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Search results; Over 1,000 homes in Key West

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Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
19–24 Sept
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4.9 out of 5 average rating, 245 reviews
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Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
16–21 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
2–7 Oct
4.83 out of 5 average rating, 29 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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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
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
17–22 Sept
4.88 out of 5 average rating, 177 reviews
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Superhost
Apartment in Key West
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
2 bedrooms, 3 beds
22–27 Sept
New place to stay
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Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds
22–27 Sept
4.9 out of 5 average rating, 251 reviews
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Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
21–26 Sept
4.9 out of 5 average rating, 156 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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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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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
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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Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 6 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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Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds
20–25 Sept
4.86 out of 5 average rating, 616 reviews
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Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds
13–18 Dec
4.96 out of 5 average rating, 47 reviews
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Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds
16–21 Sept
4.79 out of 5 average rating, 105 reviews