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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.91 out of 5 average rating, 561 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 32 reviews
Featured hotel
Room in Key West
Hearing Accessible Classic King City/Balcony
1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews
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, 158 reviews
Guest favourite
Home in Key West
Another Day in Paradise
3 bedrooms, 6 beds, 3 bathrooms
16–21 Nov
4.94 out of 5 average rating, 68 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Apartment in Key West
Waterfront Dock Pool Pet Friendly Near Duval St
4 bedrooms, 9 beds, 4 bathrooms
13–18 Sept
4.88 out of 5 average rating, 228 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Tiny home in Key West
Downtown Studio half block from Duval w parking
1 bed, 1 bathroom
26 Sept – 1 Oct
4.86 out of 5 average rating, 478 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Sept
4.93 out of 5 average rating, 87 reviews
Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 211 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 11 reviews
Featured hotel
Room in Key West
Queen Room
1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
10–15 Sept
4.88 out of 5 average rating, 177 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.81 out of 5 average rating, 63 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds, 4 bathrooms
22–27 Sept
4.9 out of 5 average rating, 250 reviews