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Search results; Over 1,000 homes in Siesta Key

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Top guest favourite
Flat in Siesta Key
Siesta Premier Location - The 'Calm of Siesta'
2 bedrooms, 2 beds, 2 private bathrooms
20–27 Oct
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4.94 out of 5 average rating, 143 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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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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Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds
18–23 Sept
4.88 out of 5 average rating, 178 reviews
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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
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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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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Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds
18–23 Sept
5.0 out of 5 average rating, 3 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
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed
28 Sept – 3 Oct
5.0 out of 5 average rating, 11 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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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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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
Home in Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds
10–17 Oct
4.97 out of 5 average rating, 64 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
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds
5–10 Oct
4.84 out of 5 average rating, 43 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