Old Town Key West vacation rentals

We found 1,559 vacation rentals — enter your dates for availability

Select from 700 houses, 278 condos, and other vacation rentals to find the perfect place for your stay in Old Town Key West. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Frequently asked questions

What is the most popular type of vacation rental accommodation in Old Town Key West?
Condos are the most popular style of vacation rental in Old Town Key West, according to our data. Even if you’ve got something a little different in mind, Vrbo has vacation homes in all shapes and sizes. Browse our many options to find your perfect pad.
How much does it cost to rent a vacation rental in Old Town Key West?
The average price for a vacation home in Old Town Key West is determined by several factors, including season, length of stay and property type. Whether you’re thinking about a sprawling villa with a pool or an apartment ideal for just you and the kids, just enter your travel dates to view stays with great value.
How much does it cost to rent a beach house in Old Town Key West?
Prices for beach houses in Old Town Key West vary depending on the style and size of the property and time of year you’re traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use the filters to refine your search by ratings, amenities, nearby activities and more.
Are there pet-friendly vacation rentals in Old Town Key West?
Pack a travel bag for the pooch in your life because Old Town Key West has 1,320 vacation homes that roll out the welcome mat to doggie guests. Let your four-legged friend join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our “Pets allowed” filter box.
Can I rent a house with a pool in Old Town Key West?
Add a new level of fun to your getaway by booking your family into one of the 1,055 houses with a private pool in Old Town Key West. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days splishing and splashing in a swimming pool that’s all your own.
What are popular rental amenities in Old Town Key West?
A garden, a firepit and an ocean view rank as the most popular rental amenities in Old Town Key West. Whether you plan to travel as a party of one, with your spouse or a bunch of friends, Vrbo can help you find a vacation home that matches your tastes with all the extras you’re looking for.
Are there large group vacation rentals in Old Town Key West?
You can pick from 121 vacation properties in Old Town Key West that can host a group of 10 or more guests. Whether you’re planning a trip with extended family or a special event like a birthday party, there’s plenty of space to get your loved ones together under the same roof.
Are there vacation rentals in Old Town Key West that welcome kids?
Bring the entire group together for a fun-filled adventure in Old Town Key West at one of our 1,303 family-friendly vacation rentals. A lot of these stays provide conveniences that are great for getaways with youngsters, such as laundry facilities, living rooms and patios. Simply check the “Properties good for families” filter and select your favorite.
What are the top attractions for families in Old Town Key West?
Keeping the kids happy during your stay in Old Town Key West is simple with these exciting family-friendly attractions:

  • Clarence S. Higgs Memorial Beach Park
  • South Beach
  • Simonton Beach

Are there one-bedroom vacation rentals in Old Town Key West?
Yes, you can pick from 409 one-bedroom rentals in Old Town Key West. Whether you’re looking for an apartment or a condo, Vrbo’s one-bedroom rentals are ideal if you don’t need lots of space. One of the main perks of having your own pad? You won’t have to share your vacation with strangers.
Can I find two-bedroom vacation rentals in Old Town Key West?
Gather your loved ones and enjoy peace, privacy and comfort in one of the 507 two-bedroom vacation rentals Old Town Key West has to offer.
Are there vacation rentals with WiFi in Old Town Key West?
You’ll find 566 vacation rentals with WiFi in Old Town Key West. If you’d like to disconnect from daily life while on vacation, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Old Town Key West?
You can choose from 1,282 vacation rentals with air conditioning in Old Town Key West offering that gentle, cool breeze and extra comfort level. Just enter your preferred travel dates and then use our handy filters to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in Old Town Key West?
The minimum required age is typically 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your preferred Old Town Key West vacation home before booking.
How long can I rent a vacation rental in Old Town Key West for?
The length of time you can book a vacation rental in Old Town Key West is down to the property. Simply enter your preferred travel dates to look at a list of options offering extended stays. With plenty of amenities such as washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to find someplace just right to call your home away from home in Old Town Key West.
Does Vrbo offer discounts for vacation homes in Old Town Key West?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some great deals and discounts on Vrbo. From weekend retreats to extended getaways, we’ve got you covered for your next Old Town Key West escape.

Explore destinations around Old Town Key West

More Vacation Rentals ideas

Palm Springs Vacation Rentals
Standard Link for Palm Springs
Ocean City Vacation Rentals
Standard Link for Ocean City
WaterSound Beach Vacation Rentals
Standard Link for WaterSound Beach
Seagrove Beach Vacation Rentals
Standard Link for Seagrove Beach
Charleston Vacation Rentals
Standard Link for Charleston
Inlet Beach Vacation Rentals
Standard Link for Inlet Beach
Crescent Beach Vacation Rentals
Standard Link for Crescent Beach
Truman Annex Vacation Rentals
Standard Link for Truman Annex
Watercolor Vacation Rentals
Standard Link for Watercolor
Mid Beach Vacation Rentals
Standard Link for Mid Beach
Plantation Vacation Rentals
Standard Link for Plantation
Crystal Beach Vacation Rentals
Standard Link for Crystal Beach
Steamboat Springs Vacation Rentals
Standard Link for Steamboat Springs
Kailua-Kona Vacation Rentals
Standard Link for Kailua-Kona
Baytowne Wharf Vacation Rentals
Standard Link for Baytowne Wharf
Pensacola Beach Vacation Rentals
Standard Link for Pensacola Beach
South Island Vacation Rentals
Standard Link for South Island
Myrtle Beach Vacation Rentals
Standard Link for Myrtle Beach
Destin Vacation Rentals
Standard Link for Destin
Key West Vacation Rentals
Standard Link for Key West
Butler Beach Vacation Rentals
Standard Link for Butler Beach
Blue Mountain Beach Vacation Rentals
Standard Link for Blue Mountain Beach
Orange Beach Vacation Rentals
Standard Link for Orange Beach
Seacrest Beach Vacation Rentals
Standard Link for Seacrest Beach
Rosemary Beach Vacation Rentals
Standard Link for Rosemary Beach
South Beach Vacation Rentals
Standard Link for South Beach
Port Aransas Vacation Rentals
Standard Link for Port Aransas
Seaside Vacation Rentals
Standard Link for Seaside
Holiday Isle Vacation Rentals
Standard Link for Holiday Isle
Downtown Miami Vacation Rentals
Standard Link for Downtown Miami