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

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Condo rentals

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House rentals

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Studios

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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

$165 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$328 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$336 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$212 avg / night
Heron Suite
1 Bedroom | 1 Bath | Sleeps 4

Heron Suite - Key West, FL

$340 avg / night

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Browse more vacation rental amenities in Old Town Key West

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony | Bikes

Recent Old Town Key West vacation rental reviews

Great location right near the south end of duval st. They have 2 washers and dryers on property which both worked great for my husband an I. We were able to obtain free street parking adjacent to the home. quiet and cozy little spot.
Erica O. | Apr 2024
Location, cleanliness, atmosphere, amenities combined with an oasis made for a great stay. No surprises.
Michael M. | Apr 2024
We loved this beautiful home. The house was very comfortable and in the perfect location to walk to attractions such as Mallory Square, Duval St., The Hemingway House and the Annex waterfront park and Blue Heaven. Also, it is just steps to the property pool. Very convenient. There were only 4 chairs at the table so if 6 people stayed at this property you couldn't all eat together but those that were there were very comfortable. There were plenty of silverware, plates, cups, glasses, bowls as well as cooking and serving stuff although we mostly ate out. The parking space was a little bit of a walk but that is what were there for to enjoy being outside and enjoying this amazing and somewhat quirky Key. We loved every moment and would totally stay in this property again.
Rick a. | 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.

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