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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Cottage in Siesta Key
Adorable Cozy Silver Sands Cottage on Siesta Key!!
1 bedroom, 1 bed, 1 private bathroom
25–30 Jul
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4.88 out of 5 average rating, 194 reviews
Guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Home in Sarasota
Tropical Oasis 4 BR Home w/ Pool & Spa
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Home in Sarasota
Pink House | 12 PPL | Pool | Game Room | BBQ|Patio
4 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
New place to stay
Superhost
Home in Sarasota
Spacious 2BR Retreat w/Large Spool Near Downtown
2 bedrooms, 3 beds, 2 bathrooms
16–21 Jul
New place to stay
Home in Siesta Key
4B Arthouse & Hot Tub | Walk to Siesta Key Beach!
4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
New place to stay
Superhost
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 Aug
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
6 bedrooms, 8 beds, 6.5 bathrooms
15–20 Aug
New place to stay
Top guest favourite
Home in Sarasota
Modern Pool House Sealand 3/2 near Siesta
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 99 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
10–17 Jul
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Anna Maria
Sundowner Beach: Luxury Gulf-front, stunning views
5 bedrooms, 9 beds, 5 bathrooms
11–16 Nov
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds, 2 bathrooms
24–31 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Siesta Key
Villa Margarita - 312
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
New place to stay
Guest favourite
Home in Sarasota
LA Luxury & Heated Pool Oasis 12 min to Siesta Key
4 bedrooms, 2 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 5 reviews