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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Apartment in Siesta Key
Beach Retreat - Jamaica Royale Unit #52
1 bedroom, 1 bed, 1 private bathroom
31 Oct – 5 Nov
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4.86 out of 5 average rating, 138 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, 11 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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Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.88 out of 5 average rating, 179 reviews
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Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 4 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
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 10 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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Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
1–8 Oct
4.95 out of 5 average rating, 199 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, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
20–27 Oct
4.96 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Sarasota
Modern 1BR Near Siesta Key + Private Parking
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 278 reviews
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Guest favourite
Home in Siesta Key
Bimini Breeze | Steps to Beach & Village
2 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
5–10 Oct
4.93 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 39 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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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