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Search results; Over 1,000 homes

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Superhost
Home in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock
2 bedrooms, 4 beds, 1 private bathroom
15–20 Oct
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4.89 out of 5 average rating, 185 reviews
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Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp
3 bedrooms, 6 beds, 1 bathroom
12–17 Oct
4.93 out of 5 average rating, 127 reviews
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Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool
4 bedrooms, 5 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 17 reviews
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Featured hotel
Hotel in Marathon
Coconut Cay Resort & Marina, Canal view 2 queen i.
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
1–8 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
4.83 out of 5 average rating, 12 reviews
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
New place to stay
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Featured hotel
Hotel in Key West
Havana Cabana at Key West, Havana 2 queens
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
5.0 out of 5 average rating, 81 reviews
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Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
4.88 out of 5 average rating, 133 reviews
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Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.83 out of 5 average rating, 112 reviews
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Featured hotel
Hotel in Key West
Porch swing island room
1 bedroom, 1 double bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 6 reviews
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Featured hotel
Hotel in Key West
Havana Cabana at Key West, Havana king accessible
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
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Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
6–11 Oct
4.95 out of 5 average rating, 183 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 621 reviews
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Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.86 out of 5 average rating, 620 reviews
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Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
4.89 out of 5 average rating, 104 reviews