Siesta Key vacation rentals

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Popular amenities for Siesta Key vacation rentals

Stay near Siesta Key's top sights

Siesta Beach797 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

Quick stats about vacation rentals in Siesta Key

  • Total rentals

    1.8K properties

  • Total number of reviews

    32K reviews

  • Family-friendly rentals

    1.4K 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

    750 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 930 condo rentals to over 410 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 750 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