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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Cottage in Siesta Key
The Marlin: Heated Pool, 4 Houses to Beach
2 bedrooms, 1 bed, 1 private bathroom
3–8 Sept
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4.94 out of 5 average rating, 133 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
4.95 out of 5 average rating, 197 reviews
Top guest favourite
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 102 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
23–30 Aug
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 147 reviews
Guest favourite
Home in Sarasota
New 8/8 bathroom beach house! Heated pool and spa!
8 bedrooms, 10 beds, 8.5 bathrooms
29 Aug – 5 Sept
4.95 out of 5 average rating, 21 reviews
Luxe
Home in Anna Maria
Bridge and Bay Escape - Brand New Listing!
4 bedrooms, 5 beds, 5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Siesta Key
Siesta Key Home: Private Screened Pool
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Siesta Key
Endless Views | Panoramic View of Siesta Beach
3 bedrooms, 3 king beds, 3 bathrooms
28 Aug – 2 Sept
4.2 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 60 reviews