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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Home in Siesta Key
Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!
4 bedrooms, 7 beds, 2 private bathrooms
16–21 Nov
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4.91 out of 5 average rating, 131 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, 11 reviews
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Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds
4–9 Oct
4.88 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 10 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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Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds
11–16 Oct
5.0 out of 5 average rating, 27 reviews
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Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 4 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 Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
16–21 Nov
5.0 out of 5 average rating, 15 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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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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Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
20–27 Oct
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Home in Sarasota
Casa Del Sol - 3 Bedrooms/2 Bathrooms (In-law Suite)
3 bedrooms, 3 beds
5–10 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds
5–10 Oct
4.93 out of 5 average rating, 44 reviews
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Superhost
Rooms in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
2 bedrooms, 2 queen beds
2–7 Oct
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Guest favourite
Home in Siesta Key
Bimini Breeze | Steps to Beach & Village
2 bedrooms, 4 beds
20–25 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Sarasota
Haven on Helene pool house.
3 bedrooms, 4 beds
1–6 Oct
4.97 out of 5 average rating, 73 reviews
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Guest favourite
Apartment in Siesta Key
Condo in popular Palm Bay Club
2 bedrooms, 5 beds
1–6 Oct
4.96 out of 5 average rating, 27 reviews
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Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds
1–8 Oct