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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
27 Sept – 2 Oct
,
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
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
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 15 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, 15 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
11–16 Sept
5.0 out of 5 average rating, 4 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
Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds
18–23 Sept
New place to stay
Luxe
Home in Sarasota
Gulf View Penthouse | Gulf Views & Hot Tub
2 bedrooms, 3 beds
19–24 Sept
New place to stay
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds
12–17 Sept
4.98 out of 5 average rating, 119 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
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds
19–24 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Sarasota
Luxury Sport Vacation Pool House-Downtown Sarasota
3 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 49 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, 48 reviews
Guest favourite
Home in Sarasota
New 8/8 bathroom beach house! Heated pool and spa!
8 bedrooms
11–18 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds
12–17 Sept
4.93 out of 5 average rating, 44 reviews
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds
11–18 Sept
5.0 out of 5 average rating, 3 reviews