Siesta Key vacation rentals
Book unique condos, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Siesta Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Siesta Key vacation rentals
Siesta Key beach vacation rentals
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
Rental unit in Downtown Sarasota
Sarasota Downtown close to Lido Beach
Condo in Lido Key
Lido-Key- Tiny Studio Holiday Cottage-A
Condo in Siesta Key
Siesta Key Ground Floor Condo 2BR On Trolley Line
Villa in Siesta Key
Mermaid Villa Ocean Front!
Cottage in Nokomis
Staycation Sanctuary - 100% Smoke-Free Property
Island in Sarasota
*5 STAR Aug 20 % SALE Sarasota #1 Lux BEACH Villa
Condo in Longboat Key
Relax on LBK!
Siesta Key condo rentals
Condo in Siesta Key
Sea Club 2 Condo Siesta Key
Condo in Siesta Key
Siesta Gardens @ Siesta Key Village
Condo in Siesta Key
Bright and Beachy - Steps to the Water!
Condo in Siesta Key
*A Stones Throw from #1 Voted Siesta Key Beach*
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
Condo in Siesta Key
[Sunny in Siesta] King bed+5 minute walk to beach
Condo in Siesta Key
Private Beach Siesta Key Resort Jamaica Royale
Condo in Sarasota
Beachside Siesta Key Cottage steps from the ocean
Siesta Key home rentals
Home in Sarasota
Stunning Luxe Casita- Gateway to Siesta Beach
Home in Sarasota
☀Coastal Gem☀Heated pool & amazing location!☀
Home in Sarasota
The Key Lime Cottage 2 miles from Siesta Key Beach
Home in Arlington Park
Hyde Park/Southside Village Modern 5 Star Home
Home in Sarasota
Newly Renovated Ranch Minutes From Beach/Downtown
Home in Siesta Key
One-of-a-kind*Beach, Village, Dock & Private Pool!
Home in Sarasota
Sarasota Florida -Wild Orchid Creek Cottage Home
Home in Laurel Park
❤ Villa & Garden in Downtown ~ 5 Min to Beaches
Quick stats about vacation rentals in Siesta Key
Total rentals
1.7K properties
Rentals with dedicated workspaces
770 properties have a dedicated workspace
Rentals with a pool
1.3K properties have a pool
Pet-friendly rentals
350 properties allow pets
Family-friendly rentals
1.4K properties are a good fit for families
Total number of reviews
29K reviews
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 820 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 770 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Destinations to explore
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Naples Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Rentals with a fire pit Siesta Key
- Wheelchair accessible rentals Siesta Key
- Cottage rentals Siesta Key
- Beachfront rentals Siesta Key
- Family-friendly rentals Siesta Key
- Beach house rentals Siesta Key
- House rentals Siesta Key
- Rentals with pools Siesta Key
- Bungalow rentals Siesta Key
- Fitness-friendly rentals Siesta Key
- Monthly Rentals Siesta Key
- Condo rentals Siesta Key
- Rentals with a hot tub Siesta Key
- Rentals with a sauna Siesta Key
- Waterfront rentals Siesta Key
- Apartment rentals Siesta Key
- Townhouse rentals Siesta Key
- Kid-friendly rentals Siesta Key
- Beach condo rentals Siesta Key
- Pet-friendly rentals Siesta Key
- Rentals with a washer and dryer Siesta Key
- Rentals with a kayak Siesta Key
- Rentals with a fireplace Siesta Key
- Rentals with beach access Siesta Key
- Rentals with breakfast Siesta Key
- Villa rentals Siesta Key
- Rentals with outdoor seating Siesta Key
- Rentals with a patio Siesta Key
- Mansion rentals Siesta Key
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom