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Search results; Over 1,000 homes in Siesta Key

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Top guest favourite
Apartment in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 bedroom, 1 bed, 1 private bathroom
30 Sept – 5 Oct
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5.0 out of 5 average rating, 172 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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Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 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 Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
20–27 Sept
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Townhouse in Siesta Key
3 bdrm 4 bath Beachhouse
3 bedrooms, 4 beds, 3.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 4 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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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
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds, 2 bathrooms
8–13 Dec
5.0 out of 5 average rating, 17 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
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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Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
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, 2 bathrooms
10–15 Oct
4.9 out of 5 average rating, 50 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
21–26 Sept
5.0 out of 5 average rating, 12 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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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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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
Home in Sarasota
Sunshine Oasis, Heated Pool, 3BR, Near Siesta Key
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 6 reviews