Vacation rentals in Siesta Key
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Top-rated accommodation in Siesta Key
Guests agree: these stays are highly rated for location, cleanliness and more.
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!
14–21 Nov
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.
13–20 Oct
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!
22–29 Jan
Accommodation for every style
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Popular amenities for Siesta Key accommodation
Other great accommodation in Siesta Key
Guesthouse in Sarasota
4.93 out of 5 average rating, 363 reviewsClean and Modern Sarasota Studio w/ Beach Gear!
1–8 Sep
Apartment in Sarasota
4.98 out of 5 average rating, 164 reviewsGillespie On The Park, Walk to Downtown
21–28 May
Guest suite in Sarasota
4.96 out of 5 average rating, 101 reviewsCozy little guest suite- 6 miles from Siesta Beach
24 Apr – 1 May
Condo in Sarasota
4.96 out of 5 average rating, 119 reviewsLido-Key- Tiny Studio Holiday Cottage-A
30 Aug – 6 Sep
Guest suite in Sarasota
4.94 out of 5 average rating, 254 reviewsTwo Miles to Siesta Key
21–28 Oct
Guesthouse in Osprey
4.99 out of 5 average rating, 281 reviewsCozy Cottage by the Bay
7–14 Apr
Apartment in Siesta Key
4.99 out of 5 average rating, 136 reviewsSiesta Key #1 Beach, pickle ball & tennis paradise
13–20 Mar
Home in Siesta Key
4.93 out of 5 average rating, 104 reviewsSiesta Peace Retreat a private home rental
26 May – 2 Jun
Home in Sarasota
4.98 out of 5 average rating, 196 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
15–22 Oct
Guest suite in Sarasota
4.98 out of 5 average rating, 184 reviewsThe Sapphire Suite 1Bed/1Bath
4–11 Nov
Cottage in Siesta Key
4.94 out of 5 average rating, 66 reviewsSurf Shack- Walk to Village/Boat Dock Included
19–26 Sep
Condo in Siesta Key
4.95 out of 5 average rating, 61 reviewsThe Honeymoon Suite on Siesta Key Beach
8–15 Sep
Quick stats about holiday 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 |
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