Must-See Historic Sites and Landmarks in Key West

key west shoreline, blue water

With its miles of shores and breathtaking sunsets, when you think of Key West, you think of sandy beaches and a relaxing getaway. This city has more to offer than a beautiful landscape, though! Located at the southernmost point of the continental United States, Key West draws travelers in with its laid-back charm, vibrant culture, and historical landmarks.

Whether you're a history buff or simply want to learn more about a new city, Key West has a lot to offer. From its captivating landmarks to fascinating museums, there's a lot more to Key West than meets the eye. Come with us as we explore the must-see historic sites and landmarks in Key West!

ernest hemingway museum

Ernest Hemingway House & Museum

This historical site is a must-see for literature lovers, but it has something to offer for everyone. Famed American author Ernest Hemingway's Key West home has been renovated into a museum where visitors can have a closer look into where he created some of his best works. Hemingway wrote one of his most renowned novels, “The Old Man & The Sea,” in Key West!

Hemingway and his wife Pauline landed in Key West by divine accident, a delayed streetcar causing them to be stuck in the area unexpectedly for a few weeks in the late 1920's. After just three weeks however, the pair fell in love with Key West, soon making it their permanent residence in 1931.

You’ll note many marvels as you make your way around the Hemingway residence. Ernest’s presence can still be felt in his studio, where he produced several of his most well-known works. There are even living remnants of Hemingway’s memory. Several cats wander the property who are likely descendants of his unusual six-toed tomcat Snowball. See if you can spot one!

You can also see the first in-ground pool in Key West here. It was built at an exorbitant cost, so much so that Hemingway joked, “Here, take the last penny I’ve got!” and placed a penny in the wet cement of the patio. It's still there today—put yourself to the test and see if you can find it!buouy, southermost point of us marker

Southernmost Point

A list of must-see historic sites and landmarks in Key West is incomplete without this famous tourist attraction. This permanently anchored concrete buoy represents the southernmost point in the continental United States, at 24.5465 °N, 81.7975 °W. The city originally marked this point with a cardboard sign, but it was stolen several times.

After years of replacing the old sign, Mayor Dennis Wardlow decided to make things permanent and placed the buoy as a tourist attraction on September 10th, 1983. Given that it’s made of concrete, it’s much harder to steal and has remained in place to this day. If you’re in the area, taking your picture with such an iconic landmark is worth the trip. No trip to Key West is complete without this famous photo op!

harry truman white house, little white house

Harry Truman’s Little White House

See how our 33rd US President spent much of his presidency (175 days to be exact) in the impeccably restored home of Harry Truman, aptly named the “Little White House”. Get ready to step into a time capsule; this historical relic looks just as it did in the forties and fifties, even keeping its original Christmas decorations up around the holidays.

Key West has served as a presidential retreat since 1880, when Ulysses S. Grant visited the island. Harry Truman followed this trend, turning to Key West as a peaceful oasis from the hustle and bustle of Washington D.C. You can take a museum tour and see where Truman lived, worked, played, and even held important government meetings during his presidency.

The Little White House is hosting a variety of events this summer, including the TRU-ly Amazing Art series and Truman’ s Tropical Fruit Festival. Attend a paint and sip night on Saturday, August 10th, or learn more about all of your favorite tropical fruits on Saturday, June 15th. The Fruit Festival will feature fresh fruit, a tropical tree sale, local vendors, and more!

overseas highway, highway florida keys

Overseas Highway

Imagine yourself cruising down Florida’s most scenic highway—an astonishing 42 bridges that leapfrog from key to key on the Overseas Highway, a true architectural wonder. The southernmost leg of US Highway 1 is called the “Highway that Goes to Sea,” allowing travelers to see ocean views for miles as they make their way to their destination (or just go for a joyride).

The trail of the Overseas Highway was initially forged in 1912 when Henry Flagler built an overseas train route from Miami to Key West. Much of this railroad was destroyed in a 1935 hurricane, ceasing its operations due to the damage incurred coupled with the economic downfall of the Great Depression.

The Overseas Highway was built along much of the original train route, debuting just three years later. In 1982, 37 original bridges were replaced with more comprehensive, sturdier spans. Nowadays, the highway passes fishing fleets, yachts, oceanfront villas, and enticing seafood restaurants. There’s so much to explore across all of Florida’s keys, and the Overseas Highway can take you there!

Book Your Trip Today with Dwell Key West!

With so many must-see historic sites and landmarks in Key West, it’s the perfect destination for a couple’s getaway or family trip. Our boutique properties offer unmatched luxury with top-of-the-line amenities designed to make your stay one of a kind. Whether you’re looking for a property with a pool or a full kitchen you can cook a meal in, Dwell Key West is here to meet your every need. Browse our collection of boutique accommodations and book your Key West stay directly with Dwell. We’ll see you soon!