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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
2 bedrooms, 3 beds, 2 private bathrooms
11–16 Sept
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4.83 out of 5 average rating, 151 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
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 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
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
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 15 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
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds, 2 bathrooms
10–15 Sept
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds, 5 bathrooms
9–16 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Home in Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 16 reviews
Luxe
Home in Sarasota
Gulf View Penthouse | Gulf Views & Hot Tub
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
New place to stay
Guest favourite
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
10–15 Sept
4.93 out of 5 average rating, 44 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
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Guest favourite
Apartment in Siesta Key
Beautiful 3rd Floor Condo facing the Gulf of Mex
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
Luxury Sport Vacation Pool House-Downtown Sarasota
3 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 68 reviews
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 3 reviews