Siesta Key vacation rentals

We found 6,358 vacation rentals — enter your dates for availability

Discover a selection of 782 homes, 217 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 most popular type of vacation rental accommodation in Siesta Key?
Based on our data, condos are the most desirable property type in Siesta Key. But as you’d expect, everyone’s idea of the perfect trip differs. Vrbo has vacation rentals with every shape, size and budget in mind, so you’re sure to discover your ideal match.
How much does it cost to rent a vacation rental in Siesta Key?
A range of things can affect what you’ll pay for a vacation rental in Siesta Key, including the length of stay, type of property and season. Still, all Vrbo homes have something in common — exceptional value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Siesta Key?
The average price for a vacation rental by the beach in Siesta Key depends on when you’re visiting the area and the size and type of property you’re looking for. Find prices easily and quickly on Vrbo by entering the dates you’ll be traveling. Then use our filter tool to select the number of bedrooms and amenities that you need, like WiFi, air conditioning and a hot tub.
What are popular rental amenities in Siesta Key?
When it comes to rental amenities that guests search for in Siesta Key, a chef, an ocean view and a barbecue grill are the most popular. With Vrbo vacation homes, there are choices to suit your style and taste, whether you’re taking a trip with relatives, friends or even pets.
What are the top attractions for families in Siesta Key?
There are lots of exciting things to do and see with the family in Siesta Key, such as:

  • St. Boniface Episcopal Church Labyrinth
  • Jim Neville Marine Preserve
  • Point of Rocks

Can I find two-bedroom vacation rentals in Siesta Key?
Take your pick of 1,724 two-bedroom vacation rentals in Siesta Key. Put the kids in the second room or fill it with a couple of your best friends. There’s ample space for whoever’s fortunate enough to come along for the ride.
Are there vacation rentals with WiFi in Siesta Key?
Siesta Key has 749 vacation rentals with WiFi, so you can stay connected while you’re on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to catching up on social media, these Vrbo homes will keep you online.
How old do you have to be to rent a vacation rental in Siesta Key?
You should check with the Siesta Key vacation home you’re looking at on Vrbo as the minimum age varies. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Siesta Key for?
The amount of time you can rent a Siesta Key vacation home for is up to the property. Just put in your preferred travel dates to view options offering extended stays. They include the things you need to make your extended getaway more comfortable and convenient, such as kitchens and backyards. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Siesta Key?
Whether you’re interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fantastic bargains and discounts on Vrbo. From weekend trips to extended vacations, we’ve got the perfect place for your next Siesta Key escape.

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