Old Town Key West Vacation Rentals

Compare 58 vacation rentals.
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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 19 House rentals
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Condo rentals

View 17 Condo rentals
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Apartments

View 5 Apartments

Explore more vacation rental amenities in Old Town Key West

Pool | Ocean view | Water view | Waterfront | A/C | Washer/dryer | Balcony | Bikes | Pack-N-Play | Beach access

Old Town Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Old Town Garden Villas - Andros Suite
1 Bed | 1.5 Bath | Sleeps 4

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

$418 avg / night
(excludes fees and taxes)
4.73 (150)
Old Town Garden Villas - Abaco Suite
1 Bed | 1.5 Bath | Sleeps 4

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

$543 avg / night
(excludes fees and taxes)
4.66 (131)
Conch Casa
2 Bed | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

$658 avg / night
(excludes fees and taxes)
4.47 (132)
Hemingway's View
3 Bed | 2 Bath | Sleeps 6

Hemingway's View - Key West, FL

$811 avg / night
(excludes fees and taxes)
4.41 (147)
Seagrass Suite
1 Bed | 1 Bath | Sleeps 2

Seagrass Suite - Key West, FL

$328 avg / night
(excludes fees and taxes)
4.74 (38)

View 53 more homes

Recent Old Town Key West vacation rental reviews

Everything
robert s. | Mar 2026
When originally booking this home, I read a lot of reviews good and bad on other platforms. Cleanliness and upkeep to an older cottage were the main recurring issues. I reached out to property management and they were careful enough in reassuring me of my concerns they responded by Email and phone months in advance of our reservation and were reachable just before and during our stay. None of the deficiencies I had come across in reviews over past years seem to still exist. Which tells me the owner and management pay attention and fix problems. Was a very clean and lovely stay. They best location. Very clean. Mind you, it isn't new. It's an older cottage. Vacasa office is across the street. They were very helpful with recommendations and holding our bags before check in and after check out. I think in general a 4 pm checkin could be 3pm and a 10 am check out could be an 11am. The cleaners were a little too eager. They were there at 9:55am already trying to get in when when we were still moving our suitcases to the front door.
Evan F. | Mar 2026
We absolutely loved our stay here in Key West! It was perfect for us and so incredibly cute—exactly the vibe we were hoping for. The bathroom was spacious and beautifully done, which made getting ready feel a little extra luxurious. The bed was amazing—super comfortable and honestly one of the best parts after long days of exploring. The kitchen was just what we needed. We didn’t do a ton of cooking, but having a fridge was a game changer for drinks, snacks, and leftovers. Everything felt clean, well-kept, and thoughtfully put together. The location was also great—close enough to everything we wanted to do, but still felt like a relaxing little escape. Overall, it was the perfect spot for our trip and we would definitely stay here again!
Morgan B. | Mar 2026
Old Town Key West Frequently Asked Questions

Yes, 19 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. 58 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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Old Town Key West, log in to Trip Manager to see options available for your specific trip.

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 and book your next getaway with Vacasa.

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