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Search results; Over 1,000 homes in Siesta Key

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Top guest favourite
Flat in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
2 bedrooms, 4 beds, 2 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 224 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, 14 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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Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 397 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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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 Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Siesta Key
Huge back yard w/heated pool & pet friendly house
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 4 Oct
5.0 out of 5 average rating, 4 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
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 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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Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 3 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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Townhouse in Siesta Key
3 bdrm 4 bath Beachhouse
3 bedrooms, 4 beds, 3.5 bathrooms
24 Sept – 1 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
17–24 Sept
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Guest favourite
Apartment in Siesta Key
Beautiful 3rd Floor Condo facing the Gulf of Mex
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 6 reviews