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Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 private bathroom
19–24 Sept
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4.89 out of 5 average rating, 185 reviews
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Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 84 reviews
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Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
4.96 out of 5 average rating, 55 reviews
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Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 116 reviews
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Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
21–28 Sept
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
3–10 Oct
New place to stay
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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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
20–25 Sept
4.89 out of 5 average rating, 104 reviews
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Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 10 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
19–24 Sept
4.88 out of 5 average rating, 132 reviews
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Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
4.83 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
8–15 Dec
4.95 out of 5 average rating, 20 reviews
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Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 reviews
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Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
25–30 Oct
4.95 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
20–27 Sept
5.0 out of 5 average rating, 81 reviews
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Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds, 2 bathrooms
28 Nov – 5 Dec
5.0 out of 5 average rating, 4 reviews
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Home in Marathon
Grand Retreat
4 bedrooms, 4 beds, 4 bathrooms
21–28 Sept
New place to stay
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Superhost
Home in Sugarloaf Key
Mi Azucar
2 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
4.81 out of 5 average rating, 175 reviews
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Superhost
Home in Marathon
Waterfront Home w/ Private Heated Pool & 60' Dock
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 3 Oct
New place to stay