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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Cottage in Siesta Key
Adorable Cozy Silver Sands Cottage on Siesta Key!!
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.87 out of 5 average rating, 199 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sarasota
Brand NEW home! ~Waterslide~Heated Pool~Beach View
8 bedrooms, 9 beds, 8.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds, 2 bathrooms
6–13 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
1 bedroom, 2 beds, 1 bathroom
18–23 Sept
New place to stay
Guest favourite
Apartment in Sarasota
Direct Gulf View - Residence 603
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Sarasota
Luxury Sport Vacation Pool House-Downtown Sarasota
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 44 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds, 5 bathrooms
7–14 Sept
4.98 out of 5 average rating, 50 reviews
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
6–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 396 reviews
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
14–21 Sept
4.95 out of 5 average rating, 198 reviews
Top guest favourite
Apartment in Sarasota
Waterfront w/ Pool, mins to SK Beaches, bikes/sups
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 34 reviews