Vacation Homes in Key West
729 properties for Vacation Homes. Compare and book at the best price!
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- Vacation Homes Key West
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Popular Vacation Homes in Key West
Key West, Lower Keys
8.8
Vacation home for 10 people, with terrace and yard, with pets
Free cancellation
from $897 per night
Key West, Lower Keys
9.7
Vacation home for 8 people, with yard and balcony, kid friendly
Free cancellation
from $693 per night
Key West, Lower Keys
9.1
Vacation home for 10 people, with terrace
Free cancellation
from $1,040 per night
Key West, Lower Keys
9.8
Vacation home for 6 people, with yard and terrace as well as pool, with pets
Free cancellation
from $282 per night
Key West, Lower Keys
Vacation home for 12 people, with terrace and yard
Free cancellation
from $1,220 per night
Key West, Lower Keys
Vacation home for 6 people, with terrace and yard
Free cancellation
from $748 per night
Key West, Lower Keys
Vacation home for 8 people, with yard and pool as well as balcony, kid friendly
Free cancellation
from $591 per night
Key West, Lower Keys
Vacation home for 6 people, with terrace
Free cancellation
from $736 per night
Key West, Lower Keys
Vacation home for 19 people, with yard and terrace, with pets
Free cancellation
from $2,391 per night
Key West, Lower Keys
Vacation home for 12 people, with yard and balcony, kid friendly
Free cancellation
from $2,422 per night
Key West, Lower Keys
Vacation home for 16 people, with yard and balcony, kid friendly
Free cancellation
from $1,817 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
Vacation home for 6 people, with balcony and yard, kid friendly
Free cancellation
from $360 per night
Key West, Lower Keys
9.7
Vacation home for 6 people, with yard and terrace
Free cancellation
from $397 per night
Key West, Lower Keys
8.7
Vacation home for 4 people, with terrace and pool
Free cancellation
from $186 per night
Key West, Lower Keys
10.0
Vacation home for 6 people, with yard and terrace as well as hot tub
Free cancellation
from $472 per night
Key West, Lower Keys
9.4
Vacation home for 4 people, with pool and terrace as well as yard
Free cancellation
from $608 per night
Key West, Lower Keys
9.3
Vacation home for 6 people, with yard and terrace, with pets
Free cancellation
from $271 per night
Key West, Lower Keys
9.8
Vacation home for 12 people, with yard
Free cancellation
from $2,275 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with pool and terrace as well as hot tub, with pets
from $698 per night
Key West, Lower Keys
9.7
Vacation home for 2 people, with yard and terrace
from $527 per night
Key West, Lower Keys
9.7
Vacation home for 20 people, with hot tub and yard as well as balcony
from $3,202 per night
Key West, Lower Keys
10.0
Vacation home for 8 people, with hot tub and yard as well as balcony
Free cancellation
from $4,651 per night
Key West, Lower Keys
9.0
Vacation home for 6 people, with hot tub and terrace
Free cancellation
from $691 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 • 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 $1,458 / night
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Key West, Lower Keys
Vacation Home • 1195 ft² • 2 Bedrooms
Key West, Lower Keys
9.2
Welcome to Your Tropical Escape at Duval Square Discover the perfect Key West getaway in this beautiful 2-bedroom, 2.5-bathroom retreat located in the exclusive gated community of Duval Square. Nestled on upper Duval Street—just steps from restaurants, cafés, and island conveniences - this property offers the ideal blend of privacy, luxury, and unbeatable location.Property Highlights:~ Spacious & Stylish LivingRelax in the bright, comfortable living room featuring a sofa bed, convenient powder room, and easy access to your private balcony.~ Master Bedroom SuiteUnwind in the serene maste...
from $697 / night
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Key West, Lower Keys
Vacation Home • 958 ft² • 2 Bedrooms
Key West, Lower Keys
9.7
PLEASE BE AWARE...We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nights if your arrival is 12/22 or before. PICTURE PERFECT…Swaying palms and a picturesque white picket fence outline this tropical retreat luring you in to your escape from reality. Unbeatable location with all the desired amenities, this home is perfect for your island destination. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEDETAILS AND AMENITIES…Enjoy an open floor plan on the lower level beginning with a fully equipped kitchen showcasing stainless steel appliances and a...
from $517 / 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.