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Search results; Over 1,000 homes in Key West

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Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds, 2 private bathrooms
8–13 Oct
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4.87 out of 5 average rating, 307 reviews
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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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Featured hotel
Hotel in Key West
Seashell Motel, Queen Room
1 bedroom, 1 queen bed, 1 bathroom
9–14 Oct
5.0 out of 5 average rating, 21 reviews
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Featured hotel
Hotel in Key West
Silver Palms Inn & Historic Homes, Classic Double.
1 bedroom, 2 queen beds, 1 bathroom
16–21 Oct
4.81 out of 5 average rating, 86 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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Featured hotel
Hotel in Key West
Santa Maria Suites, Two bedroom bi-level pool vie.
2 bedrooms, 1 bathroom
31 Oct – 5 Nov
4.9 out of 5 average rating, 41 reviews
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Featured hotel
Hotel in Key West
Ella's Cottages - Key West Historic Inns, King ci.
1 bedroom, 1 king bed, 1 bathroom
5–10 Oct
4.96 out of 5 average rating, 28 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, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 19 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.73 out of 5 average rating, 37 reviews
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Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
4.85 out of 5 average rating, 112 reviews
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Top guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
4.83 out of 5 average rating, 30 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
11–16 Oct
4.88 out of 5 average rating, 177 reviews
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Guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds, 3 bathrooms
1–6 May
5.0 out of 5 average rating, 24 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
1–6 Oct
4.99 out of 5 average rating, 88 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, 141 reviews
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Hotel in Key West
Duval Street Stay + Free Breakfast, Beach & Pool
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Key West
Another Day in Paradise
3 bedrooms, 6 beds, 3 bathrooms
16–21 Nov
4.94 out of 5 average rating, 72 reviews