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Search results; Over 1,000 homes in Siesta Key

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Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 5 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
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, 2 bathrooms
3–8 Oct
4.94 out of 5 average rating, 35 reviews
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Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
6–13 Oct
5.0 out of 5 average rating, 3 reviews
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Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 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, 2.5 bathrooms
26 Oct – 2 Nov
5.0 out of 5 average rating, 49 reviews
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Apartment in Sarasota
2 Bedroom and 2 Bathroom Gulf Front Condominium.
2 bedrooms, 3 beds, 2 bathrooms
8–13 Oct
New place to stay
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Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 15 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Oct
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Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
4.99 out of 5 average rating, 70 reviews
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Top guest favourite
Flat in Longboat Key
New Modern on Beach- Walk out 5 steps to Sand
1 bedroom, 2 beds, 1 bathroom
26 Nov – 1 Dec
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 397 reviews
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Villa in Siesta Key
Villa Bella Mare
2 bedrooms, 3 beds, 2 bathrooms
1–8 Oct
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 8 reviews
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Superhost
Villa in Sarasota
Sunny Lido Beach Studio
1 bedroom, 1 bed, 1 bathroom
5–10 Oct
New place to stay
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Home in Siesta Key
Huge back yard w/heated pool & pet friendly house
3 bedrooms, 5 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 5 reviews