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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Apartment in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
2 bedrooms, 3 beds, 2 private bathrooms
3–10 Oct
,
4.97 out of 5 average rating, 76 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, 9 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
26 Sept – 1 Oct
5.0 out of 5 average rating, 15 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
19–24 Sept
4.88 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 3 Oct
4.96 out of 5 average rating, 48 reviews
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Superhost
Apartment in Siesta Key
100% Private Home and Pool, just 500ft to Beach
6 bedrooms, 10 beds, 4 bathrooms
8–13 Dec
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, 2 bathrooms
3–8 Oct
4.94 out of 5 average rating, 35 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
20–25 Sept
5.0 out of 5 average rating, 17 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
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 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, 25 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
19–26 Sept
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Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 156 reviews
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Top guest favourite
Bungalow in Sarasota
*Waterfront house with dock and heated pool
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 96 reviews
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Home in Sarasota
*BRAND NEW* heated pool, on golf course
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
New place to stay
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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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Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.93 out of 5 average rating, 44 reviews
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Guest favourite
Home in Sarasota
Casa Del Sol - 3 Bedrooms/2 Bathrooms (In-law Suite)
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 16 reviews