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Search results; Over 1,000 homes in Siesta Key

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Superhost
Apartment in Siesta Key
Crystal House on Siesta Key Beach
2 bedrooms, 6 beds, 1 private bathroom
5–10 Oct
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4.88 out of 5 average rating, 146 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, 11 reviews
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Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
1–6 Oct
5.0 out of 5 average rating, 17 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds
1–8 Oct
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Top guest favourite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Siesta Key
Bimini Breeze | Steps to Beach & Village
2 bedrooms, 4 beds
20–25 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 12 reviews
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Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
1–6 Oct
5.0 out of 5 average rating, 4 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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Villa in Siesta Key
Villa Bella Mare
2 bedrooms, 3 beds
1–8 Oct
4.94 out of 5 average rating, 18 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
Flat in Siesta Key
Gertrude’s Siesta | Pool, Jacuzzi, 1 Min to Beach!
2 bedrooms, 2 queen beds
12–17 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Sarasota
Sunshine Oasis, Heated Pool, 3BR, Near Siesta Key
3 bedrooms, 5 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Apartment in Sarasota
Casa Mar 35 2BR Gulfview Stay - Siesta Key Views
2 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 8 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
Bungalow in Sarasota
*Waterfront house with dock and heated pool
3 bedrooms, 4 beds
11–16 Oct
4.99 out of 5 average rating, 97 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
28 Nov – 3 Dec
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds
7–14 Oct
5.0 out of 5 average rating, 10 reviews