Old Town Key West Vacation Rentals

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Make Old Town Key West your next getaway—choose from 139 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

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House rentals

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View 30 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Conch Casa 3D Tour
2 Bed | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

From $276
Old Town Garden Villas - Andros Suite 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

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

From $169
Key Lime Calypso 3D Tour
2 Bed | 1 Bath | Sleeps 6

Key Lime Calypso - Key West, FL

From $300
Kate's Krawl Off Duval 3D Tour
1 Bed | 1 Bath | Sleeps 4

Kate's Krawl Off Duval - Key West, FL

From $227
The Galleria - Claude Monet Suite #3 3D Tour
0 Bed | 1 Bath | Sleeps 4

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

From $122

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Recent Old Town Key West vacation rental reviews

quiet and cozy cottage ... nice location with parking on the street directly out front . The locked gate leading to the front courtyard gave us a very secure area to relax at the end of a busy day !
Laura L. | Jun 2021
We had such a good time. Close to downtown. Very comfortable. Nice pool.
linda G. | Jun 2021
The location was perfect. Pretty much everything as expected and as advertised. Host was very responsive to questions. Easy check in check out process. Loved keyless entry. Felt very safe in this location.
Betty M. | 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.