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Search results; Over 1,000 homes in Key West

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Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds
1–6 Oct
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Featured hotel
Hotel in Key West
Seashell Motel, Queen Room
1 bedroom, 1 queen bed
9–14 Oct
5.0 out of 5 average rating, 21 reviews
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Featured hotel
Hotel in Key West
Havana king accessible
1 bedroom, 1 king bed
1–6 Oct
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
3–8 Oct
4.73 out of 5 average rating, 37 reviews
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Guest favourite
Flat in Key West
Casa Caribe 2bed2bath sleeps 6 beautiful decorated
2 bedrooms, 3 beds
9–14 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
14–19 Oct
4.91 out of 5 average rating, 562 reviews
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Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds
4–9 Oct
4.92 out of 5 average rating, 218 reviews
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Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
18–23 Oct
4.93 out of 5 average rating, 130 reviews
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Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds
25–30 Oct
4.89 out of 5 average rating, 123 reviews
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Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
9–14 Oct
4.9 out of 5 average rating, 158 reviews
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Guest favourite
Room in Key West
Mallory House Room #2
1 queen bed
1–6 Oct
4.91 out of 5 average rating, 443 reviews
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Guest favourite
Hotel room in Key West
The Sanchez House Room #1
1 bedroom, 1 queen bed
1–6 Oct
4.86 out of 5 average rating, 673 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds
1–6 Oct
4.95 out of 5 average rating, 37 reviews
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Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds
1–6 Oct
4.86 out of 5 average rating, 36 reviews
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Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 213 reviews
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Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 86 reviews