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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
Siesta Key Condo. Checkout our great rates!
2 bedrooms, 4 beds, 1.5 private bathrooms
24–31 Oct
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4.96 out of 5 average rating, 140 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, 11 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
13–19 Sept
New place to stay
Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 5 beds, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 169 reviews
Top guest favourite
Home in Sarasota
Modern 4bd | Heated Pool | Hot Tub + Studio Suite!
4 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 22 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, 48 reviews
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
1–8 Sept
Top guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Bungalow in Sarasota
*Waterfront house with dock and heated pool
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 96 reviews
Home in Sarasota
Periwinkle House
5 bedrooms, 6 beds, 3.5 bathrooms
1–7 Sept
New place to stay
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sarasota
Modern Home Heated Pool near Siesta & Downtown
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 46 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, 14 reviews
Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.48 out of 5 average rating, 61 reviews