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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
Superhost
Home in Bradenton
Coastal Haven | Pool+Splash Pad+Theatre |Sleeps 18
5 bedrooms, 8 beds, 3 bathrooms
7–12 Sept
New place to stay
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
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
1–8 Sept
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
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
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
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
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
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
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 154 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
Guest favourite
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Sarasota
Luxury Coastal Siesta Ocean Sandbar #1
5 bedrooms, 8 beds, 6 bathrooms
1–8 Sept
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
Apartment in Siesta Key
Jamaica Royale 099 Nice Gulf side unit!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept