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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 Beach590 locals recommend
Siesta Key Oyster Bar82 locals recommend
Walt's Fish Market Restaurant87 locals recommend
Trader Joe's23 locals recommend
Siesta Key Village24 locals recommend
Captain Curt's Crab & Oyster Bar43 locals recommend

Siesta Key beach vacation rentals

Top guest favorite
An aerial view captures a beachside community with white homes nestled among palm trees. The coastline and ocean are visible in the background, while nearby buildings and roadways provide context for the location. The neatly arranged rooftops highlight the peaceful neighborhood ambiance.
Townhouse in Holmes Beach
4.99 out of 5 average rating, 138 reviews

Summer Discounts Available! Steps from the Beach!

Superhost
A spacious bedroom features a elegant white bedframe with a black-and-white patterned comforter. A lamp sits on a nightstand beside the bed. A ceiling fan is visible above, and natural light enters through a window with multiple panes.
Home in Sarasota
5 out of 5 average rating, 3 reviews

Walk to the beach.

Guest favorite
The open living area features a bright view of the beach through a large window. A round dining table is positioned nearby, complemented by a centerpiece of seashells. Bar seating offers additional space, and light tiles reflect the natural ambiance.
Condo in Treasure Island
4.93 out of 5 average rating, 128 reviews

Beachfront w/ Stunning Sunsets in Prime Location.

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

Superhost
An aerial view captures the condo complex surrounded by green spaces and parking areas. The nearby beach stretches along the coastline, highlighting the inviting atmosphere of Upham Beach. Clear skies and a glimpse of distant buildings add to the spacious scene.
Condo in St. Pete Beach
4.82 out of 5 average rating, 74 reviews

Beach Getaway - 2b /1b Condo

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
4.89 out of 5 average rating, 71 reviews

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

Superhost
A balcony view showcases vibrant palm trees and lush landscaping, with a clear view of the ocean in the distance. The sun shines brightly in a clear blue sky, providing a sense of openness, while the parking area can be seen below.
Condo in Siesta Key
4.67 out of 5 average rating, 3 reviews

Our House at the Beach- Sugar Sands

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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, 28 reviews

Last minute May ,house 2 Mil beach .Pets welcome

Superhost
Home in Venice
4.91 out of 5 average rating, 57 reviews

The Ripple Inn At Fennario

Guest favorite
An aerial view showcases a spacious property featuring a heated private pool and a vibrant pickleball court. A serene pond is visible in the background, surrounded by greenery. The layout includes well-maintained outdoor spaces and convenient access to the home.
Home in Bradenton
4.93 out of 5 average rating, 61 reviews

Pickleball! Pond! Private Heated Pool! Foosball

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 shaded outdoor area is framed by delicate curtains, featuring a vibrant rug and comfortable seating. A television is mounted on the wall, and a dining table is positioned under the cover, providing a relaxing space for guests. Lush greenery and bright blue sky enhance the ambiance.
Home in Siesta Key
4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Top guest favorite
A charming facade of a coastal home is framed by palm trees against a vibrant sunset sky. A paver driveway leads to the entrance, highlighted by a light blue door. Tropical landscaping adds color and texture to the property.
Home in Holmes Beach
5 out of 5 average rating, 65 reviews

Private Luxurious Ground Level Home

Guest favorite
Condo in Sarasota
4.85 out of 5 average rating, 102 reviews

5209B Menorca Street - Siesta Key Village Condo

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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
4.92 out of 5 average rating, 12 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
4.76 out of 5 average rating, 117 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

Guest favorite
A spacious bedroom is furnished with a plush bed dressed in soft neutral tones and decorative pillows. Two bedside tables flank the bed, each holding a lamp. Natural light fills the room, highlighting the warm color palette and elegant bedding.
Home in Port Charlotte
4.9 out of 5 average rating, 42 reviews

Charming home near the Beach and Punta Gorda.

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
4.8 out of 5 average rating, 5 reviews

Amazing Location! Amazing Amenities!

Guest favorite
An aerial view of a large lagoon features an inviting blue water expanse with a sandy beach area. Beach chairs line the shore, and a water slide is visible near a playful water play structure. Lush landscaping surrounds the area, enhancing the recreational environment.
Home in Wimauma
5 out of 5 average rating, 22 reviews

Lagoonside Escape

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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 980 condo rentals to over 420 house 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

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