Old Town Key West Vacation Rentals

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USA > Florida > Old Town Key West

Make Old Town Key West your next getaway—choose from 130 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 47 Condo rentals

House rentals

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View 27 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Old Town Garden Villas - Caribbean Suite 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

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

From $193
Conch Casa 3D Tour
2 Bed | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

From $174
Last Minute 3D Tour
3 Bed | 2 Bath | Sleeps 6

Last Minute - Key West, FL

From $323
Yellowfin Ledge On Duval 3D Tour
1 Bed | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

From $130
Osprey Suite 3D Tour
0 Bed | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

From $87

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Recent Old Town Key West vacation rental reviews

Great location. Private and quiet, yet easy to get around. Clean, has what's needed. Would recommend.
Wendy D. | Sep 2021
Very clean unit with access to pool, elevator and garage within steps. Close proximity to many shops, restaurants, and attractions.
MARY S. | Sep 2021
This house has everything you need. From a full kitchen, living room, etc. You could truly live in this home. The courtyard is a nice quiet place and maintained very well. You are just one block off Duvall Street where all the action is. We walked everywhere and never used the rental car we had once we got there. There is only street parking, but we did not have an issue with finding a spot. We will definitely be staying here again. I can’t say enough good things about this house.
Justin P. | Sep 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.