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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Resort in Siesta Key
Siesta Key Cabana pool side
2 bedrooms, 1 bed, 2 private bathrooms
25–30 Sept
,
5.0 out of 5 average rating, 19 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
Townhouse in Siesta Key
3 bdrm 4 bath Beachhouse
3 bedrooms, 4 beds, 3.5 bathrooms
21–28 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, 14 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.93 out of 5 average rating, 60 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
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
Apartment in Sarasota
Casa Mar 35 2BR Gulfview Stay - Siesta Key Views
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Sarasota
St Armands Mid Century Rad Pad with Pool
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 76 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 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
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
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
Guest favourite
Home in Sarasota
The Golden Palms
6 bedrooms, 7 bathrooms
14–21 Sept
5.0 out of 5 average rating, 7 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 Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
15–20 Sept
4.93 out of 5 average rating, 44 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds, 2.5 bathrooms
26 Oct – 2 Nov
5.0 out of 5 average rating, 49 reviews
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
6–13 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Sarasota
Luxury Coastal Siesta Ocean Sandbar #1
5 bedrooms, 8 beds, 6 bathrooms
16–23 Sept