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Search results; Over 1,000 homes in Key West

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Guest favourite
Cottage in Key West
Pete's West Cottage steps from Duval
2 bedrooms, 2 beds, 1 shared bathroom
4–9 Oct
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4.96 out of 5 average rating, 46 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed
17–22 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
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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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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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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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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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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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds
19–24 Sept
4.9 out of 5 average rating, 245 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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Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 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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Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.93 out of 5 average rating, 56 reviews
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Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed
17–22 Sept
4.96 out of 5 average rating, 95 reviews
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Top guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed
4–9 Oct
4.93 out of 5 average rating, 98 reviews
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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
25–30 Oct
4.97 out of 5 average rating, 327 reviews
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Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 36 reviews
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Top guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 13 reviews