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Over 18,000 guest reviews for places to stay in Key West, with an average of 4.7 out of 5 stars.

300+ places to stay

Entire house
Enchanting seaside cottage w/private pool, off-street parking, & prime location
4 guests · 1 bedroom · 1 bed · 2 baths
Pool · Kitchen · Air conditioning
Entire house
New home w/ private pool & rooftop patio - ideal location & steps from beach!
8 guests · 4 bedrooms · 4 beds · 3.5 baths
Pool · Kitchen · Free parking · Air conditioning
Entire house
Dog-friendly home w/ private pool & space to lounge - walk to everything!
8 guests · 3 bedrooms · 4 beds · 3.5 baths
Pool · Kitchen · Air conditioning
Resort room
Rating 5.0 out of 53 reviews
Key West Getaway - 4 nights, 5 days
2 guests · 1 bedroom · 1 bed · 1 private bath
Pool · Free parking · Air conditioning
Entire house
Elegant, waterfront home w/ private pool and covered deck with ocean views
10 guests · 4 bedrooms · 7 beds · 3.5 baths
Pool · Kitchen · Free parking · Air conditioning
Entire house
Breezy Florida home with shared swimming pool, dog-friendly - walk to beach!
4 guests · 2 bedrooms · 2 beds · 1 bath
Pool · Kitchen · Free parking · Air conditioning
SUPERHOST
Entire house
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
8 guests · 3 bedrooms · 3 beds · 2 baths
Pool · Air conditioning
Entire condominium
Seaside escape with shared pool, hot tub, tennis courts, and more!
4 guests · 2 bedrooms · 2 beds · 2 baths
Pool · Kitchen · Free parking · Air conditioning
Entire house
Renovated home w/yard, porch & shared pool, one block from Duval Street -dogs OK
8 guests · 3 bedrooms · 4 beds · 2 baths
Pool · Kitchen · Free parking · Air conditioning
Entire house
Dog-friendly home w/ private pool - walk to parks, shopping, & the beach!
9 guests · 3 bedrooms · 5 beds · 3 baths
Pool · Kitchen · Free parking · Air conditioning
SUPERHOST
Resort room
Rating 5.0 out of 57 reviews
1BR Condo Banyan Tree, KeyWest #701
4 guests · 1 bedroom · 2 beds · 1 private bath
Pool · Kitchen · Air conditioning
SUPERHOST
Entire house
New to the Market! 4 Bed, 3 Bath-Old town w/ Pool!
8 guests · 4 bedrooms · 4 beds · 3 baths
Pool · Kitchen · Air conditioning
Entire guesthouse
Suite Dreams Monthly Studio Rental in Mid Town
4 guests · Studio · 2 beds · 1 bath
Pool · Kitchen · Air conditioning
Entire condominium
Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly!
6 guests · 2 bedrooms · 3 beds · 2.5 baths
Pool · Kitchen · Free parking · Air conditioning
Entire flat
Rating 4.65 out of 573 reviews
Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!
2 guests · Studio · 1 bed · 1 bath
Pool · Free parking · Air conditioning
Entire house
Stylish, inviting home w/private pool in heart of downtown - walk to everything!
6 guests · 3 bedrooms · 4 beds · 2.5 baths
Pool · Kitchen · Free parking · Air conditioning
Entire flat
Rating 4.78 out of 567 reviews
Luxurious Historic House With Pool in Old Town 2
4 guests · 1 bedroom · 1 bed · 1 bath
Pool · Kitchen · Free parking · Air conditioning
Entire condominium
Rating 4.60 out of 565 reviews
Lovely condo w/ pool & hot tub right nearby the beach. Family Friendly! Dogs OK!
6 guests · 2 bedrooms · 3 beds · 2 baths
Pool · Kitchen · Free parking · Air conditioning
1 18 of 300+ Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.