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Search results; Over 1,000 homes in Siesta Key

Superhost
Apartment in Siesta Key
Siesta Key Beach Front Condo
2 bedrooms, 3 beds, 2 private bathrooms
6–13 Aug
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4.9 out of 5 average rating, 130 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Top guest favourite
Apartment in Siesta Key
On the Beach; Siesta Key SunBum Studio
4.97 out of 5 average rating, 385 reviews, 2 beds, 1 bathroom
18–23 Aug
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 4 beds, 4 bathrooms
19–24 Aug
Top guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Home in Sarasota
Dream's Corner Cove
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
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Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
4.98 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
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Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
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Flat in Siesta Key
Beach Walk Bungalow
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
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Home in Sarasota
The Bradford Cottage/Heated Pool /Mins to Siesta
4.98 out of 5 average rating, 207 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
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Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
4.93 out of 5 average rating, 58 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
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Apartment in Siesta Key
Beachfront Siesta Key - 3 night min w/beach gear!
4.99 out of 5 average rating, 70 reviews, 2 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
4.89 out of 5 average rating, 45 reviews, 3 bedrooms, 7 beds, 2 bathrooms
14–19 Aug
Guest favourite
Home in Sarasota
Heated Pool Siesta Key 4 miles Dtown 6 miles
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
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Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–20 Sept
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Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
4.94 out of 5 average rating, 150 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept