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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Steps to Beach & Siesta Key Village-Village condo
2 bedrooms, 3 beds, 1 private bathroom
14–19 Sept
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4.93 out of 5 average rating, 242 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 8 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
13–18 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds
13–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Sarasota
St Armands Mid Century Rad Pad with Pool
3 bedrooms, 3 beds
14–19 Sept
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds
26 Oct – 2 Nov
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds
21–26 Sept
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds
14–19 Sept
4.96 out of 5 average rating, 24 reviews
Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Luxe
Home in Sarasota
Gulf View Penthouse | Gulf Views & Hot Tub
2 bedrooms, 3 beds
19–24 Sept
New place to stay
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key - 3 night min w/beach gear!
2 bedrooms, 4 beds
14–19 Nov
4.99 out of 5 average rating, 75 reviews
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds
28 Oct – 2 Nov
4.97 out of 5 average rating, 397 reviews
Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds
16–21 Sept
4.88 out of 5 average rating, 177 reviews
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds
14–19 Sept
4.93 out of 5 average rating, 44 reviews
Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds
26 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews