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Search results; Over 1,000 homes in Siesta Key

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Guest favourite
Apartment in Siesta Key
Enchanting Coastal Ambiance & Breathtaking Sunsets
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
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4.89 out of 5 average rating, 106 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
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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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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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
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds
1–6 Oct
4.94 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds
5–10 Oct
4.93 out of 5 average rating, 43 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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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
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds
10–15 Oct
4.9 out of 5 average rating, 50 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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Top guest favourite
Apartment in Siesta Key
New listing - Beach Penthouse w/ Pool
3 bedrooms, 4 beds
8–13 Dec
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds
1–6 Oct
4.93 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Sarasota
Modern 4bd | Heated Pool | Hot Tub + Studio Suite!
4 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 23 reviews
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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