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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
3 bedrooms, 5 beds, 3 private bathrooms
19–24 Sept
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5.0 out of 5 average rating, 12 reviews
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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, 9 reviews
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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, 14 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds
18–25 Sept
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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, 17 reviews
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Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds
18–23 Sept
5.0 out of 5 average rating, 11 reviews
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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, 49 reviews
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Top guest favourite
Bungalow in Sarasota
*Waterfront house with dock and heated pool
3 bedrooms, 4 beds
21–26 Sept
4.99 out of 5 average rating, 96 reviews
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Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds
26 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds
17–24 Sept
4.95 out of 5 average rating, 199 reviews
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Home in Siesta Key
Huge back yard w/heated pool & pet friendly house
3 bedrooms, 5 beds
27 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
26 Sept – 3 Oct
4.96 out of 5 average rating, 48 reviews
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Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds
6–13 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds
3–8 Oct
4.94 out of 5 average rating, 35 reviews
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Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
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Superhost
Home in Sarasota
Luxury Coastal Siesta Ocean Sandbar #1
5 bedrooms, 8 beds
17–24 Sept
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Top guest favourite
Home in Sarasota
Siesta Sands 1 Mile to Beach
3 bedrooms, 3 beds
17–24 Sept
4.95 out of 5 average rating, 19 reviews