Key West packs centuries of history, culture, and coastal beauty into a small island, and its most famous sights sit within easy reach of one another. Exploring Key West’s top landmarks is one of the best ways to understand what makes this southernmost city so special. The team at Compass Realty has put together a guide to the icons worth your time, along with a few tips to make a sightseeing trip more efficient and fun.
Historic Key West Landmarks at the Southern End
Several signature stops cluster near Whitehead and South streets. The Southernmost Point Buoy marks the spot famously noted as 90 miles from Cuba, and it ranks among the country’s most photographed places. Arrive early to beat the crowds and the midday heat.
A short walk away sits the Ernest Hemingway Home and Museum, the Spanish Colonial house where the author lived and wrote during the 1930s. Descendants of his famous six-toed cats still roam the historic grounds. Right across the street, the Key West Lighthouse rewards the climb up its 88 steps with sweeping island views. The Key West Butterfly and Nature Conservatory rounds out the area with a glass-enclosed habitat full of butterflies from around the world.
Waterfront Landmarks Near Mallory Square
At the other end of Old Town, the harbor draws visitors for its history and its sunsets. Mallory Square hosts the nightly Sunset Celebration, a gathering of street performers, artists, and food carts that begins about two hours before sundown. The Key West Aquarium and the Key West Shipwreck Treasure Museum sit nearby, giving families plenty to explore.
Steps away in the Truman Annex neighborhood, the Harry S. Truman Little White House offers a guided tour of the retreat where the 33rd president spent 175 days in office. Built in 1890, it remains Florida’s only presidential site. Pair it with this historic state park, home to a Civil War-era fort and some of the island’s best snorkeling.
Connecting the Landmarks on Duval Street
Running between the two clusters is Duval Street, the mile-long main drag that stretches from the Gulf of Mexico to the Atlantic. Lined with shops, galleries, restaurants, and bars, it ties the island’s attractions together. Because Key West measures roughly 4 miles by 2 miles, reaching these Key West landmarks on foot or by bike is simple and scenic.
Stay Near Key West’s Landmarks
Seeing the best Key West landmarks is easier when your home base sits close to the action. At Compass Realty, we offer vacation rentals across the island, putting you near the area’s top attractions. Our Key West vacation rentals range from condos to private homes, and feature kitchens, comfortable living areas, and easy access to the sights. When you are ready to book, reserve online or call us at 305-292-1881.
