Siesta Key vacation rentals

We found 6,397 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.
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Find out more about Siesta Key

Find out more about Siesta Key

Why visit Siesta Key

  1. Beautiful Beaches: Enjoy the stunning Siesta Key Beach, famous for its powdery white sand and crystal-clear waters.
  2. Outdoor Activities: Engage in snorkeling, kayaking, and exploring nearby state parks and urban parks.
  3. Family-Friendly Atmosphere: Siesta Key offers a welcoming environment perfect for families and friends seeking fun together.
  4. Cultural Experiences: Visit nearby Sarasota for a vibrant arts scene, including galleries, theaters, and museums.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, from beachfront condos to charming cottages.

Popular types of accommodation in Siesta Key

If you're looking for the perfect vacation rental in Siesta Key, we’ve got just what you need. Our most popular accommodations include stunning condos, charming houses, and cozy apartments. Whether you prefer a beach rental, a Pete Beach condo, a quaint Bradenton Beach cottage, or a stylish Lido Key condo, you'll find the ideal spot to unwind. Explore options like Sands Village and make your Siesta Key getaway unforgettable!

  • Condos: The top choice for vacation rentals in Siesta Key, offering modern amenities and stunning views.
  • Houses: Ideal for families or groups seeking space and privacy while enjoying the beach life.
  • Apartments: A convenient option for solo travelers or couples looking for a cozy stay close to attractions.
  • Cottages: Charming and quaint, perfect for those wanting a homey feel near the shoreline.
  • Villas: Luxurious options with ample space and upscale features for a relaxing getaway.**

Top attractions in Siesta Key

Siesta Key is perfect for beach lovers and families seeking outdoor adventures. With stunning beaches, urban parks, and nearby state parks, there’s plenty to explore. Enjoy the beautiful Siesta beaches, try snorkeling at various sites, and immerse yourself in the local outdoor experience. Whether you're traveling with family or friends, Siesta Key offers a delightful vacation filled with sun, sand, and fun activities for everyone.

  1. Siesta Key Beach: Renowned for its powdery white sand and calm turquoise waters, Siesta Key Beach offers a perfect spot for sunbathing, swimming, and beach activities. The vibrant atmosphere makes it a favorite for both relaxation and fun.
  2. St. Armands Circle: A charming shopping and dining district located 3 miles away, St. Armands Circle features unique boutiques and gourmet restaurants, all set against a picturesque backdrop of lush landscaping and lively street performances.
  3. IMG Academy: This prestigious sports academy, located 12 miles from Siesta Key, provides training for athletes of all ages in various sports, offering a glimpse into the dedication and discipline required for athletic excellence.

Things to do recommended for couples

For a romantic getaway in Siesta Key, indulge in luxury at The Oaks Club, enjoy a captivating performance at the Beatrice Friedman Symphony Center, or have fun at Fish Hole Miniature Golf for a playful adventure. Each experience offers a unique vibe for couples to cherish together.

Things to do recommended for families

Your family can enjoy a fun day at Ed Smith Stadium, just 6 miles from Siesta Key, where sports vibes abound. Also, explore Nathan Benderson Park, 10 miles away, for wellness and relaxation, or visit the Robert L. Taylor Community Complex, 7 miles away, for more family-friendly activities.

Things to do recommended for groups

Your group can enjoy a day of shopping at the Mall at University Town Center, catch a show at the Van Wezel Performing Arts Hall, and hike along the scenic Sarasota BayWalk for outdoor adventure and beautiful views, all within a short drive from Siesta Key.

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 apply the appropriate filters to match 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, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Siesta Key with young kids: Traveling with young kids can be a bit difficult. It's important to prioritize their comfort and safety, along with providing suitable 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 feel complete without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Siesta Key: If you're searching for vacation rentals that offer discounts for month-long stays, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Siesta Key

Siesta Key, Florida, offers a perfect blend of relaxation and adventure for beach lovers and families. Explore the stunning Siesta Key Beach, known for its powdery white sand, or venture to nearby Sarasota for vibrant arts and culture. Don't miss Holmes Beach and Longboat Key for their friendly atmospheres and beautiful coastal views. Whether you're seeking a tropical escape or a family-friendly retreat, Siesta Key and its surroundings promise unforgettable experiences.

  • Sarasota: Located a mere 5 miles from Siesta Key, Sarasota is a vibrant city well-known for its stunning beaches and rich cultural scene. Travelers flock here for family-friendly activities and outdoor adventures. The area features an array of shopping options, including a bustling mall center and local boutiques. Highlight attractions include the picturesque family beaches and serene parks, perfect for picnics or leisurely strolls. Sarasota’s blend of relaxed beach vibes and artistic flair makes it an ideal spot for both relaxation and exploration.
  • Bradenton: About 15 miles from Siesta Key, Bradenton offers a charming blend of outdoor recreation and family-friendly attractions. This city is celebrated for its beautiful beaches, golf courses, and sports facilities. Visitors can enjoy educational experiences at local museums or spend a day on the green at one of the many golf courses. The vibrant local scene includes parks and family beaches that provide ample opportunities for relaxation and fun, making Bradenton a great addition to your Siesta Key itinerary.
  • Siesta Key Village: Nestled around Siesta Key, Siesta Key Village is a delightful neighborhood known for its beach-centric lifestyle and family-friendly atmosphere. Just steps from the sandy shores, the village offers a mix of recreational areas, shopping centers, and charming eateries. Visitors can explore local boutiques, enjoy fresh seafood, and unwind on the stunning beaches. The vibrant community vibe combined with the beautiful parks makes Siesta Key Village a must-visit spot for those looking to immerse themselves in the local culture and enjoy the sunny Florida weather.

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 HighAverage
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageSlightly High
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 HighAverage
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 LowSlightly Low
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save money on your next getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, OneKey, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Sign up now to start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last stopped, or manage and review your itineraries. You'll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 when booking a vacation rental?
When choosing a vacation rental in Siesta Key, Florida, one of the best areas to consider is Siesta Village. This charming neighborhood offers a vibrant atmosphere with an array of shops, restaurants, and bars, making it easy to enjoy a leisurely stroll. The proximity to Siesta Beach, known for its powdery white sand and stunning sunsets, makes it an ideal spot for beach lovers. You'll find a variety of vacation properties here, ranging from cozy cottages to modern condos, providing ample options for different group sizes and budgets.

Another appealing area is the Crescent Beach section, which is quieter and more residential, superb for those seeking relaxation. This beach is often less crowded than Siesta Beach, allowing for a more tranquil experience while still being close to the action. Guests can enjoy the breathtaking views and easy access to the water, making it a great choice for families or couples. There are numerous vacation rentals available here, providing a unique blend of comfort and proximity to nature.

Lastly, the northern part of Siesta Key, near the North Siesta Key Beach, offers a more laid-back vibe with beautiful scenery and a peaceful atmosphere. This area is ideal for those who wish to escape the hustle and bustle while still being close to attractions like the famous Turtle Beach, known for its shelling opportunities. The variety of vacation rentals in this area caters to those looking for a serene retreat amidst the beauty of Florida's coast.
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, Florida, the area around Siesta Beach is a prime choice, known for its powdery white sand and turquoise waters. Many vacation rentals here feature amenities such as private balconies with ocean views, outdoor grills, and easy beach access, making them superb for families or groups looking to enjoy the sun and surf.

The northern part of Siesta Key, near Crescent Beach, offers a more tranquil experience, with properties often showcasing lush landscaping, private pools, and direct beach access. These rentals frequently come equipped with modern kitchens, spacious living areas, and sometimes even complimentary beach gear, ensuring a comfortable stay.

Additionally, the Gulfside area is popular for its proximity to local shops and dining options, providing convenience for travelers. Many homes in this area boast outdoor spaces like patios or decks, ideal for enjoying sunset views or alfresco dining. 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 vacation rental option, with around 2,228 available throughout the area. These condos are typically located near the beach, providing easy access to the pristine sands and vibrant local atmosphere. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and often private balconies or patios where they can enjoy ocean views or sunset vistas.

Vacation houses are also a significant choice, with about 739 options available, ideal for families or larger groups. These homes generally feature multiple bedrooms, full kitchens, outdoor spaces with BBQ grills, and sometimes private pools, making them superb for gatherings after a day at the beach. Additionally, there are around 199 villas and 187 apartments, suiting those looking for a more upscale or intimate experience, while a smaller selection of 24 cottages offers a charming, rustic feel.
Are there any family house rentals in Siesta Key?
In Siesta Key, Florida, there are numerous family-friendly house rentals available—nearly 2,000 options throughout the area. This beautiful seaside locale features homes in neighborhoods such as Siesta Village and the more tranquil Midnight Pass, both of which offer easy access to the stunning Siesta Key Beach, known for its powdery white sand and gentle waves.

Properties in Siesta Village often come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor patios or decks great for barbecues. Many of these homes also include amenities like private pools, game rooms, and laundry facilities, enhancing the comfort for families traveling together.

On the other hand, rentals near Midnight Pass tend to provide a quieter atmosphere, with some offering private beach access and serene views of the surrounding 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 feature pools and hot tubs, with around 2,883 options to choose from. This beautiful barrier island is renowned for its stunning beaches and laid-back atmosphere, making it a popular destination for travelers.

You can expect a variety of amenities in these properties, including private swimming pools, relaxing hot tubs, and spacious outdoor areas great for sunbathing or entertaining. Many rentals also come with fully equipped kitchens, allowing guests to prepare meals at their leisure, as well as comfortable living spaces to unwind after a day at the beach. 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. 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, travelers can find a substantial number of pet-friendly house rentals, with around 488 options available. This charming coastal destination is known for its stunning white sandy beaches and vibrant local culture, making it an ideal spot for those looking to vacation with their pets. Many of the house rentals in the area come equipped with desirable amenities such as private pools, outdoor patios, and fully furnished kitchens, ensuring a comfortable stay for both guests and their furry companions.

The area surrounding Siesta Key is dotted with parks and pet-friendly beaches, providing ample opportunities for outdoor activities with pets. Siesta Beach itself allows pets on certain sections, making it a great place for long walks and playtime in the sand. Additionally, nearby parks like Phillippi Estate Park offer scenic walking trails and picnic areas, superb for enjoying a day out with your pet. See all pet-friendly rentals in Siesta Key.
Are there any remote work vacation rentals in Siesta Key?
In Siesta Key, there are numerous vacation rentals that cater to remote work needs, with around 3,045 options available. This idyllic coastal destination offers properties that are well-equipped for professionals looking to balance work and leisure. Many rentals feature dedicated office spaces or desks, high-speed Wi-Fi, and comfortable workstations, allowing for productivity even while on vacation.

The area is known for its stunning beaches, particularly Siesta Beach, famous for its powdery white sand and vibrant sunsets, providing a superb backdrop for relaxation after work. Additionally, the nearby village of Siesta Key boasts charming shops, restaurants, and local attractions, creating a lively atmosphere for downtime. Travelers can expect amenities like fully equipped kitchens, outdoor seating areas, and sometimes even pool access, enhancing the overall experience. 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 rental amenities include WiFi, kitchens, and access to heated pools, with many properties featuring shared pool facilities. These amenities cater to travelers looking for comfort and convenience, allowing them to prepare meals and stay connected while enjoying the beautiful surroundings.
When is the best time to visit Siesta Key for a vacation rental?
The best time to visit Siesta Key for a vacation rental is during the peak season from January to March. This period attracts travelers seeking sunny escapes to enjoy the pristine beaches, vibrant local culture, and a host of outdoor activities. With temperatures typically ranging from the mid-60s to the mid-70s Fahrenheit, you can comfortably spend your days lounging on the world-famous Siesta Beach or exploring the nearby nature trails.

January stands out as a popular month, providing a superb blend of mild winter weather and an engaging atmosphere. Visitors can partake in a variety of water sports, from paddleboarding to kayaking, while also enjoying the lively local events and festivals that often take place during this time.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, with fewer tourists and the added bonus of beautiful weather, ideal for beach walks and exploring the charming shops and restaurants without the crowds.
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?
In Siesta Key, visitors can discover a variety of attractions that highlight the area's natural beauty and vibrant culture. The renowned Siesta Beach, famous for its powdery white sand, offers a great spot for sunbathing and swimming. Nearby, the Siesta Key Village features charming shops, restaurants, and nightlife options, making it a lively hub for both relaxation and entertainment.

For nature enthusiasts, the nearby Turtle Beach provides a more secluded experience with opportunities for kayaking and fishing. The area's beautiful sunsets can be enjoyed from the public beach accesses or waterfront dining spots.
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 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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