Old Town Key West Vacation Rentals

Compare 108 vacation rentals with savings up to 30% off this summer.
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


Condo rentals

View 38 Condo rentals

House rentals

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View 12 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Mermaid's Retreat
1 Bedroom | 1.5 Bath | Sleeps 2

Mermaid's Retreat - Key West, FL

$278 avg / night
Key Lime Calypso
2 Bedroom | 1 Bath | Sleeps 6

Key Lime Calypso - Key West, FL

$467 avg / night
Seagrass Suite
1 Bedroom | 1 Bath | Sleeps 2

Seagrass Suite - Key West, FL

$273 avg / night
Old Town Garden Villas - Andros Suite
1 Bedroom | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Andros Suite - Key West, FL

$275 avg / night
Truman @ Duval - Unit B
1 Bedroom | 2 Bath | Sleeps 4

Truman @ Duval - Unit B - Key West, FL

$290 avg / night

View 103 more homes

Recent Old Town Key West vacation rental reviews

The location was fantastic! It was even more convenient that each bedroom has its own bathroom and there was a half bath on the main level. The unit is immediately adjacent to the pool, which was also great. Pool closes at dusk/9pm, so there was no issue with late night partying in the pool area.
Todd P. | Jun 2023
We loved the location and the backyard space. The pool was larger than expected and was quite the oasis. There was music every night from a neighboring bar but it’s hard to hear inside. We could walk absolutely everywhere. Loved it!
Melissa T. | Jun 2023
Pics don't do it justice. Quiet and relaxing and centrally located make it a place to return to.
Thomas Y. | May 2023
Old Town Key West vacation rental FAQ

Yes, 50 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. 108 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.

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.