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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
Siesta Dunes 1st Floor Beach Front Retreat
2 bedrooms, 4 beds, 2 private bathrooms
26 Sept – 3 Oct
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4.98 out of 5 average rating, 63 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
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 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
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
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
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 12 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
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
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 69 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
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
Top guest favourite
Flat in Sarasota
Siesta Sanctuary
2 bedrooms, 4 beds, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 43 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
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds, 5 bathrooms
14–21 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sarasota
Modern 4bd | Heated Pool | Hot Tub + Studio Suite!
4 bedrooms, 6 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 23 reviews