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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 4 beds, 1.5 private bathrooms
6–11 Aug
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5.0 out of 5 average rating, 163 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 Sarasota
Spacious 2BR Retreat w/Large Spool Near Downtown
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
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
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
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
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
Superhost
Home in Sarasota
Key Life Cove Entire Duplex Near Crescent Beach
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
31 Jul – 5 Aug
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 4 bathrooms
18–25 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
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
4.97 out of 5 average rating, 29 reviews, 3 bedrooms, 6 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
4.96 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Sarasota
The Palms Away
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Aug
Superhost
Home in Bradenton
Sleeps 24 · Heated Pool · Pickleball · Arcade
5.0 out of 5 average rating, 4 reviews, 7 bedrooms, 12 beds, 5 bathrooms
7–12 Jul