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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
2 bedrooms, 3 beds, 2 private bathrooms
4–9 Aug
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4.82 out of 5 average rating, 146 reviews
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
24–29 Aug
Guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
Top guest favourite
Home in Sarasota
Coastal Calm - 3BD/2BA Heated Pool Near Beaches
4.95 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 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
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
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, 7 reviews, 3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
9–16 Jul
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 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 Sarasota
Spacious 2BR Retreat w/Large Spool Near Downtown
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–20 Sept
Superhost
Home in Siesta Key
Villa Fiesta - 312
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 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
1–8 Aug
Guest favourite
Home in Sarasota
Casa Del Sol - 3 Bedrooms/2 Bathrooms (In-law Suite)
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 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
Superhost
Home in Sarasota
6630 - Mira Bella
4 bedrooms, 10 beds, 4 bathrooms
5–10 Aug
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Beach Beach
4.96 out of 5 average rating, 139 reviews, 3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept