Vacation Homes in Florida Keys
3,253 properties for Vacation Homes. Compare and book at the best price!
Find offers
Popular Vacation Homes in Florida Keys
Duck Key, Monroe County
Vacation home for 4 people, with pool and balcony
Free cancellation
from $618 per night
Key West, Lower Keys
9.4
Vacation home for 2 people, with yard and terrace as well as pool
Free cancellation
from $372 per night
Cudjoe Key, Lower Keys
7.9
Vacation home for 4 people, with terrace
Free cancellation
from $223 per night
Key West, Lower Keys
8.7
Vacation home for 4 people, with terrace and pool
Free cancellation
from $157 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with yard and terrace
from $440 per night
Key West, Lower Keys
Vacation home for 6 people, with terrace and yard
Free cancellation
from $556 per night
Key West, Lower Keys
9.9
Vacation home for 2 people, with terrace and pool
Free cancellation
from $436 per night
Islamorada, Monroe County
10.0
Vacation home for 4 people, with pool and hot tub
Free cancellation
from $470 per night
Key West, Lower Keys
9.4
Vacation home for 2 people, with terrace
Free cancellation
from $478 per night
Key West, Lower Keys
9.7
Vacation home for 6 people, with yard and terrace
Free cancellation
from $276 per night
Key West, Lower Keys
Vacation home for 6 people, with pool
Free cancellation
from $550 per night
Little Torch Key, Lower Keys
8.7
Vacation home for 4 people, with yard and terrace
Free cancellation
from $418 per night
Cudjoe Key, Lower Keys
9.0
Vacation home for 4 people, with pool and terrace
Free cancellation
from $373 per night
Key West, Lower Keys
Vacation home for 6 people, with terrace
Free cancellation
from $494 per night
Monroe County
8.6
Vacation home for 2 people
Free cancellation
from $249 per night
Sugarloaf Key, Lower Keys
Vacation home for 8 people, with yard and balcony, with pets
Free cancellation
from $3,266 per night
Marathon, Monroe County
8.8
Vacation home for 4 people, with pool and balcony
Free cancellation
from $301 per night
Key West, Lower Keys
10.0
Vacation home for 6 people, with terrace and pool as well as yard, with pets
Free cancellation
from $261 per night
Marathon, Monroe County
9.6
Vacation home for 4 people, with pool and balcony
Free cancellation
from $290 per night
Marathon, Monroe County
10.0
Vacation home for 2 people
Free cancellation
from $332 per night
Marathon, Monroe County
9.6
Vacation home for 2 people, with terrace
Free cancellation
from $151 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with pool and terrace, with pets
Free cancellation
from $197 per night
Key West, Lower Keys
10.0
Vacation home for 2 people, with terrace and yard
Free cancellation
from $162 per night
Key West, Lower Keys
9.6
Vacation home for 2 people, with hot tub and terrace, with pets
from $516 per night
Find Vacation Homes in Florida Keys
Best Vacation Homes in Florida Keys
Guests agree: these stays are highly rated for location, cleanliness, and more.
more...
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 $148 / night
View offer
more...
Monroe County
Vacation Home • 969 ft² • 2 Bedrooms
Monroe County
9.7
Welcome to Tranquility Cottage, a beautifully appointed, well maintained, and updated 2BR/2B half-duplex on 7th Street in Key Colony Beach. Located on the widest canal in Key Colony Beach and opposite Sadowski Causeway you will be in walking distance of local restaurants, Sunset Beach, Fishing and Dive Charter Boats, and the Cabana Club. The house also has a Tiki Hut that is quite spacious and fabulous for relaxing and getting some shade.Four (4) person occupancy. 7 – Night minimum stay. Sorry, NO SMOKING (INCLUDING E-CIGARETTES) or PETS.Bedding includes a Queen bed in the Master Bedroom, 2...
from $252 / night
View offer
more...
Key West, Lower Keys
Vacation Home • 495 ft² • 1 Bedroom
Key West, Lower Keys
9.0
NEWLY REDECORATED AS OF APRIL 15. 2025 all dark natural wood walls and cabinets gone instead painted off-white color throughout. Really lightens up the place.Orange walls are gone as well. Instead, painted pastel color and in the bathroom. Cabinet under bathroom sink is gone. Just imagine new pedestal sunk opening up the bathroom. GREAT LOCATION Close to beach and All!REASONABLE RATES. W. KITCHEN AND PATIOCome splash in the surf. Come soak up the heat of the Sun. Come feel salt water mist on your skin as you take a sunset sail! Come listen to the beat of the reggae drums. Come feel the loos...
from $186 / night
View offer
Other holiday ideas and property types in Florida Keys that might be interesting
Vacation Homes in Florida Keys: Most popular destinations
FAQs: Vacation Homes in Florida Keys
Which facilities are the most searched for by travelers for their stay in the Florida Keys?
When looking at the data from Holidu, when travelers search for homes in the Florida Keys, often they choose the following filters: pool (34%), internet (15%), and a air-conditioning (12%). Last year, the majority of people searching selected at least one of these options when finding the perfect home.
Which types of amenities can you typically find at the homes in the Florida Keys?
In regards to the amenities available on Holidu, it appears that the homes in the Florida Keys offer everything that vacationers search for! Here, the homes generally include a variety of facilities, the most popular being: air-conditioning (97%), internet (96%), and balcony (69%)...Sounds tempting?
How do travelers usually rate homes in the Florida Keys?
According to last year, most of the homes in the Florida Keys receive a rating of less than 4.5 stars. It may therefore be not so easy for you to find a highly-rated home here.
Are the homes in the Florida Keys suitable for family vacations?
According to the Holidu database, 25% of homes in the Florida Keys are suitable for families with children, it will therefore not be difficult to find the perfect home for you and your family.
Are the homes in the Florida Keys suitable for travelers and their furry friends?
For sure! In the Florida Keys, 32% of the homes give you the opportunity to bring along your furry best friend, 23% even have a garden!
Do the homes in the Florida Keys often have Wi-Fi?
Yes! According to Holidu's data, 96% of homes in the Florida Keys include internet connection. It is therefore no problem, you will be able to access your emails and favorite social media sites during your stay!
How much does it usually cost for homes in the Florida Keys?
Many homes in the Florida Keys are, in general, fairly expensive. According to Holidu, 21% are at more than $500 per night.
Do the homes in the Florida Keys usually come equipped with a fireplace or a pool?
Good news! According to Holidu's data, 65% of homes in the Florida Keys have a pool. Perfect for spending your summer vacation by the pool! 64% even have a barbecue!
Are the homes in the Florida Keys suitable for vacations with a big group or better for a vacation as a couple?
According to last year, 98% of homes welcome small groups of up to four guests. Approximately 92% of the homes here are made up of at least two separate bedrooms. This is the perfect destination for taking your small family on vacation!
Are Homes in the Florida Keys the best option for a luxurious stay?
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 65% have a pool, while 97% have air conditioning only 1% have a sauna. However, if it's space you're looking for, 98% of the homes can accommodate four or more adults, and 23% have a garden.
At the homes in the Florida Keys are you able to have a beautiful view and spend time outside?
69% of homes have a balcony or terrace, and 43% have a view, but since it is not very common so availability can be limited. If this is important to you, you should anticipate a bit more time for research, and use the filters to be sure to find the home of your dreams. However, 23% of homes in the Florida Keys have gardens, where you can enjoy the outdoors. If you like to have lunch or dinner outside, and especially if you like barbecues, 64% of the homes have them.