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Search results; Over 1,000 homes in Key West

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Top guest favourite
Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 327 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.72 out of 5 average rating, 25 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
Silver Palms Inn & Historic Homes, Classic Double.
1 bedroom, 2 queen beds, 1 bathroom
3–8 Oct
4.8 out of 5 average rating, 76 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
18–23 Sept
4.71 out of 5 average rating, 35 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
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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Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 41 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, 18 reviews
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Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Apartment in Key West
Hyatt Beach House-Quiet Key West Spot!
2 bedrooms, 3 beds, 2 bathrooms
4–11 Oct
5.0 out of 5 average rating, 22 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 82 reviews
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Top guest favourite
Home in Key West
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
1 bedroom, 1 bed, 1 bathroom
16–21 Nov
4.92 out of 5 average rating, 255 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
Apartment in Key West
Orchid Bay Condo + Pool • Old Town • Walk to Duval
1 bedroom, 2 beds, 1 bathroom
10–15 Oct
4.92 out of 5 average rating, 152 reviews
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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 245 reviews
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Featured hotel
Hotel in Key West
Seashell Motel, 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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Superhost
Boat in Key West
Houseboat in Key West
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
4.85 out of 5 average rating, 74 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