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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Condo de Paradise/Salt Water Pool/Boat Dock
2 bedrooms, 3 beds, 2 private bathrooms
10–17 Sept
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4.96 out of 5 average rating, 47 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
13–18 Sept
4.84 out of 5 average rating, 32 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds
13–18 Sept
4.81 out of 5 average rating, 72 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 21 reviews
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
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
17–22 Sept
4.91 out of 5 average rating, 561 reviews
Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Tiny home in Key West
Downtown Studio half block from Duval w parking
1 bed
26 Sept – 1 Oct
4.86 out of 5 average rating, 478 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
24–29 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds
10–15 Sept
4.93 out of 5 average rating, 87 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
Top guest favourite
Hotel room in Key West
The Sanchez House Room #2
1 bedroom, 1 queen bed
3–8 Oct
4.85 out of 5 average rating, 711 reviews
Featured hotel
Room in Key West
Queen Room
1 queen bed
15–20 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
10–15 Sept
4.88 out of 5 average rating, 177 reviews
Top guest favourite
Flat in Key West
Duval Balcony - Suite Mischief
1 bedroom, 1 king bed
28 Sept – 3 Oct
4.88 out of 5 average rating, 812 reviews
Guest favourite
Room in Key West
Mallory House Room #2
1 queen bed
10–15 Sept
4.91 out of 5 average rating, 442 reviews
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, 250 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds
10–15 Sept
4.9 out of 5 average rating, 245 reviews