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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Cottage in Siesta Key
Cottage on Siesta Key Beach
2 bedrooms, 3 beds, 2 private bathrooms
20–25 Sept
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4.88 out of 5 average rating, 348 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, 8 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, 14 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
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, 16 reviews
Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Bungalow in Sarasota
*Waterfront house with dock and heated pool
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 96 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
Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
4.88 out of 5 average rating, 178 reviews
Guest favourite
Apartment in Sarasota
Direct Gulf View - Residence 603
3 bedrooms, 3 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.93 out of 5 average rating, 60 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds, 5 bathrooms
15–22 Sept
4.98 out of 5 average rating, 51 reviews
Guest favourite
Home in Sarasota
Casa Bella Vita | Walk to Crescent Beach!
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 119 reviews
Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
16–23 Sept
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
16–21 Sept
4.93 out of 5 average rating, 44 reviews