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Search results; Over 1,000 homes in Siesta Key

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Siesta Key
On the Beach; Siesta Key SunBum Studio
Studio, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 387 reviews
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
Guest favourite
Home in Siesta Key
Waterfront with a pool, dock, and fire pit
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Home in Bradenton
Pool, Hot Tub, PickleBall, Firepit, 5 min to IMG
New place to stay, 4 bedrooms, 7 beds, 3.5 bathrooms
17–22 Aug
Home in Bradenton
Waterfront farmhouse with pool and boat slip
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
Home in Sarasota
Tropical Oasis 4 BR Home w/ Pool & Spa
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Top guest favourite
Home in Sarasota
Floor-to-ceiling library with a piano
4.96 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Superhost
Home in Sarasota
Mid-century modern with pool and fire pit
New place to stay, 4 bedrooms, 4 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, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Nov – 3 Dec
Guest favourite
Home in Sarasota
Resort-style pool and spa with privacy
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Bradenton
Private Resort-Style Retreat Near IMG and AMI!
New place to stay, 6 bedrooms, 9 beds, 4 bathrooms
10–15 Aug
Top guest favourite
Home in Sarasota
Modern pool home near Siesta Key
4.98 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
Superhost
Apartment in Sarasota
Unobstructed Gulf views from the 5th floor
4 bedrooms, 4.5 bathrooms
1–6 Sept
Superhost
Home in Bradenton
Private resort with pool and pickleball
5.0 out of 5 average rating, 5 reviews, 7 bedrooms, 12 beds, 5 bathrooms
2–7 Aug
Top guest favourite
Home in Bradenton Beach
Dream State ~ Gulf Front/Across from Beach!
5.0 out of 5 average rating, 20 reviews, 6 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
Superhost
Home in Sarasota
Heated pool and putting green near beach
4 bedrooms, 10 beds, 4 bathrooms
9–14 Aug
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
5.0 out of 5 average rating, 3 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
24–29 Aug