Old Town Key West Vacation Rentals

Compare 75 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 house rentals, condo rentals, studios, and more

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House rentals

View 27 House rentals
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Condo rentals

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Studios

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Popular amenities for Old Town Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$919 avg / night
4.33 (105)
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$1,151 avg / night
4.5 (121)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$363 avg / night
4.38 (47)
Orchid Suite
1 Bedroom | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$320 avg / night
4.54 (72)
Truman @ Duval - Unit E
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit E - Key West, FL

$324 avg / night
4.21 (39)

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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 guest reviews

We loved where this house was located adjacent to Devall Street. It was convenient and we were able to walk everywhere. We were even able to hear music coming from the local bars which we enjoyed. Everything was really clean and the pool was heated, which was great in mid December.
Hawley K. | Dec 2024
Because my son and only child died, i was unable to make the stay. But my friend who did stay told be it wqas great and they are going to rent the house again soon. Thanks for all your help
anthony k. | Dec 2024
Duval Street was not even 60s away and Hemingway House was literally around the corner
Dave M. | Dec 2024
Old Town Key West vacation rental FAQ

Yes, 22 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).

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Yes. 75 of our Old Town Key West vacation rentals have internet access, so you can stay connected throughout your trip.

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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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Lower Keys, FL   |   Mallory Square - Key West   |   Bahama Village - Key West   |   Historic Key West   |   Papa's Hideaway - Key West, FL   |   Shipyard Condos - Key West   |   Duval Square - Key West   |   Key West   |   Florida
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