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Search results; Over 1,000 homes in Siesta Key

Guest favorite
Guesthouse in Siesta Key
Saltwater pool and hot tub near Siesta Key
1 bedroom, 1 bed, 1 private bath
Aug 13 – 18
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4.93 out of 5 average rating, 125 reviews
Top guest favorite
Home in Siesta Key
Pool and spa near Siesta Key Beach
5.0 out of 5 average rating, 10 reviews, 5 bedrooms, 7 beds, 5 baths
Sep 24 – 29
Superhost
Chalet in Siesta Key
Walk to the beach and Village
New place to stay, 2 bedrooms, 3 beds, 2 baths
Aug 18 – 23
Apartment in Siesta Key
Private beach and 3 pools in Siesta Key
New place to stay, 2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
Luxe
Home in Bradenton Beach
Rooftop Gulf views, pool, and spa
5.0 out of 5 average rating, 22 reviews, 6 bedrooms, 7 beds, 5.5 baths
Aug 30 – Sep 4
Home in Sarasota
Renovated with 3 heated pools, beach access
New place to stay, 2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
Top guest favorite
Villa in Siesta Key
Beachfront villa with 3 heated pools
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 3 beds, 1 bath
Aug 28 – Sep 2
Top guest favorite
Home in Siesta Key
Private pool, one mile from the beach
4.96 out of 5 average rating, 45 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 30
Home in Sarasota
Heated saltwater pool near Siesta Key
New place to stay, 3 bedrooms, 5 beds, 2 baths
Sep 8 – 13
Top guest favorite
Home in Sarasota
Waterfront pool with waterslide near beach
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 4 baths
Aug 30 – Sep 4
Home in Anna Maria
Pool, hot tub, and canal-side kayaks
New place to stay, 4 bedrooms, 8 beds, 6 baths
Aug 15 – 20
Top guest favorite
Townhouse in Siesta Key
Beach views, 2 blocks from Siesta Key
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 12 – 19
Top guest favorite
Chalet in Siesta Key
100 steps to the beach on Siesta Key
4.93 out of 5 average rating, 60 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 19 – 24
Top guest favorite
Home in Sarasota
Saltwater pool and hot tub near beach
4.95 out of 5 average rating, 37 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Home in Siesta Key
Canal access and pool near Siesta Village
4.67 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 15 – 22
Top guest favorite
Home in Sarasota
Mid-century pad with pool near beach
5.0 out of 5 average rating, 73 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 12 – 17
Home in Siesta Key
Renovated pool home near Siesta Key Village
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Top guest favorite
Condo in Sarasota
Walk to the beach from Siesta Village
4.99 out of 5 average rating, 86 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in Bradenton
Heated pool, 10 min to Anna Maria
4.96 out of 5 average rating, 57 reviews, 2 bedrooms, 3 beds, 2 baths
Dec 1 – 6