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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Siesta Key Condo. Checkout our great rates!
2 bedrooms, 4 beds, 1.5 private bathrooms
5–12 Sept
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4.96 out of 5 average rating, 135 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
Home in Sarasota
Tropical Oasis 4 BR Home w/ Pool & Spa
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
21–26 Jul
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 Aug
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Top guest favourite
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
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
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
Top guest favourite
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
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
7–14 Jul
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Beach Beach
4.96 out of 5 average rating, 138 reviews, 3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Home in Siesta Key
Villa Fiesta - 312
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
Home in Sarasota
Coastal Calm
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–21 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
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
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
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
Superhost
Home in Palmetto
Fin & Claw at the Dock, Waterfront Luxury Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 8 beds, 3 bathrooms
13–18 Jul