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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Resort in Siesta Key
The Haven, with heated pool.
1 bedroom, 1 bed, 1 private bathroom
30 Jul – 4 Aug
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5.0 out of 5 average rating, 24 reviews
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
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
Superhost
Home in Siesta Key
Villa Fiesta - 312
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
6–13 Jul
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
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 Aug
Superhost
Home in Sarasota
Pink House | 12 PPL | Pool | Game Room | BBQ|Patio
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
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
Superhost
Home in Siesta Key
Gertrudes Siesta, Beach-view, Pool,1 min to Beach!
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Sarasota
Palm Breeze Haven
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
New place to stay, 6 bedrooms, 8 beds, 6.5 bathrooms
15–20 Aug
Guest favourite
Home in Sarasota
Big backyard hangout, firepit, large primary suite
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Home in Bradenton
Pool & Sand Volleyball | 3 Kings | Near AMI & IMG
4.98 out of 5 average rating, 42 reviews, 4 bedrooms, 5 beds, 3 bathrooms
9–14 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 Palmetto
Fin & Claw at the Dock, Waterfront Luxury Retreat
New place to stay, 4 bedrooms, 8 beds, 3 bathrooms
13–18 Jul
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
Home in Sarasota
Coastal Calm
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
31 Jul – 7 Aug