Old Town Key West Vacation Rentals

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Make Old Town Key West your next getaway—choose from 107 great vacation rentals

There’s just something special about staying in Old Town during your Key West vacation—and with our Old Key West rentals, you can do just that. This historic part of the Florida Keys includes many of the area’s most famous landmarks, like the iconic Hemingway House. The Conch Tour Train is a great way to explore the neighborhood with kids, but even if you don’t end up taking the train, the famous Southernmost Point is a must-see (and a great family photo opportunity).

Explore Old Town Key West condo rentals, house rentals, studios, and more


Condo rentals

View 41 Condo rentals

House rentals

View 29 House rentals


View 17 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Casa Bonita @ Duval Square R1
2 Bed | 2.5 Bath | Sleeps 6

Casa Bonita @ Duval Square R1 - Key West, FL

$694 avg / night
Casa Caribe at Duval Square, Unit R9
2 Bed | 2.5 Bath | Sleeps 6

Casa Caribe at Duval Square, Unit R9 - Key West, FL

$682 avg / night
Audubon House #6
1 Bed | 2 Bath | Sleeps 4

Audubon House #6 - Key West, FL

$457 avg / night
Duval Square Penthouse R19
2 Bed | 2.5 Bath | Sleeps 6

Duval Square Penthouse R19 - Key West, FL

$679 avg / night
Truman Suite #3
1 Bed | 1 Bath | Sleeps 2

Truman Suite #3 - Key West, FL

$296 avg / night

View 102 more homes

Recent Old Town Key West vacation rental reviews

The location was perfect in the quieter end of Key West. Loved the front porch to listen to live music and watch people walk by. The kitchen was well equipped for what we needed. Place was very clean and bed was very comfortable.
Nancy F. | Feb 2023
Cottage was great. Located about half way between north and south…we walked everywhere we wanted to go. Would stay there again
Michael B. | Feb 2023
very comfortible
Sandra W. | Feb 2023
Old Town Key West Frequently Asked Questions

Yes, 47 of our Old Town Key West homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 107 of our Old Town Key West vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Old Town Key West vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Old Town Key West team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Old Town Key West, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Snorkeling in the crystal Caribbean waters is an ever-popular activity in Old Town, and Fort Zachary Taylor Park is a great launching point for your snorkeling adventures. Make the most of Key West’s sunsets during your vacation rental stay: head out to Mallory Square or Sunset Pier for community festivities (which often include street performers, conch fritters, and tiki drinks). Duval Street, the main drag in Old Town, is a fun spot to spend an afternoon shopping or an evening bar-hopping. If you’re daydreaming about a classic Old Town Key West beach bungalow, browse our selection book your next getaway with Vacasa.