Old Town Key West Vacation Rentals

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Make Old Town Key West your next getaway—choose from 106 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 42 Condo rentals

House rentals

View 30 House rentals


View 16 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Casa Caribe @ Duval Square R9
2 Bed | 2.5 Bath | Sleeps 6

Casa Caribe @ Duval Square R9 - Key West, FL

$734 avg / night
Monroe Suite
0 Bed | 1 Bath | Sleeps 2

Monroe Suite - Key West, FL

$318 avg / night
The Frontier Flat
1 Bed | 1 Bath | Sleeps 4

The Frontier Flat - Key West, FL

$540 avg / night
Audubon House
1 Bed | 2 Bath | Sleeps 4

Audubon House - Key West, FL

$508 avg / night
Truman @ Duval  - Unit B
1 Bed | 2 Bath | Sleeps 4

Truman @ Duval - Unit B - Key West, FL

$488 avg / night

View 101 more homes

Recent Old Town Key West vacation rental reviews

Clean, spacious, updated and beautiful property/location. I will be returning!
Jd F. | Aug 2022
We were very happy with our stay. The proximity to Duval Street and to the shipyard annex swimming pool was a great attribute to this location. The unit was very clean , and roomy enough for four adults to share. We are looking forward to our next trip to Key West and looking forward to staying at this property again!
Marsha P. | Aug 2022
Location , foliage, proximity , lots of towels, great customer service
Suzanne L. | Aug 2022
Old Town Key West Frequently Asked Questions

Yes, 49 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. 106 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.