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Search results; Over 1,000 homes in Siesta Key

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Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 5 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 170 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
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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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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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
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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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
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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Top guest favourite
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed
13–18 Oct
5.0 out of 5 average rating, 9 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, 61 reviews
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Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds
28 Oct – 2 Nov
4.97 out of 5 average rating, 397 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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Townhouse in Siesta Key
Midnight Cove II 220D - Peaceful Bayside Vacation!
3 bedrooms, 4 beds
17–24 Oct
5.0 out of 5 average rating, 4 reviews
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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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Guest favourite
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds
25–30 Oct
5.0 out of 5 average rating, 11 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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Top guest favourite
Home in Siesta Key
Stroll to the Sea, Steps to the Village, Boat dock
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
31 Dec – 5 Jan
5.0 out of 5 average rating, 13 reviews