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Search results; Over 1,000 homes in Key West

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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
19–24 Sept
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4.9 out of 5 average rating, 245 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
17–22 Sept
4.71 out of 5 average rating, 35 reviews
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 562 reviews
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Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.8 out of 5 average rating, 75 reviews
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Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 140 reviews
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Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds, 3 bathrooms
29 Sept – 4 Oct
4.94 out of 5 average rating, 159 reviews
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Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 212 reviews
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Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
4.88 out of 5 average rating, 177 reviews
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Guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Downtown Near Duval
2 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
4.91 out of 5 average rating, 280 reviews
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Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 36 reviews
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Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 88 reviews
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Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
5–10 Oct
4.93 out of 5 average rating, 87 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 212 reviews
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Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
25–30 Sept
4.8 out of 5 average rating, 25 reviews
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Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.99 out of 5 average rating, 86 reviews
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Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 35 reviews