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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Flat in Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
1 bedroom, 2 beds, 1 private bathroom
15–20 Nov
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4.87 out of 5 average rating, 314 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
1–6 Oct
5.0 out of 5 average rating, 15 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, 10 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
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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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
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
5–10 Oct
5.0 out of 5 average rating, 12 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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Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds, 1 bathroom
17–24 Oct
5.0 out of 5 average rating, 12 reviews
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Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.48 out of 5 average rating, 62 reviews
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Top guest favourite
Flat in Siesta Key
Gertrude’s Siesta | Pool, Jacuzzi, 1 Min to Beach!
2 bedrooms, 2 queen beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 26 reviews
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Home in Sarasota
*BRAND NEW* heated pool, golf course views
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
New place to stay
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Guest favourite
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds, 6.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 11 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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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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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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Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 15 reviews