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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
4–9 Oct
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4.98 out of 5 average rating, 225 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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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
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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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 Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
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
1–6 Oct
5.0 out of 5 average rating, 17 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
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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Villa in Siesta Key
Villa Bella Mare
2 bedrooms, 3 beds, 2 bathrooms
1–8 Oct
4.94 out of 5 average rating, 18 reviews
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Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
1–8 Oct
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Top guest favourite
Apartment in Siesta Key
Beach Penthouse Balconies w/ Pool
3 bedrooms, 4 beds, 2 bathrooms
8–13 Dec
5.0 out of 5 average rating, 9 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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Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
28 Nov – 3 Dec
4.48 out of 5 average rating, 62 reviews
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Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 4 reviews
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Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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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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Guest favourite
Home in Siesta Key
Sea Escape - Located in Siesta Key Village!
1 bedroom, 2 beds, 1 bathroom
16–21 Nov
5.0 out of 5 average rating, 17 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