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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Cottage in Siesta Key
Siesta Key Two Bedroom Cottage
2 bedrooms, 2 beds, 1 private bathroom
13–18 Aug
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4.94 out of 5 average rating, 88 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds
18–23 Aug
New place to stay
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds
31 Aug – 5 Sept
4.96 out of 5 average rating, 145 reviews
Top guest favourite
Home in Sarasota
Sarasota Tiki Retreat | Pool Spa Entertainment
3 bedrooms, 6 beds
1–6 Nov
5.0 out of 5 average rating, 11 reviews
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Apartment in Sarasota
Siesta Key 2 bedroom condo w pool arcade pets ok
2 bedrooms, 3 beds
16–21 Aug
4.99 out of 5 average rating, 86 reviews
Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds
28 Aug – 2 Sept
4.48 out of 5 average rating, 61 reviews
Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 5 beds
21–26 Aug
5.0 out of 5 average rating, 167 reviews
Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds
17–24 Sept
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Sarasota
Private Heated Pool~Yacht Rental~BBQ~Near Water
3 bedrooms, 5 beds
8–13 Nov
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds
5–10 Apr
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Sarasota
Fiesta in Siesta Key! Fun & Sun
2 bedrooms, 4 beds
21–26 Nov
4.92 out of 5 average rating, 96 reviews
Top guest favourite
Apartment in Sarasota
5209B Menorca Street - Siesta Key Village Condo
2 bedrooms, 3 beds
17–22 Aug
4.88 out of 5 average rating, 126 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Bradenton Beach
Bradenton Beach Sunsets 2, Anna Maria Island, FL
1 bedroom, 2 beds
16–21 Aug
4.98 out of 5 average rating, 253 reviews
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
24–29 Sept
5.0 out of 5 average rating, 10 reviews
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
29 Aug – 3 Sept
New place to stay
Top guest favourite
Cottage in Sarasota
Cozy Lido Key Studio Steps to Beach & Kayaking
1 bedroom, 1 king bed
6–11 Nov
4.98 out of 5 average rating, 59 reviews