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Search results; Over 1,000 homes in Key West

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Guest favourite
Apartment in Key West
Affordable Beachfront Luxury Condo Sleeps 6
2 bedrooms, 3 beds, 2 private bathrooms
20–25 Sept
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4.78 out of 5 average rating, 315 reviews
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Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.73 out of 5 average rating, 26 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
28 Sept – 3 Oct
4.81 out of 5 average rating, 79 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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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
20–25 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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Featured hotel
Hotel in Key West
Santa Maria Suites, Two bedroom bi-level pool vie.
2 bedrooms, 1 bathroom
20–25 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
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
21–26 Sept
4.88 out of 5 average rating, 177 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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Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 212 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
5–10 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
6–11 Nov
4.9 out of 5 average rating, 246 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
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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
25–30 Sept
4.99 out of 5 average rating, 88 reviews
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Superhost
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds, 1.5 bathrooms
26 Sept – 1 Oct
4.64 out of 5 average rating, 28 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, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 327 reviews
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Home in Key West
Walk to Duval St-Private Pool Oasis
3 bedrooms, 4 beds, 2 bathrooms
10–17 Nov
5.0 out of 5 average rating, 4 reviews