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Search results; Over 1,000 homes in Key West

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Top guest favourite
Boat in Key West
A Great Escape! Private 2 Bed Rm Beautiful Marina
2 bedrooms, 2 beds, 1 private bathroom
18–23 Sept
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4.83 out of 5 average rating, 185 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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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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Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 41 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
18–23 Sept
4.88 out of 5 average rating, 177 reviews
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Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 22 reviews
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Superhost
Apartment in Key West
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
New place to stay
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Guest favourite
Home in Key West
Cathouse Old Town Oasis Huge Heated Pool & Parking
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Sept
4.98 out of 5 average rating, 80 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, 29 reviews
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Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 6 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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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 10 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
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
The Perch on Duval- Hip & Modern Duval Suite
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 118 reviews
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Guest favourite
Apartment in Key West
Caribbean Conch 5 Minutes to Smathers Beach & 10 m
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.72 out of 5 average rating, 69 reviews
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Guest favourite
Home in Key West
Near Key West | Bikes | Parking | Heated Pool
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
4.74 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds, 2 bathrooms
13–18 Dec
4.96 out of 5 average rating, 47 reviews