Old Town Key West Vacation Rentals

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Make Old Town Key West your next getaway—choose from 102 great vacation rentals

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 45 Condo rentals

House rentals

View 24 House rentals


View 15 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Yellowfin Ledge On Duval 3D Tour
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

From $123
Heron Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Heron Suite - Key West, FL

From $111
Truman @ Duval - One Bedroom 3D Tour
1 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - One Bedroom - Key West, FL

From $195
Old Town Garden Villas - Abaco Suite 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 4

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

From $225
Old Town Garden Villas - Bermuda Suite 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 4

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

From $210

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Recent Old Town Key West vacation rental reviews

The condo was very clean , it had everything you could possibly need for a great stay!
Edward O. | Dec 2021
The house was well maintained and appeared to be recently remodeled. Kitchen had everything we needed, beds were comfy. The pool/deck area was beautiful and we spent much of our stay in and around the pool. Easy walk to restaurants, bars and grocery store. I will definitely try to stay here again!
Susan S. | Dec 2021
This house was clean and well kept. Grounds were well kept and the pool was nice. The only complaint would be the fact that there was a bag of dirty bedding that sat on the front porch for 2-3 days and garbage and recyclables on the back porch the whole time we were there from the guests before us! We called about it twice but nothing was ever done about it. We also called about an issue with our Roku remote(which we eventually figured out), and were told a maintenance person was on the way. We never knew if he showed or not. No note, no call….a shame because it was such a nice place.
Patti H. | Dec 2021

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.