Old Town Key West Vacation Rentals

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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

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House rentals

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Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Truman Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Truman Suite - Key West, FL

From $122
Tropical Retreat 3D Tour
3 Bedroom | 3.5 Bath | Sleeps 8

Tropical Retreat - Key West, FL

From $523
Banana Split 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Banana Split - Key West, FL

From $170
Sugar Pie Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Sugar Pie Suite - Key West, FL

From $82
Yellowfin Ledge On Duval 3D Tour
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

From $105

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Recent Old Town Key West vacation rental reviews

We were a group of 12 adults, and this house was exactly what we wanted. Location was close to almost every thing we wanted to visit. Plenty of space a and private rooms and bathrooms. We will rent this house again.
Craig F. | Sep 2021
Do not hesitate - they are honest and the property is exactly what you see.
Steven L. | Sep 2021
We loved staying at Papa’s Hideaway! Beautiful, so convenient to all activities of the city and within walking distance. Only slight issue was being so dark at night since night pool and patio lights did not turn on till 10:30 pm, and they never fixed it even after asking multiple times. Also one Suggestion is to send out LOCAL phone number for Vacasa to person renting. Could be in the welcome email with codes. All we had were 800#’s. Either way we would recommend to stay there again for a large group like our of 12. ☀️🌴🐓🦎
Laura B. | 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.