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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Key Wes't Best- Upgraded condo 5 mins to Smathers
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Jul
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4.89 out of 5 average rating, 106 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
4–9 Jul
4.87 out of 5 average rating, 175 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed
3–8 Jul
4.91 out of 5 average rating, 551 reviews
Featured hotel
Hotel in Key West
Accessible Classic King City/Balcony
1 bedroom, 1 king bed
27 Jul – 1 Aug
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed
23–28 Jul
4.92 out of 5 average rating, 353 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Awai's Floating Villa
2 bedrooms, 2 queen beds
1–6 Jul
4.93 out of 5 average rating, 82 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
5–10 Jul
4.89 out of 5 average rating, 139 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds
6–11 Jul
4.96 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Pet Friendly Near Duval St
4 bedrooms, 9 beds
5–10 Jul
4.89 out of 5 average rating, 220 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
1 bedroom, 1 queen bed
8–13 Aug
4.92 out of 5 average rating, 12 reviews
Guest favourite
Boat in Key West
Off Grid HouseBoat "Shanty Pineapple Key West"
1 bed
12–17 Jul
4.95 out of 5 average rating, 87 reviews
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed
6–11 Jul
5.0 out of 5 average rating, 24 reviews
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
6 bedrooms, 9 beds
11–16 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Sept
4.97 out of 5 average rating, 199 reviews
Hotel in Key West
Duval Street Stay + Free Breakfast, Pool & Bar
1 bedroom, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed
21–26 Jul
4.92 out of 5 average rating, 48 reviews
Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
1 bedroom, 2 beds
5–10 Jul
4.92 out of 5 average rating, 177 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds
26–31 Jul
4.91 out of 5 average rating, 208 reviews