Old Town Key West Vacation Rentals

Compare 102 vacation rentals.
USA > Florida > Old Town Key West

Make Old Town Key West your next getaway

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

housing_type_condo.jpg

Condo rentals

View 36 Condo rentals
housing_type_house.jpg

House rentals

View 28 House rentals
housing_type_studio.jpg

Studios

View 11 Studios

Old Town Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$167 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$335 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$328 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$205 avg / night
Heron Suite
1 Bedroom | 1 Bath | Sleeps 4

Heron Suite - Key West, FL

$340 avg / night

View 97 more homes

Recent Old Town Key West vacation rental reviews

The small and quiet location was perfect for a group who also wanted to enjoy the nightlife down towards the other side of Duval. The outdoor space was amazing with the shaded pool, and cool breeze. Will stay again!
Lauren Z. | Apr 2024
The place is fabulous! Location was the best for parking a car was private and quiet. The place was just perfect for 14 of us. I highly recommend for large groups. We would definitely come back here again. Maria
maria m. | Apr 2024
Great location.
Edward S. | Apr 2024
Old Town Key West vacation rental FAQ

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. 102 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 and book your next getaway with Vacasa.