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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, 12 reviews
Guest favourite
Home in Siesta Key
Siesta Key Home: Private Screened Pool
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 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
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 11 reviews
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
Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.9 out of 5 average rating, 48 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
1–8 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds, 2 bathrooms
17–24 Sept
4.97 out of 5 average rating, 62 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 Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.83 out of 5 average rating, 41 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Sarasota
Cozy Lido Key Studio Steps to Beach & Kayaking
1 bedroom, 1 king bed, 1 bathroom
6–11 Nov
4.98 out of 5 average rating, 62 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
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
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
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.94 out of 5 average rating, 34 reviews
Superhost
Home in Siesta Key
Endless Views | Panoramic View of Siesta Beach
3 bedrooms, 3 king beds, 3 bathrooms
27 Sept – 2 Oct
4.2 out of 5 average rating, 5 reviews
Guest favourite
Home in Siesta Key
Bimini Breeze | Steps to Beach & Village
2 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 9 reviews