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Vacation rentals in Siesta Key

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Siesta Key vacation rentals

Self check-in
Beachfront
Free parking on premises
Pet friendly
Monthly stays

Stay near Siesta Key's top sights

Siesta Beach798 locals recommend
Siesta Key Oyster Bar167 locals recommend
Walt's Fish Market Restaurant150 locals recommend
Trader Joe's110 locals recommend
Siesta Key Village91 locals recommend
Captain Curt's Crab & Oyster Bar94 locals recommend

Siesta Key beach vacation rentals

Top guest favorite
A comfortable living space features a blue sectional sofa and a patterned armchair, complemented by a wooden coffee table. Light streams in through a window with blinds, while a welcoming entry door adds to the serene ambiance.
Villa in Sarasota
4.96 out of 5 average rating, 169 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Superhost
A panoramic view of a sandy beach extends under a bright blue sky streaked with wispy clouds. Gentle waves lap at the shore, and a few figures can be seen walking along the water's edge. Sunlight highlights the fine, white sand.
Home in Sarasota
4.89 out of 5 average rating, 92 reviews

Renovated Beachhouse Private Beach Access, Unit S

Guest favorite
An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.
Condo in Venice
4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

Guest favorite
A gravel pathway is bordered by ornamental grasses leading to a wooden bench, providing a peaceful outdoor space. Utility poles and nearby houses are visible in the background, with a glimpse of a driveway and a boat in the distance.
Home in Nokomis
4.88 out of 5 average rating, 32 reviews

Beach house

Superhost
A light-filled primary bedroom features a king-size bed with a multicolored striped blanket, positioned near a window showcasing views of the Gulf of Mexico. A ceiling fan is present, and a flat-screen TV is mounted on the wall opposite the bed.
Condo in Sarasota
4.9 out of 5 average rating, 10 reviews

Beachfront - Siesta Key 2 BR walk out to beach

Superhost
A private heated pool is surrounded by a spacious sundeck, featuring a dining table with umbrella and several lounge chairs. Lush tropical landscaping includes colorful plants, enhancing the serene outdoor setting.
Home in Holmes Beach
4.88 out of 5 average rating, 8 reviews

Sunset Beach by Duncan Real Estate

Guest favorite
An aerial view highlights a vibrant yellow building adjacent to a shared pool area, bordered by palm trees. The beach can be seen in the background, showcasing a serene blue ocean and sandy shoreline, with additional homes and greenery surrounding the area.
Condo in Bradenton Beach
4.88 out of 5 average rating, 69 reviews

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

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Private vacation rentals in Siesta Key

Guest favorite
A tranquil beach scene features clear turquoise waters with gentle waves lapping the shore. Several individuals are seen swimming and enjoying the water, while the sandy beach stretches under a blue sky dotted with soft clouds. Sparse greenery lines the beach in the background.
Home in Nokomis
4.93 out of 5 average rating, 27 reviews

Last minute May ,house 2 Mil beach .Pets welcome

Top guest favorite
A sandy path meanders through tall grasses and shrubs, leading towards the calm ocean waves. A clear blue sky stretches overhead, enhancing the natural coastal scenery. The pathway is bordered by wooden fencing, guiding visitors to the beach.
Home in Sarasota
4.97 out of 5 average rating, 237 reviews

Your private retreat near Siesta Key Beach.

Guest favorite
A serene seascape captures the horizon where the sun sets over calm waters. Clouds create a gradient of blues and yellows in the sky, reflecting upon the gentle waves. The coastline is visible in the foreground, enhancing the tranquil setting.
Home in Sarasota
5 out of 5 average rating, 7 reviews

Centrally located beautiful home, be near it all!

Superhost
Home in Venice
4.91 out of 5 average rating, 56 reviews

The Ripple Inn At Fennario

Top guest favorite
Home in Bradenton
4.99 out of 5 average rating, 145 reviews

My Peaceful place on the bay.

Superhost
Home in Siesta Key
5 out of 5 average rating, 3 reviews

Rustic Sands - 650

Guest favorite
A private saltwater pool is featured within a serene setting, surrounded by lush greenery and a white fence. Comfortable lounge chairs are positioned nearby, and a large circular seating area with bright cushions provides additional relaxation space. The sunny atmosphere complements the tranquil environment.
Home in Siesta Key
4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Top guest favorite
Home in Holmes Beach
5 out of 5 average rating, 65 reviews

Private Luxurious Ground Level Home

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House rentals in Siesta Key

Guest favorite
A modern living area is presented with a large sectional sofa arranged around a circular coffee table. A sleek TV is mounted on the wall, and the open kitchen is visible in the background. A dining area with black chairs complements the space, and a colorful mural adorns one wall.
Home in Bradenton
4.9 out of 5 average rating, 10 reviews

Modern Resort-Style Townhouse

Top guest favorite
The entrance of the home is framed by lush greenery and vibrant flowering plants. The façade features large windows that provide ample natural light, while a covered porch welcomes guests. A clear blue sky complements the fresh and inviting exterior.
Home in North Port
4.79 out of 5 average rating, 152 reviews

3 bdrm Pool Home / Quiet Cul De Sac

Guest favorite
A spacious living area is furnished with a dark sectional sofa and a wooden coffee table, adorned with a floral arrangement. Light streams through large windows, brightening the neutral-toned walls and tiled flooring. A dining area with metal chairs is visible in the background.
Home in Sarasota
4.85 out of 5 average rating, 101 reviews

Private back yard. Southgate. 2 bedroom, 2 bath.

Superhost
A newly constructed cottage is showcased, featuring a clean white exterior complemented by a bright blue door. Lush green grass surrounds the property, adding a refreshing touch. A paved pathway leads to the entrance, with tall trees providing shade in the background.
Home in Downtown Sarasota
4.75 out of 5 average rating, 114 reviews

Downtown New Construction House

Guest favorite
A screened lanai encloses a saltwater pool, surrounded by well-maintained landscaping. Lush greenery lines the perimeter, while sunlight filters through the trees, creating a relaxing outdoor space. The structure comprises a combination of stone and glass, ensuring a connection to the natural surroundings.
Home in Sarasota
4.94 out of 5 average rating, 98 reviews

Beautiful heated pool home, minutes from beaches

Top guest favorite
A bright bedroom features a gold metal bed frame draped with a decorative seashell-patterned blanket. A blue-and-white 'Seaside' pillow rests on the bed, alongside a contemporary bedside table with a geometric lamp and a small succulent plant. Sheer yellow curtains allow natural light to filter in.
Home in Sarasota
5 out of 5 average rating, 19 reviews

Elegant Newly Remodelled Spacious HOME

Superhost
A spacious living area features a large sectional sofa and a mounted television, with natural light filtering in through the wide windows adorned with light curtains. A modern kitchen bar with stools is visible in the foreground, providing an open layout for easy movement.
Home in Sarasota
4.75 out of 5 average rating, 4 reviews

Amazing Location! Amazing Amenities!

Guest favorite
A modern living room features a dark sectional sofa adorned with yellow cushions. Two patterned armchairs are positioned nearby. A coffee table sits in front, while a light area rug lies underfoot. Large glass doors open to a screened lanai, allowing natural light to fill the space.
Home in Venice
4.92 out of 5 average rating, 52 reviews

Shell near the Sea, 2-Br Pet Friendly Home

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Quick stats about vacation rentals in Siesta Key

  • Total rentals

    1.8K properties

  • Total number of reviews

    32K reviews

  • Family-friendly rentals

    1.5K properties are a good fit for families

  • Pet-friendly rentals

    330 properties allow pets

  • Rentals with a pool

    1.4K properties have a pool

  • Rentals with dedicated workspaces

    820 properties have a dedicated workspace

Your guide to Siesta Key

All About Siesta Key

Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.

The best time to stay in a vacation rental in Siesta Key

Thanks to the island's location in the Gulf of Mexico, weather conditions and water temperatures are favorable for most of the year. Beginning in March, temperatures start to rise, with averages peaking around mid October. You can expect heat and humidity at your Siesta Key rental during this period, but gulf stream breezes help keep things cool. Weekly farmers markets, a musical festival, and a fireworks show are just a few of the notable events happening through the summer season.

In winter, temperatures see a marginal decrease, with January and February being the coldest months. However, many still find both the air and water temperatures suitable for swimming. The winter also happens to be when many of the area’s art festivals take place. Check out the Chalk Art Festival towards the end of October or the sand sculpture competition in November where you can take sculpting classes and vote on your favorite piece of art.

Top things to do in Siesta Key

Point of Rocks

One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.

Siesta Key Drum Circle

The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.

Deep-sea fishing

Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.

Frequently Asked Questions

  • How is the weather in Siesta Key?

    Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.

  • What are some of the best things to do in Siesta Key?

    Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.

  • What is the best time of year to visit Siesta Key?

    The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.

  • What are the best places to stay in Siesta Key?

    Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.

  • What are the best places to visit in Siesta Key?

    Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.

  • What are some hiking trails in Siesta Key?

    While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.

  • What are some family activities to do in Siesta Key?

    Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.

  • What are some of the best day trip ideas in Siesta Key?

    Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.

  • What types of vacation rentals are available in Siesta Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Siesta Key. From over 420 house rentals to over 980 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Siesta Key?

    Yes! Work meets play with ease at over 820 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key