Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
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Other great vacation rentals in Siesta Key
Condo in Siesta Key
4.89 out of 5 average rating, 151 reviewsCozy Siesta Key studio 5 minute walk to Village
Jul 29 – Aug 5
Condo in Siesta Key
4.9 out of 5 average rating, 203 reviewsSea Club 2 Condo Siesta Key
Aug 9 – 16
Condo in Siesta Key
4.85 out of 5 average rating, 130 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Jun 14 – 21
Condo in Sarasota
4.95 out of 5 average rating, 186 reviewsNewly Renovated + Washer/Dryer- Walk everywhere!
Sep 3 – 10
Condo in Siesta Key
4.96 out of 5 average rating, 273 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 26 – Apr 2
Condo in Siesta Key
4.92 out of 5 average rating, 129 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
Dec 5 – 12
Condo in Siesta Key
4.96 out of 5 average rating, 104 reviewsSiesta Key Condo. Checkout our great rates!
Sep 7 – 14
Condo in Siesta Key
4.83 out of 5 average rating, 122 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Oct 31 – Nov 7
House rentals in Siesta Key
Home in Siesta Key
4.92 out of 5 average rating, 141 reviewsSiesta Key Beach & Village 2BR/2BA Steps to Beach
Dec 5 – 12
Home in Siesta Key
5.0 out of 5 average rating, 122 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Oct 1 – 8
Home in Siesta Key
4.87 out of 5 average rating, 118 reviews"Safe & Clean" Palm Oasis - Relax in comfort!
Apr 30 – May 7
Home in Sarasota
4.96 out of 5 average rating, 111 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Jul 17 – 24
Home in Sarasota
4.92 out of 5 average rating, 187 reviewsCentral Location in Sarasota with bonus amenities
Apr 27 – May 4
Home in Sarasota
4.94 out of 5 average rating, 294 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Oct 3 – 10
Home in Sarasota
4.98 out of 5 average rating, 198 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
Jan 17 – 24
Home in Sarasota
4.9 out of 5 average rating, 131 reviewsThe lovely place getaway-SRQ
Apr 30 – May 7
Siesta Key beach vacation rentals
Guest suite in Sarasota
4.95 out of 5 average rating, 233 reviewsSweet Hideaway Minutes from Siesta Key!
Jun 20 – 27
Guest suite in Siesta Key
4.92 out of 5 average rating, 133 reviewsCozy Studio - 5 min walk to #1 Siesta Key Beach!
Sep 26 – Oct 3
Guest suite in Sarasota
4.88 out of 5 average rating, 336 reviewsPrivate, cozy, studio 2 miles from Siesta Key!
Oct 6 – 13
Apartment in Sarasota
4.84 out of 5 average rating, 290 reviewsSarasota Downtown close to Lido Beach
Jul 10 – 17
Guesthouse in Osprey
4.99 out of 5 average rating, 285 reviewsCozy Cottage by the Bay
Jun 8 – 15
Villa in Siesta Key
4.9 out of 5 average rating, 136 reviewsMermaid Villa Ocean Front!
Oct 12 – 19
Island in Sarasota
4.97 out of 5 average rating, 301 reviews*NEW May SALE! last min CX! Sarasota #1 Luxury *
Nov 17 – 24
Cottage in Siesta Key
4.94 out of 5 average rating, 66 reviewsSurf Shack- Walk to Village/Boat Dock Included
Dec 6 – 13
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 410 house rentals to over 820 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 770 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
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