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Search results; Over 1,000 homes in Key West

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Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
1 bedroom, 2 beds, 1 private bathroom
25–30 Sept
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4.86 out of 5 average rating, 394 reviews
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Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds
3–8 Oct
4.8 out of 5 average rating, 75 reviews
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Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds
17–22 Sept
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Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed
30 Oct – 4 Nov
4.95 out of 5 average rating, 19 reviews
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Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
2 bedrooms
25–30 Sept
4.8 out of 5 average rating, 25 reviews
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Featured hotel
Hotel in Key West
King city single room
1 bedroom, 1 king bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 25 reviews
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Featured hotel
Hotel in Key West
Havana king accessible
1 bedroom, 1 king bed
17–22 Sept
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Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
27 Sept – 2 Oct
4.91 out of 5 average rating, 562 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
17–22 Sept
4.71 out of 5 average rating, 35 reviews
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Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Home in Key West
Old Town Key West Escape - The “Eyebrow Saltbox”
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 16 reviews
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Top guest favourite
Hotel room in Key West
The Sanchez House Room #2
1 bedroom, 1 queen bed
3–8 Oct
4.85 out of 5 average rating, 711 reviews
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Top guest favourite
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
2 bedrooms, 1 king bed
17–22 Sept
4.98 out of 5 average rating, 565 reviews
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Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
2–7 Oct
4.83 out of 5 average rating, 29 reviews
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Superhost
Apartment in Key West
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
2 bedrooms, 3 beds
22–27 Sept
New place to stay
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Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
17–22 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
7–12 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Home in Key West
King Bed | Key West - Best Downtown Locations
1 bedroom, 2 beds
10–15 Oct
4.94 out of 5 average rating, 18 reviews