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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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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
18–23 Sept
4.71 out of 5 average rating, 35 reviews
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Guest favourite
Home in Key West
Cathouse Old Town Oasis Huge Heated Pool & Parking
4 bedrooms, 7 beds
22–27 Sept
4.98 out of 5 average rating, 80 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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Guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
9–14 Oct
4.9 out of 5 average rating, 157 reviews
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Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
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
19–24 Sept
4.88 out of 5 average rating, 177 reviews
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Guest favourite
Flat in Key West
Duval Balcony Spanky's Retreat
1 bedroom, 2 beds
26 Sept – 1 Oct
4.91 out of 5 average rating, 900 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
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds
3–8 Oct
4.99 out of 5 average rating, 140 reviews
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Guest favourite
Home in Key West
Near Key West | Bikes | Parking | Heated Pool
2 bedrooms, 3 beds
18–23 Sept
4.74 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 41 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
25–30 Sept
4.99 out of 5 average rating, 88 reviews
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Featured hotel
Hotel in Key West
Silver Palms Inn & Historic Homes, La Pensione In.
1 bedroom, 1 king bed
25–30 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds
5–10 Oct
4.93 out of 5 average rating, 87 reviews
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Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
25–30 Sept
5.0 out of 5 average rating, 3 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