities, or enjoy a performance at a local theatre. The area also offers opportunities for golfing, making it a great choice for both relaxation and adventure. With its lush surroundings and proximity to family-friendly beaches and urban parks, Aloha Kai provides an inviting atmosphere for visitors looking to immerse themselves in Florida's natural beauty.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 hoping to save on your upcoming trip? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new journeys, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are now neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Why people love visiting lively Siesta Key

Enjoy the live music and other features of Siesta Key. Well known for its beaches, seaside and sporting events, this relaxing city won't disappoint. Siesta Key Beach and Lido Beach are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Siesta Key

Are you hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Siesta Key a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Mote Marine Laboratory & Aquarium (4.1 mi / 6.6 km)
  • Sarasota Jungle Gardens (6.4 mi / 10.3 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 km)
  • Sarasota National Golf Course (20.7 mi / 33.4 km)
  • Islandside Golf Course at Longboat Key Club (4.3 mi / 6.9 km)
  • Harborside Golf Course at Longboat Key Club (4.3 mi / 7 km)

Exploring the beaches and other natural features in Siesta Key

Travelers enjoy Siesta Key for its sunsets, seaside and tropical locale. Whether you're an adventurous traveler or just want to take in the scenery, Siesta Key is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Siesta Key Beach (0.9 mi / 1.5 km)
  • Lido Beach (2.4 mi / 3.9 km)
  • Crescent Beach (2.3 mi / 3.8 km)
  • Point of Rocks (2.7 mi / 4.3 km)
  • Marie Selby Botanical Gardens (3.9 mi / 6.2 km)
  • Turtle Beach (4.4 mi / 7.1 km)

Seasonal weather in Siesta Key

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 82°F.

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.

Frequently asked questions

What is the best area to stay in Siesta Key when booking a vacation rental?
When considering a vacation rental in Siesta Key, Florida, the Crescent Beach area stands out as an excellent choice. This picturesque neighbourhood offers a serene atmosphere, with its stunning white sandy beaches and crystal-clear waters. Guests can enjoy the breathtaking sunsets that Crescent Beach has to offer, making it great for relaxing evenings. The area is also conveniently located near Siesta Key Village, which is brimming with charming shops, delightful restaurants, and lively entertainment options.

Another fantastic option is the Siesta Key Village itself, where you'll find a vibrant atmosphere filled with local culture. Here, visitors can easily access numerous dining options and boutique shops, all within walking distance. Additionally, the iconic Siesta Key Beach is just a stone's throw away, renowned for its powdery sand and water sports activities. The Village hosts various events throughout the year, ensuring there's always something happening to engage visitors.
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 travelling 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.
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, Florida, the area around Siesta Beach is particularly popular. This beach is renowned for its powdery white sand and turquoise waters, making it an ideal spot for sun-seekers and families alike. Many beach houses in this vicinity offer amenities such as private pools, outdoor grilling areas, and spacious decks, superb for enjoying the stunning sunsets.

Nearby, the Crescent Beach area also offers excellent rental options, with properties that often include direct beach access and stunning views of the Gulf of Mexico. These homes frequently come equipped with modern kitchens, multiple bedrooms, and laundry facilities, suiting both short and long-term stays. Find your rental near the beach in Siesta Key.
What is the most popular type of vacation rental accomodation in Siesta Key?
In Siesta Key, condos are the most popular type of vacation rental, with approximately 2,244 available across the area. These condos are often located near the beautiful Siesta Beach and offer a range of amenities including fully equipped kitchens, spacious living areas, and communal swimming pools. Many also feature private balconies or patios where guests can enjoy the sunshine and stunning views.
Are there any family house rentals in Siesta Key?
In Siesta Key, Florida, there are numerous family-friendly house rentals available, with around 2,029 options to choose from. The area is renowned for its stunning beaches and vibrant atmosphere, making it an ideal destination for families seeking a memorable vacation.

Properties often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children to play. Many homes come with amenities such as private pools, game rooms, and easy access to the beautiful Siesta Key Beach, known for its powdery white sand and clear waters. See all family-friendly rentals in Siesta Key.
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 around 2,945 options to choose from. This beautiful coastal destination is renowned for its stunning beaches and relaxed atmosphere, making it an ideal spot for a getaway. The area boasts various neighbourhoods, including the vibrant Siesta Village, where you'll find properties within walking distance to the beach, as well as quieter residential areas that offer more privacy. Find your rental in Siesta Key with a pool or a hot tub.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Siesta Key?
In Siesta Key, there are numerous pet-friendly house rentals available, offering a welcoming environment for both travellers and their furry companions. Many of these properties feature desirable amenities such as private pools, outdoor patios, and fully equipped kitchens, making them superb for families or groups looking to enjoy a beach getaway.

The area is renowned for its stunning beaches, particularly Siesta Beach, which is famous for its powdery white sand and beautiful sunsets. Nearby, you can find dog-friendly parks and beaches, ensuring that your pets can enjoy the outdoors just as much as you do. For instance, Brohard Paw Park, located a short drive away in Venice, is an excellent spot for pets to run freely and socialise. See all pet-friendly rentals in Siesta Key.
Are there any remote work vacation rentals in Siesta Key?
In Siesta Key, Florida, there is a wealth of remote work-friendly vacation rentals available, with around 3,170 options to choose from. This beautiful destination is renowned for its stunning beaches and vibrant atmosphere, making it an ideal spot for those looking to balance work and leisure. Many properties are equipped with dedicated workspaces, including desks, comfortable chairs, and high-speed Wi-Fi, ensuring a productive environment.

Travellers can expect a variety of amenities across different rentals, such as fully equipped kitchens, spacious living areas, and outdoor spaces to unwind after a day of work. Additionally, some properties may offer access to communal business centres and computer stations, making it easy to stay connected. 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 travellers 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 rental amenities include heated pools, kitchens, and shared pools, suiting a variety of traveller needs. Most vacation rentals come equipped with essential kitchen facilities, allowing guests to prepare their own meals. Additionally, many properties feature microwaves, making it convenient for quick snacks or reheating leftovers.
When is the best time to visit Siesta Key for a vacation rental?
The most popular time to visit Siesta Key is during the peak season from January to March, when travellers flock to this beautiful destination seeking sun, sand, and relaxation. This period boasts ideal weather, with average temperatures in the mid to high 20s Celsius, making it great for beach activities and outdoor adventures. The vibrant atmosphere attracts families and couples looking to unwind, as well as those eager to partake in water sports, beach volleyball, and delightful strolls along the famous powdery white sands.

While January is particularly beloved, with its lively beach scene and numerous local events, visiting in November can also be a rewarding experience. During this quieter month, you can enjoy the stunning coastal views and the charm of Siesta Key without the bustling crowds, all while benefiting from more affordable vacation rental options. The weather remains pleasant, allowing for comfortable outdoor exploration and relaxation.
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.
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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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