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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
Private Beach with Loungers · 2 Pools & Bay View
2 bedrooms, 3 beds, 2 private bathrooms
13–18 Aug
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4.97 out of 5 average rating, 129 reviews
Top 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, 6 reviews
Guest favourite
Home in Siesta Key
Waterfront with a pool, dock, and fire pit
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 5 reviews
Home in Bradenton
Resort-style backyard with pool and pickleball
4 bedrooms, 7 beds, 3.5 bathrooms
17–22 Aug
New place to stay
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Home in Sarasota
Heated pool and spa near Siesta Key
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Home in Bradenton
Waterfront farmhouse with pool and boat slip
4 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
New place to stay
Guest favourite
Home in Siesta Key
Private pool and hot tub near beach
4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
4.83 out of 5 average rating, 6 reviews
Superhost
Home in Sarasota
Mid-century modern with pool and fire pit
4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
Home in Bradenton
Pool, golf simulator, sauna, and theater
6 bedrooms, 9 beds, 4 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
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
Top guest favourite
Home in Sarasota
Modern Pool House Sealand 3/2 near Siesta
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.98 out of 5 average rating, 99 reviews
Top guest favourite
Home in Bradenton Beach
Dream State ~ Gulf Front/Across from Beach!
6 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 20 reviews
Home in Anna Maria
Rooftop bay views and a heated pool
6 bedrooms, 8 beds, 6.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
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
7 bedrooms, 12 beds, 5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Sarasota
Heated pool and putting green near beach
4 bedrooms, 10 beds, 4 bathrooms
9–14 Aug