Old Town Key West Vacation Rentals

Compare 82 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

housing_type_house.jpg

House rentals

View 30 House rentals
housing_type_condo.jpg

Condo rentals

View 24 Condo rentals
housing_type_studio.jpg

Studios

View 9 Studios

Explore more vacation rental amenities in Old Town Key West

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

Old Town Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bed | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$290 avg / night
4.52 (64)
Hemingway's View
3 Bed | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$1,316 avg / night
4.5 (120)
Amelia House
3 Bed | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$1,098 avg / night
4.37 (102)
Truman @ Duval - Studio A
0 Bed | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$431 avg / night
4.36 (44)
Orchid Suite
1 Bed | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$433 avg / night
4.54 (71)

View 77 more homes

Recent Old Town Key West vacation rental reviews

We loved the location, close to and walkable to so many good restaurants and sights. The accommodations were very clean and comfortable, nicely appointed. We highly recommend the Julia Whitehead Guest Suites.
Linda P. | Nov 2024
The house itself was incredible. Very clean well laid out. This is in direct line from the airport so a lot of planes overhead during the day. Unfortunately they were installing a roof on the house next-door and we could not use the pool because of all the sawdust. I would definitely stay there again. I just make sure there were not any Construction.
Jeffery K. | Nov 2024
Great location, comfortable bed and big refrigerator. Easy entry with code access. Would definitely stay again!
Lisa B. | Nov 2024
Old Town Key West Frequently Asked Questions

Yes, 29 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. 82 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.

People also search for

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
Show more