Find Vacation Rentals in Key West

Highlights Key West

  • Stunning sunsets
  • Family-friendly fun
  • Vibrant nightlife
  • Great food

Best Vacation Rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.
Key West, Lower Keys
Vacation Rental • 1894 ft² • 2 Bedrooms
(14 reviews)
Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting for gazing and relaxing. Luxurious amenities include large heated swimming pool and immaculate tennis court overlooking the ocean, plus a second free form heated swimming pool.A Miami South-Beach based architect designed the interior space of this property by setting a dramatic loft-like ladder t...
from $534 / night
Key West, Lower Keys
Vacation Rental • 872 ft² • 2 Bedrooms
(8 reviews)
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and all that Key West has to offer. The house is furnished in a coastal cottage décor. The living room has a sofa and seating area that overlooks a quiet deck, that is perfect for drinking your morning coffee. Kitchen is fully equipped with everything you could need, microwave, toaster and...
from $404 / night
Smathers Beach, Key West
Vacation Rental • 1399 ft² • 3 Bedrooms
(10 reviews)
If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace right across the street from the beach. Make your first order of the day to breathe in the fresh ocean breezes with a walk along the beach and fulfill the desire to dig those toes into warm white sand . . . for after all your front yard is the Atlantic Ocean. Your ‘back yard’ view is not bad eithe...
from $587 / night

Prices and availability

Current Vacation rental prices Key West

$763for 1 Apr - 8 Apr
$688 annual average
Average price per week

Current vacation rental availability Key West

3%for 1 Apr - 8 Apr
30% annual average
Percentage of available rentals

Vacation Rentals in Key West

Rental homes in Key West, Florida

From an oceanfront oasis of tranquility to a spacious villa reminiscent of a sea captain's mansion we have a delightful vacation home for you in Key West, Florida. Whether you want to be right on the waterfront or nestled in the hustle and bustle of the vibrant town you'll discover fully-equipped villas, bungalows, and apartments. Many have been tastefully renovated from old buildings and retain original and quaint period features.

All the comforts of home

Whether you're a couple looking for a romantic break or want a larger space for vacations with family and friends your ideal rental home is in Key West. All accommodation is fully furnished with comfortable bedrooms and spacious living and dining areas as well as all the kitchen appliances and equipment you need for cooking delicious meals. Many Key West vacation rentals also have their own gardens and swimming pools.


Key West - an island city

Key West is an island city in the {{Florida Keys}{ID}} and the most southerly point of continental {{America}{ID}}. It is joined to other islands and the mainland of {{Florida}{ID}} by the Overseas Highway. A vacation in Key West is perfect whether you want quiet, relaxed family fun or a vibrant nightlife.

Getting to Key West

Domestic flights can land at Key West Airport but most international visitors arrive through Miami International Airport.Rent a car and make the drive down the Florida coastline and across the Overseas Highway. This scenic route makes a good start to your vacation. Once you arrive in Key West be sure to take a tram ride tour of the city.

Mallory Square, Key West
Mallory Square, Key West


Key West for families

Key West is certainly a family-friendly destination with plenty to occupy children and the young at heart during the day. Although the beaches are not natural they are well-maintained with plenty of facilities and ideal for a lazy family day of making sandcastles, splashing around in the warm water and enjoying a picnic lunch. If you head to Higgs Beach then your children can also have fun at the Astro City Play Park.

Key West for fun lovers

Since the days of prohibition and speakeasies, Key West has had a reputation as a party town. Enjoy sunset carnivals any night of the week before heading to popular Irish bars and on to a jazz or blues club. To make sure you don't miss any highlights be sure to join an evening walking tour.

Key West for fishing

Head out into the Atlantic Ocean for some of the world's best sports fishing. Try your hand at catching and releasing blue and white marlin, sailfish, and swordfish or catch bonefish, tarpon, and snook in Florida Bay.

The top 5 things to do in Key West

1. Enjoy the sunset

Key West is one of the best places in the world to enjoy a spectacular sunset and the celebrations start in Mallory Square two hours before it's due. So grab your cocktail, sit back and watch the sun disappear in a blaze of color while being entertained by street artists.

2. Ernest Hemingway and Key West

Ernest Hemingway lived and wrote in Key West for a decade. Visit his house museum and look out for the descendants of the cats he bred that roam the garden. They all have extra toes!

3. McCoy Indigenous Park

The McCoy Indigenous Park is the home of the Florida Keys Wildlife Rescue Center. Animals from seabirds to raccoons are nursed back to health here and released into the wilds. At any one time, you can visit up to 100 animals being cared for by the center.

4. The Shipwreck Museum

This lively museum takes you into the world of wreckers and explores Key West's maritime history using actors, film, interactive displays, and real artifacts recovered from shipwrecks. Enjoy panoramic views of the city from the observation tower. Great fun for all the family.

5. Messing around on the water

A must-do activity in Key West is taking a trip on a glass-bottomed boat. You can wonder at North America's only living coral reef and shoals of colorful fish and if you're lucky you might see turtles or dolphins.

Useful information

The climate of Key West

Key West enjoys a mild, semi-tropical climate with cooler Winters and hotter Summers. The wettest months are from May to October. Although Key West is the driest city in Florida there are early morning showers on most days during the wet season. This is also when the risk of hurricanes is highest.

Dining and festivals

A Hemingway daiquiri, conch fritters, and Key Lime Pie are delicacies of Key West that must be sampled.

FAQs: Vacation Rentals in Key West

How much do the vacation rentals in Key West cost on average?

Based on last year, Key West had an average price of $548 per night, a relatively high one compared to the cities in the USA.

Which months allow you to save the most on vacation rentals?

If you would like to save as much as possible during your visit to Key West, pack your bags and travel there in September ($454 per night on average), June ($459), or August ($469), to find the lowest prices for the whole year.

In which months is it more expensive to rent a vacation rental in Key West?

Analyzing the data from last year, we found that costs per night for accommodation here are usually higher, on average, during the months of February ($691), March ($645), and January ($645).

Is it necessary to plan a trip to Key West well in advance?

It is better to plan ahead in Key West as only 13% of the accommodations are free throughout the year, following the data observed in the previous year.

When are more vacation rentals available?

June, May and August are, in order of highest to lowest, the months that have the largest number of properties free, with an average availability of 75%, 20%, and 12%. However, even during these months, when rental availability is the highest, the average is only 36%. So we highly recommend you always book a little in advance to make sure you get the rental of your dreams.

When are there fewer vacation rental options available in Key West?

The month with the highest average booked rental figures is April (only 1% of properties were available on average last year). Followed by March (2%), and then February (3%). During these three months, the availability is only 2%. It is therefore recommended to book early.

How many rentals are there in Key West?

In Key West we collaborate with 3 different providers to give you a choice of 420 properties, so you will not be short of options!

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