Siesta Key vacation rentals
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Top-rated vacation rentals in Siesta Key
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Guest suite in Sarasota
4.94 out of 5 average rating, 471 reviewsStudio Apartment. Priv Yard. 5 min to Siesta Key!
Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!
Nov 14 – 21
Guesthouse in Sarasota
4.93 out of 5 average rating, 448 reviewsLa Casetta: "the little house" near to the beaches
La Casetta means, in Italian, a tiny house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.
Oct 13 – 20
Island in Sarasota
4.97 out of 5 average rating, 298 reviews*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!
Jan 22 – 29
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
Guesthouse in Osprey
4.99 out of 5 average rating, 281 reviewsCozy Cottage by the Bay
Apr 7 – 14
Condo in Sarasota
4.96 out of 5 average rating, 119 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Aug 30 – Sep 6
Apartment in Siesta Key
4.99 out of 5 average rating, 135 reviewsSiesta Key #1 Beach, pickle ball & tennis paradise
Mar 13 – 20
Home in Siesta Key
4.93 out of 5 average rating, 104 reviewsSiesta Peace Retreat a private home rental
May 26 – Jun 2
Guest suite in Sarasota
4.94 out of 5 average rating, 279 reviewsBeach & Town Posh Location! Jungle Paradise Studio
Jul 18 – 25
Apartment in Sarasota
4.89 out of 5 average rating, 582 reviewsCharming Apt. in old Florida home
Sep 16 – 23
Guest suite in Siesta Key
4.92 out of 5 average rating, 129 reviewsCozy Studio - 5 min walk to #1 Siesta Key Beach!
Sep 18 – 25
Apartment in Sarasota
4.86 out of 5 average rating, 286 reviewsSarasota Downtown close to Lido Beach
May 29 – Jun 5
Condo in Siesta Key
4.95 out of 5 average rating, 148 reviewsWalk to Siesta Key Village and Beach
Aug 21 – 28
Home in Siesta Key
4.92 out of 5 average rating, 138 reviewsSiesta Key Beach & Village 2BR/2BA Steps to Beach
Jul 25 – Aug 1
Condo in Siesta Key
4.96 out of 5 average rating, 104 reviewsSiesta Key Condo. Checkout our great rates!
Sep 10 – 17
Home in Bradenton
4.97 out of 5 average rating, 189 reviewsHome near Anna Maria Beach - Hot Tub + Fire Pit
Dec 4 – 11
Siesta Key home rentals
Home in Sarasota
4.98 out of 5 average rating, 196 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
Oct 15 – 22
Home in Sarasota
4.91 out of 5 average rating, 142 reviewsSunshine Suite, Minutes to Beach,Tropical Paradise
Nov 3 – 10
Home in Sarasota
4.96 out of 5 average rating, 107 reviewsNewly Renovated Ranch Minutes From Beach/Downtown
Sep 10 – 17
Home in Sarasota
4.96 out of 5 average rating, 127 reviewsSarasota Florida -Wild Orchid Creek Cottage Home
Jul 19 – 26
Home in Sarasota
4.96 out of 5 average rating, 238 reviewsLovely guest house
Jul 22 – 29
Home in Sarasota
4.87 out of 5 average rating, 201 reviewsThe Pineapple Suite.Teal tropical home in Sarasota
May 9 – 16
Home in Siesta Key
4.89 out of 5 average rating, 102 reviewsSiesta Key, FL - Casa Berano
Jun 7 – 14
Home in Siesta Key
4.87 out of 5 average rating, 118 reviews"Safe & Clean" Palm Oasis - Relax in comfort!
Oct 21 – 28
Home in Sarasota
4.85 out of 5 average rating, 161 reviewsAuthentic Florida Bungalow near Downtown and Beach
Apr 29 – May 6
Home in Sarasota
4.94 out of 5 average rating, 124 reviewsRanch 2 blocks from Sarasota Bay
Dec 15 – 22
Home in Sarasota
4.94 out of 5 average rating, 292 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Jun 30 – Jul 7
Home in Sarasota
4.87 out of 5 average rating, 128 reviews5 minutes to private Siesta Key Beach + 2 pools
Nov 26 – Dec 3
Siesta Key villa rentals
Villa in Sarasota
4.96 out of 5 average rating, 130 reviewsNewly Renovated- 150 Yards to Beach & Restaurants!
Jan 10 – 17
Villa in Siesta Key
4.9 out of 5 average rating, 133 reviewsMermaid Villa Ocean Front!
Sep 21 – 28
Villa in Sarasota
4.89 out of 5 average rating, 181 reviewsEntire Standalone Villa,1.2k sf,1 block Lido Beach
Sep 13 – 20
Villa in Sarasota
4.9 out of 5 average rating, 176 reviewsHansen- Gorgeous 3BR/2BA Villa near Siesta Key
Jul 14 – 21
Villa in Sarasota
4.77 out of 5 average rating, 120 reviewsAloha Villa Pet Friendly 3 miles to Siesta Key #2
Sep 24 – Oct 1
Villa in Bradenton
4.83 out of 5 average rating, 133 reviewsElegant private home 3Bdr/3bth
Jun 29 – Jul 6
Villa in Siesta Key
4.92 out of 5 average rating, 49 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
Sep 3 – 10
Villa in Sarasota
5.0 out of 5 average rating, 18 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
Jan 6 – 13
Villa in Sarasota
4.93 out of 5 average rating, 14 reviewsRelaxation awaits in this bohemian inspired villa
Aug 6 – 13
Villa in Sarasota
5.0 out of 5 average rating, 18 reviewsNEW-Cheerful 2-bedroom villa-13 min. to Siesta Key
May 2 – 9
Villa in Sarasota
4.96 out of 5 average rating, 28 reviewsVillage Des Pins - 2 bedroom 2 bath villa
Aug 13 – 20
Villa in Sarasota
4.9 out of 5 average rating, 20 reviewsBeautiful House w/ Pool, 10 Min to Siesta Beach
Aug 5 – 12
Quick stats about vacation rentals in Siesta Key
Total rentals | 1.6K properties |
---|---|
Rentals with dedicated workspaces | 680 properties have a dedicated workspace |
Rentals with a pool | 1.2K properties have a pool |
Pet-friendly rentals | 340 properties allow pets |
Family-friendly rentals | 1.3K properties are a good fit for families |
Total number of reviews | 28K 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 400 house rentals, over 80 villa rentals to over 790 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 680 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
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