Vacation Homes in Key West
729 properties for Vacation Homes. Compare and book at the best price!
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Popular Vacation Homes in Key West
Key West, Lower Keys
9.8
Vacation home for 2 people, with pool and terrace as well as yard
Free cancellation
from $386 per night
Key West, Lower Keys
8.7
Vacation home for 4 people, with terrace and pool
Free cancellation
from $144 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with hot tub and terrace, with pets
from $546 per night
Key West, Lower Keys
9.3
Vacation home for 4 people, with terrace and pool as well as yard
Free cancellation
from $365 per night
Key West, Lower Keys
9.7
Vacation home for 6 people, with terrace and yard
Free cancellation
from $282 per night
Key West, Lower Keys
10.0
Vacation home for 4 people, with terrace
Free cancellation
from $622 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with hot tub
from $680 per night
Key West, Lower Keys
9.9
Vacation home for 4 people, with terrace and pool as well as hot tub
Free cancellation
from $320 per night
Key West, Lower Keys
9.5
Vacation home for 2 people, with terrace
Free cancellation
from $237 per night
Key West, Lower Keys
9.9
Vacation home for 2 people, with pool and balcony as well as yard
Free cancellation
from $717 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with terrace and yard
from $335 per night
Key West, Lower Keys
9.9
Vacation home for 4 people, with yard and balcony
Free cancellation
from $514 per night
Key West, Lower Keys
8.3
Vacation home for 4 people, with hot tub and terrace
Free cancellation
from $558 per night
Key West, Lower Keys
9.0
Vacation home for 2 people, with terrace
Free cancellation
from $200 per night
Key West, Lower Keys
9.0
Vacation home for 6 people, with terrace and hot tub
Free cancellation
from $596 per night
Key West, Lower Keys
9.6
Vacation home for 3 people, with balcony
from $314 per night
Key West, Lower Keys
Vacation home for 4 people, with terrace and yard
Free cancellation
from $216 per night
Key West, Lower Keys
9.9
Vacation home for 2 people, with pool and yard as well as terrace
Free cancellation
from $567 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with terrace
from $175 per night
Key West, Lower Keys
9.6
Vacation home for 3 people, with yard and balcony
from $340 per night
Key West, Lower Keys
9.2
Vacation home for 8 people, with terrace and yard
from $929 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with pool
from $358 per night
Key West, Lower Keys
9.6
Vacation home for 3 people, with terrace and hot tub
Free cancellation
from $620 per night
Key West, Lower Keys
9.8
Vacation home for 3 people, with terrace
Free cancellation
from $386 per night
Find Vacation Homes in Key West
Best Vacation Homes in Key West
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Key West, Lower Keys
Vacation Home • 1227 ft² • 2 Bedrooms
Key West, Lower Keys
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location Casa Bonita is your ideal home base for exploring the best of Old Town Key West! Nestled just steps from vibrant Duval Street, this spacious condo offers a perfect blend of comfort, style, and tropical charm. With lush gardens, a relaxing pool, and pleasant décor, this vacation rental promises an unforgettable escape in the heart of the island's action. The Ambiance: This serene condo comfortably accommodates up to six guests, featuring two private balconies that offer lush greenery and views of the lively area. In...
from $315 / night
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Key West, Lower Keys
Vacation Home • 4 Guests • 2 Bedrooms
Key West, Lower Keys
9.8
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation.As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring your privacy and creating a serene atmosphere.Inside, the cottage features an open living area and kitchen space, pe...
from $1,102 / night
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Key West, Lower Keys
Vacation Home • 721 ft² • 1 Bedroom
Key West, Lower Keys
9.3
Paradise SuiteOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street.Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh seafood restaurants and...
from $133 / night
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Other holiday ideas and property types in Key West that might be interesting
FAQs: Vacation Homes in Key West
When organizing a vacation to Key West, which services are the most important for travelers?
Judging by the information from Holidu, when travelers search for homes in Key West, most of the time they choose the following filters: pool (44%), balcony (12%), and a view (6%). Last year, most of the travelers selected at least one of these filters when finding the perfect home.
Which types of facilities are offered by the homes in Key West?
In regards to the amenities offered by Holidu, it seems that the homes in Key West benefit from everything that vacationers wish for! Here, the homes generally include a variety of facilities, the most popular being: air-conditioning (99%), internet (98%), and pool (70%)...Pretty cool!
What are the reviews like for the homes in Key West?
According to last year, less than 20% of the homes in Key West have a rating of 4.5 stars. It may therefore be not so easy for you to find a highly-rated home here.
Are the homes in Key West suitable for families with children?
Holidu's data reveals that 12% of homes in Key West are suitable for vacations with children, it will therefore be easy to find the ideal home for you and your children.
Are the homes in Key West suitable for travelers and their furry friends?
For sure! In Key West, 29% of the homes are pet-friendly, 17% also have a garden!
Do the homes in Key West mostly offer Wi-Fi?
Yes! According to Holidu, 98% of homes in Key West include internet connection. It is therefore no problem, you will be able to stay connected throughout your stay!
How much does it cost for homes in Key West?
Many homes in Key West are generally very expensive. Based off last year, 24% cost on average more than $500 a night.
Do the homes in Key West generally come equipped with a pool?
Definitely! According to Holidu, 70% of homes in Key West are equipped with a pool. It is the perfect destination for spending hot summer days by the pool! 46% even have a barbecue!
Are the homes in Key West suitable for stays with friends or better for a weekend break as a small group?
According to last year, 96% of homes are perfect for families with up to four travelers. Approximately 87% of the homes here are made up of at least two separate bedrooms. Key West is the perfect destination for a vacation as a small family!
For a luxurious vacation in Key West, are Homes a good idea?
Some homes are, but others aren't as luxurious. So if you are looking for that special accommodation, don't delay in making a reservation because only 70% have a pool, while 99% have air conditioning only 1% have a sauna.
Do the homes in Key West offer outdoor space to enjoy?
65% of homes have a balcony or terrace, and 19% have a view, but since it is not very common so availability can be limited. If this is a priority for you, you should start your research early, and use the filters to be sure to find the home of your dreams. However, if you like to have lunch or dinner outside, and especially if you like barbecues,46% of the homes are equipped with them.