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Search results; Over 1,000 homes in Key West

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Top guest favourite
Boutique hotel in Key West
Mallory House Room #3
1 bedroom, 1 bed, 1 shared bathroom
20–25 Sept
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4.89 out of 5 average rating, 528 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed
19–24 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
20–25 Sept
4.71 out of 5 average rating, 35 reviews
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Featured hotel
Hotel in Key West
Silver Palms Inn & Historic Homes, Classic Double.
1 bedroom, 2 queen beds
3–8 Oct
4.81 out of 5 average rating, 77 reviews
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Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed
18–23 Sept
4.96 out of 5 average rating, 95 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
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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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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Superhost
Boat in Key West
Houseboat in Key West
1 bedroom, 1 bed
28 Sept – 3 Oct
4.85 out of 5 average rating, 74 reviews
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Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms
19–24 Sept
4.9 out of 5 average rating, 41 reviews
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Superhost
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds
26 Sept – 1 Oct
4.64 out of 5 average rating, 28 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds
3–10 Oct
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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Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
29 Sept – 4 Oct
4.94 out of 5 average rating, 159 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
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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Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed
4–9 Oct
4.92 out of 5 average rating, 362 reviews
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Guest favourite
Apartment in Key West
Orchid Bay Condo + Pool • Old Town • Walk to Duval
1 bedroom, 2 beds
10–15 Oct
4.92 out of 5 average rating, 152 reviews