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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
1–6 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
28 Nov – 3 Dec
5.0 out of 5 average rating, 10 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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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
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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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
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds
17–24 Oct
5.0 out of 5 average rating, 12 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
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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Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
23–28 Oct
4.93 out of 5 average rating, 60 reviews
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Top guest favourite
Apartment in Siesta Key
New listing - Beach Penthouse w/ Pool
3 bedrooms, 4 beds
8–13 Dec
5.0 out of 5 average rating, 9 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, 13 reviews
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Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds
10–15 Oct
4.9 out of 5 average rating, 50 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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Superhost
Rooms in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
2 bedrooms, 2 queen beds
2–7 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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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