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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Siesta Key Condo. Checkout our great rates!
2 bedrooms, 4 beds, 1.5 private bathrooms
5–12 Sept
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4.96 out of 5 average rating, 134 reviews
Home in Sarasota
Poppie’s House
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jun
New place to stay
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds, 4 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Apartment in Siesta Key
2 Bedroom, 1 bath, sleeps 5 in Siesta Key #118
2 bedrooms, 3 beds, 1 bathroom
21–28 Jun
New place to stay
Top guest favourite
Home in Bradenton
NEW Canal Family Home - Pool, Kayaks, Game Room
4 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Home in Sarasota
Modern Sarasota Retreat
4 bedrooms, 7 beds, 3.5 bathrooms
20–25 Jun
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4 bedrooms, 5 beds, 4 bathrooms
20–25 Jun
4.88 out of 5 average rating, 8 reviews
Superhost
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Siesta Key
Southern Exposure~2 Homes from Beach! Heated Pool!
6 bedrooms, 6 beds, 4 bathrooms
21–26 Jun
5.0 out of 5 average rating, 21 reviews
Luxe
Home in Siesta Key
400ft to Beach, Ocean View, Pool, in the Village
6 bedrooms, 10 beds, 7 bathrooms
21–26 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Sarasota
Beautifully updated home 7 min to Siesta Key Beach
2 bedrooms, 2 king beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Sarasota
Big backyard hangout, firepit, large primary suite
3 bedrooms, 3 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Oasis-Siesta Beach Beac-3BR/2BA
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 136 reviews
Superhost
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds, 6.5 bathrooms
21–26 Jun
Superhost
Home in Bradenton
Luxury Estate w/ Amazing Outdoor Space, Slps 24
7 bedrooms, 12 beds, 5 bathrooms
22–27 Jun
New place to stay
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Home in Sarasota
Salt & Sun Sarasota
3 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
5.0 out of 5 average rating, 8 reviews
Home in Sarasota
Palm Breeze Haven
4 bedrooms, 6 beds, 3 bathrooms
27 Jun – 2 Jul
5.0 out of 5 average rating, 4 reviews