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 terrace and pool as well as yard
Free cancellation
from $465 per night
Key West, Lower Keys
8.7
Vacation home for 4 people, with pool and terrace
Free cancellation
from $193 per night
Key West, Lower Keys
9.7
Vacation home for 6 people, with terrace and yard
Free cancellation
from $287 per night
Key West, Lower Keys
9.4
Vacation home for 4 people, with yard and terrace as well as pool
Free cancellation
from $521 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with pool and hot tub as well as terrace, with pets
from $545 per night
Key West, Lower Keys
10.0
Vacation home for 4 people, with terrace and yard
Free cancellation
from $1,132 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with hot tub
from $798 per night
Key West, Lower Keys
Vacation home for 4 people, with balcony
Free cancellation
from $71 per night
Key West, Lower Keys
9.9
Vacation home for 4 people, with terrace and hot tub as well as pool
Free cancellation
from $546 per night
Key West, Lower Keys
9.9
Vacation home for 2 people, with balcony and yard as well as pool
Free cancellation
from $971 per night
Key West, Lower Keys
Vacation home for 4 people, with terrace and yard
Free cancellation
from $218 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with yard and terrace
from $451 per night
Key West, Lower Keys
8.3
Vacation home for 4 people, with terrace and hot tub
Free cancellation
from $557 per night
Key West, Lower Keys
9.1
Vacation home for 2 people, with terrace
Free cancellation
from $265 per night
Key West, Lower Keys
9.5
Vacation home for 2 people, with terrace
Free cancellation
from $266 per night
Key West, Lower Keys
9.9
Vacation home for 4 people, with balcony and yard
Free cancellation
from $538 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with terrace
from $199 per night
Key West, Lower Keys
9.9
Vacation home for 2 people, with terrace and pool as well as yard
Free cancellation
from $605 per night
Key West, Lower Keys
9.0
Vacation home for 6 people, with terrace and hot tub
Free cancellation
from $587 per night
Key West, Lower Keys
9.7
Vacation home for 3 people, with balcony
from $378 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with pool
from $461 per night
Key West, Lower Keys
9.2
Vacation home for 8 people, with yard and terrace
from $1,041 per night
Key West, Lower Keys
9.7
Vacation home for 3 people, with terrace and hot tub
Free cancellation
from $590 per night
Key West, Lower Keys
9.6
Vacation home for 3 people, with yard and balcony
from $381 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 • 3 Guests • 2 Bedrooms
Key West, Lower Keys
9.8
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected to traffic noises. Note two things:1. The price listed is for 2 guests only. There is an additional charge of $75/night for an additional guest. 2. The cottage is set back from the street but nearby at Hank's there is live music...luckily as of around 10.18.23 - their music is now set further...
from $482 / 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 $1,340 / 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 $124 / 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.