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Search results; Over 1,000 homes in Siesta Key

Top guest favorite
Condo in Siesta Key
Beach-to-bay resort on Siesta Key
2 bedrooms, 3 beds, 2 private baths
Sep 13 – 18
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4.94 out of 5 average rating, 172 reviews
Top guest favorite
Home in Sarasota
Heated saltwater pool near Siesta Key
4.96 out of 5 average rating, 45 reviews, 3 bedrooms, 6 beds, 2 baths
Sep 28 – Oct 3
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
Home in Sarasota
Heated saltwater pool near Siesta Key
New place to stay, 3 bedrooms, 5 beds, 2 baths
Sep 8 – 13
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
Home in Sarasota
Renovated with 3 heated pools, beach access
New place to stay, 2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
Guest favorite
Home in Sarasota
Private pool, fire pit, and hammocks
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 22 – 27
Top guest favorite
Cottage in Sarasota
Renovated with a patio near Lido Beach
4.98 out of 5 average rating, 59 reviews, 1 bedroom, 1 bed, 1 bath
Nov 6 – 11
Top guest favorite
Home in Sarasota
Heated pool and fire pit near Pinecraft
4.83 out of 5 average rating, 40 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 20 – 25
Top guest favorite
Home in Sarasota
Heated pool and fire pit near Siesta Key
5.0 out of 5 average rating, 23 reviews, 4 bedrooms, 7 beds, 2 baths
Sep 7 – 12
Guest favorite
Home in Sarasota
Resort-style pool and spa with privacy
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 baths
Mar 29 – Apr 3
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
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
Villa in Siesta Key
Modern coastal villa near the beach
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 1 – 8
Top guest favorite
Cottage in Bradenton Beach
Water-view cottage across from the beach
4.98 out of 5 average rating, 253 reviews, 1 bedroom, 2 beds, 1 bath
Aug 16 – 21
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
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 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