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
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$1,102 avg / night
4.5 (121)
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$901 avg / night
4.37 (104)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$354 avg / night
4.38 (47)
Truman @ Duval - Unit E
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit E - Key West, FL

$317 avg / night
4.21 (38)
Orchid Suite
1 Bedroom | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$415 avg / night
4.54 (71)

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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

Great location. Plenty of room and clean.
Steve N. | Dec 2024
A wonderful condo with a fantastic location!!! We walked everywhere!! Good security!! We loved it!!
Eileen F. | Dec 2024
We really enjoyed our stay, my husband who is ex military, so loved being on a military base with reveille, national anthem, retreat and taps being played. The sunset view was fantastic. The location was very convenient to everything we wanted to visit. The kitchen had all we needed, the beds were excellent, and there were plenty of towels.The condo was very bright and clean. We had trouble finding the lockbox for the keys and fob. (It's not at the assigned parking place). The keys didn't work the gates to Truman Annex but this was corrected by VACASA. Some suggestions to improve the experience would be to deep clean the tile floors and it would be great if some lamps and end tables could be placed in the living room for reading. A few rugs would improve the acoustic quality of the space. We loved the experience and will be back!
Benjamin S. | 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).

Browse dog-friendly homes >

Yes. 75 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.

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