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

housing_type_house.jpg

House rentals

View 27 House rentals
housing_type_condo.jpg

Condo rentals

View 21 Condo rentals
housing_type_studio.jpg

Studios

View 8 Studios

Popular amenities for Old Town Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Windward Isle
2 Bedroom | 1 Bath | Sleeps 6

Windward Isle - Key West, FL

$622 avg / night
4.32 (41)
Truman @ Duval - Unit F
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit F - Key West, FL

$343 avg / night
4.23 (31)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$365 avg / night
4.4 (48)
Leeward Isle
2 Bedroom | 1 Bath | Sleeps 6

Leeward Isle - Key West, FL

$550 avg / night
4.52 (60)
Orchid Suite
1 Bedroom | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$305 avg / night
4.55 (73)

View 70 more homes

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

Just finished a quick stay, and enjoyed everything. Love the access to Duval Street. They’ve done a great job with the house and we plan to stay again but longer this time.
Kevin C. | Jan 2025
What a wonderful spot for a couple to spend their downtime to recharge while out and about in Key West. It was a perfect spot to take a nap, whip up a meal, or just relax in the A/C while reading a book. This property sits back with a private, gated entry which makes it feel more secluded and private. Wonderful spot for two to enjoy their time together.
James F. | Jan 2025
The home was beautiful and accurate in description and photos. Quiet residential area with its location basically in the center of Old Town which makes it very walkable to any point in the area. Will definitely look into staying here again the next time we want to spend a few days in Key West.
Gary M. | Jan 2025
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
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
Show more