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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Bungalow in Siesta Key
Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
1 bedroom, 2 beds, 1 private bathroom
16–21 Sept
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4.98 out of 5 average rating, 47 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, 8 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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Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 178 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
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 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
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
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, 16 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
18–23 Sept
5.0 out of 5 average rating, 12 reviews
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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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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
17–24 Sept
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Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds, 2 bathrooms
10–17 Oct
4.97 out of 5 average rating, 63 reviews
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Top guest favourite
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Apartment in Siesta Key
Charming Siesta Key Condo Just Minutes from Beach
2 bedrooms, 3 beds, 2 bathrooms
20–26 Sept
4.96 out of 5 average rating, 84 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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Guest favourite
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds, 6.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 16 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