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Search results; Over 1,000 homes in Siesta Key

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Apartment in Siesta Key
Siesta Key Beach (OHAB) Townhouse #1 beach
2 bedrooms, 2 beds, 2 private bathrooms
11–16 Oct
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4.85 out of 5 average rating, 122 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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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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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
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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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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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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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
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds
1–8 Oct
4.95 out of 5 average rating, 199 reviews
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Top guest favourite
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds
24–29 Oct
4.99 out of 5 average rating, 71 reviews
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Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed
15–20 Nov
5.0 out of 5 average rating, 4 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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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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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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Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
31 Dec – 5 Jan
5.0 out of 5 average rating, 14 reviews
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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
29 Nov – 4 Dec
5.0 out of 5 average rating, 16 reviews