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 135 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

View 34 House rentals


View 26 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Oceana Suite 3D Tour
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Oceana Suite - Key West, FL

From $275
Honey Bun Hideaway 3D Tour
0 Bed | 1 Bath | Sleeps 2

Honey Bun Hideaway - Key West, FL

From $124
The Galleria - Claude Monet Suite #3 3D Tour
0 Bed | 1 Bath | Sleeps 4

The Galleria - Claude Monet Suite #3 - Key West, FL

From $116
Old Town Garden Villas - Bermuda Suite 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

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

From $159
Duval Square Penthouse R19 3D Tour
2 Bed | 2.5 Bath | Sleeps 6

Duval Square Penthouse R19 - Key West, FL

From $296

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Recent Old Town Key West vacation rental reviews

Great location and we enjoyed it. However, If you’re a light sleeper this may be not be for you. It has a lot of traffic noise. Also if the front patio has a tarp over it for afternoon sun it would be a great place to relax there.
Jenny T. | Jun 2021
Small beach hut in the middle of the action in Old Town Key West. Noisy during the weekends and parking was difficult due to neighboring B&B.
Shannon S. | Jun 2021
Great location close enough to walk to Duvall street , harbor park and beach within bike riding and short car distance . Wonderful accommodations looks just like the pictures , and very prompt service if there are issues ! I will definitely stay again Thank you !
KARIN L. | Jun 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.