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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
2 Bed/2 Bath Condo Resort View on Siesta Key Beach
2 bedrooms, 3 beds, 2 private bathrooms
8–13 Aug
,
4.93 out of 5 average rating, 152 reviews
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 5 reviews
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
6 bedrooms, 8 beds
15–20 Aug
New place to stay
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
3 bedrooms, 5 beds
13–20 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms
26–31 Aug
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 reviews
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
4 bedrooms, 4 beds
20–25 Jul
New place to stay
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds
6–13 Jul
Top guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds
3–8 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Siesta Key
Villa Fiesta - 312
2 bedrooms, 3 beds
12–17 Jul
New place to stay
Superhost
Home in Sarasota
Pink House | 12 PPL | Pool | Game Room | BBQ|Patio
4 bedrooms, 6 beds
26–31 Jul
New place to stay
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
8–15 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sarasota
Palm Breeze Haven
4 bedrooms, 6 beds
4–9 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Sarasota
Luxury Lido Escape w/ Pool, Slide, Spa & Rooftop!
8 bedrooms, 8 beds
5–10 Jul
4.92 out of 5 average rating, 13 reviews
Superhost
Home in Bradenton
Sleeps 24 · Heated Pool · Pickleball · Arcade
7 bedrooms, 12 beds
7–12 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds
18–23 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Siesta Key
Gertrudes Siesta, Beach-view, Pool,1 min to Beach!
3 bedrooms, 5 beds
8–13 Aug
New place to stay
Superhost
Home in Palmetto
Fin & Claw at the Dock, Waterfront Luxury Retreat
4 bedrooms, 8 beds
13–18 Jul
5.0 out of 5 average rating, 3 reviews