Old Town Key West Vacation Rentals

Compare 68 vacation rentals.
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USA > Florida > Old Town Key West

Make Old Town Key West your next getaway

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 house rentals, condo rentals, apartments, and more

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House rentals

View 24 House rentals
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Condo rentals

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Apartments

View 6 Apartments

Popular amenities for Old Town Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Key Lime Calypso
2 Bedroom | 1 Bath | Sleeps 6

Key Lime Calypso - Key West, FL

$899 avg / night
4.54 (110)
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$861 avg / night
4.33 (112)
Old Town Garden Villas - Andros Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$351 avg / night
4.75 (135)
Truman Suite #3
0 Bedroom | 1 Bath | Sleeps 2

Truman Suite #3 - Key West, FL

$287 avg / night
4.32 (160)
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 7

Hemingway's View - Key West, FL

$1,023 avg / night
4.42 (130)

View 63 more homes

Browse more vacation rental amenities in Old Town Key West

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony | Bikes

Recent Old Town Key West guest reviews

Great location and spacious accommodation
Terry M. | May 2025
The comfort and overall quality of the place. It was close to everywhere we wanted to be. I would stay there again.
Brenda M. | May 2025
Unit was on the 2nd floor of a multi-unit house just a block away from Duval Street and very close to the free on/off bus to take you everywhere you want to go. Staying here made Key West very walkable. Parking was very convenient on site. Location is surrounded by palm trees and lush foliage that gives the 'old Florida' feel. Would definitely stay here again.
Kathy W. | May 2025
Old Town Key West vacation rental FAQ

Yes, 21 of our Old Town Key West homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 68 of our Old Town Key West vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Old Town Key West vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Old Town Key West team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Old Town Key West, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
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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 and book your next getaway with Vacasa.

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Lower Keys, FL   |   Mallory Square - Key West   |   Bahama Village - Key West   |   Historic Key West   |   Papa's Hideaway - Key West, FL   |   Shipyard Condos - Key West   |   Duval Square - Key West   |   Key West   |   Florida
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