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Search results; Over 1,000 homes in Key West

Superhost
Cottage in Key West
Colony Calypso - A quaint 1 Bedroom Cottage
1 bedroom, 2 beds, 1 shared bathroom
16–21 Sept
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4.65 out of 5 average rating, 17 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.74 out of 5 average rating, 34 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
Apartment in Key West
Parking & Shared Pool - Casa Key West
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.71 out of 5 average rating, 174 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, 159 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 561 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 177 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, 71 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
4–9 Oct
4.92 out of 5 average rating, 217 reviews
Featured hotel
Room in Key West
Queen Room
1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 22 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
4.85 out of 5 average rating, 99 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
11–16 Sept
4.93 out of 5 average rating, 87 reviews
Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.99 out of 5 average rating, 86 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
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.9 out of 5 average rating, 155 reviews