Explore Old Town on Your Next Vacation to Key West

From art galleries to well-known writers’ spots, when you visit Key West Old Town, you just know you are in the midst of history—the reason, actually, that it’s called Historic Key West. Not far from many places to stay in Key West (most up to 5-bedroom vacation homes), this charming and storied area is a Florida Keys “must-visit” when you come to visit! Particularly if you’re looking for a fun day that’s a break from the waves and the sand, then Old Town Key West is where you’ll want to spend that time. So where exactly is it and what are some things to do in Key West Old Town? Let’s find out!

Where is Old Town?

Designated as a U.S. Historic District in 1971, Old Town is the name bestowed upon the Historic Key West District, which is found on the western side of Key West (the last of the string of islands that make up the Florida Keys). Most of the businesses and tourist attractions are found in this part of the island of Key West, Florida. These Key West attractions include an aquarium, museums, and historic homes and buildings.

mallory square sign
Photo from Unsplash

As you would expect, many of these locations are among the top “things to do” when you visit Key West Old Town, with some found on Key West Duval Street—basically the town’s Main Street highlighted by Victorian architecture, boutiques, and art galleries. Duval Street also has a teeming nightlife, when tourists turn the street alive as they eat and drink at the several well-known bars and restaurants lining the avenue.

Let’s take a peek at some of those things to do so you can see how much adventure and enjoyment awaits you in Old Town Key West.

Plan Your Key West Vacation

When looking for a place to stay near Old Town, check out our selection of luxury Key West rentals. You can be close to all that you want to do and see while experiencing this little bit of history.

Things to Do

So, what might a day in Key West Old Town look like?

It might start by taking a sightseeing trolley or the Conch Train Tour that will take you through a narrated guide along the streets of the area as you learn about the key figures and sites that shaped its history. You might spend some time at places like the Hemingway House, where the famous author spent most of the 1930s, or at a museum presenting an exhibit of memorabilia owned by playwright Tennessee Williams.

southernmost point of continental US

You’d be remiss not the stop at the Key West Lighthouse and accompanying keeper’s quarters museum. And NOT to miss is the opportunity to stand at the Southernmost Point of the Continental US and take a photo at the aptly named Southernmost Point Buoy several blocks from the lighthouse. It’s THE photo opportunity of your visit!

Dine for lunch and dinner at any one of the great restaurants in the area in between shopping at nearby Mallory Square. Later, you might hit Duval Street as the bars and restaurants welcome those enjoying the night sights.

And that’s just one way to spend your day in Old Town; there are so many other Key West attractions in and around the area that a week of vacation here might simply not be enough time.

Photo from Unsplash

Where to Stay

outside view of property at sunset

Want top luxury in a 3-, 4-, or 5-bedroom vacation home near but not necessarily directly in Old Town? Our Key West rentals with a dock, offer waterfront views and slips for our boaters. Our vacation homes offer heated pools and fully equipped kitchens. Truly, your choice of a home away from home will underscore your Key West vacation.

When it comes to Key West vacation rentals, the worst thing that can be said is that you might forgo some attractions and other notable sites just to spend a day enjoying the beautiful vacation home and all the amenities. SO whether you are staying in Paradise Harbor, Key Haven Estates, or one of our Key West condo rentals at Bayfront Suites, you cannot go wrong!