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 129 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 31 House rentals


View 29 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Last Minute 3D Tour
3 Bed | 2 Bath | Sleeps 6

Last Minute - Key West, FL

From $514
Helen's Hideaway 3D Tour
2 Bed | 2 Bath | Sleeps 6

Helen's Hideaway - Key West, FL

From $512
Truman @ Duval - Two Bedroom 3D Tour
2 Bed | 1 Bath | Sleeps 4

Truman @ Duval - Two Bedroom - Key West, FL

From $228
Monroe Suite 3D Tour
0 Bed | 1 Bath | Sleeps 2

Monroe Suite - Key West, FL

From $134
Audubon House 3D Tour
1 Bed | 2 Bath | Sleeps 4

Audubon House - Key West, FL

From $199

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Recent Old Town Key West vacation rental reviews

We had a family vacation with our 4 adult children, significant others & grandchildren. The Tropical village was amazing & everyone had their own house. Make sure to bring coffee filters (cone). The coffee they leave for you is definitely very weak so order coffee also. There are 2 washers & dryers on site outside in out building, dryers take almost all day to dry 1 load of laundry. Don’t bring any beach towels with you, there are plenty of Vacasa beach towels in every house. We will be planning our stay here for next year very soon!
Stephanie J. | Jul 2021
This was a home away from home. Very clean and within walking distance to everything we needed! Can’t wait to come back!
Jodee B. | Jul 2021
Very comfortable
Nancy B. | Jul 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.