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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Apartment in Siesta Key
Comfy Siesta Key Condo
2 bedrooms, 4 beds, 2 private bathrooms
21–28 Oct
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4.85 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
1–6 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
28 Nov – 3 Dec
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
1–6 Oct
5.0 out of 5 average rating, 17 reviews
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Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds
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
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
3–8 Oct
4.94 out of 5 average rating, 35 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds
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
26 Oct – 2 Nov
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds
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
30 Oct – 4 Nov
4.48 out of 5 average rating, 62 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
29 Nov – 4 Dec
5.0 out of 5 average rating, 15 reviews
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Apartment in Sarasota
2 Bedroom and 2 Bathroom Gulf Front Condominium.
2 bedrooms, 3 beds
8–13 Oct
New place to stay
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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
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
20–25 Oct
New place to stay
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Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed
15–20 Nov
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Longboat Key
New Modern on Beach- Walk out 5 steps to Sand
1 bedroom, 2 beds
26 Nov – 1 Dec
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 397 reviews