Key West is the last of the Florida Keys, which stretch for miles into the Atlantic Ocean and the Gulf of Mexico and the southernmost point in the continental United States. This popular vacation destination sees visitors throughout the year due to its mild winters. A Key West vacation rental places you in the center of outdoor fun, fine dining, an active nightlife scene, and some unique shopping opportunities. Go deep-sea fishing with a charter company, eat Key Lime pie, and see where Ernest Hemingway wrote some of his famous novels.

1. Visit the Southernmost Point Buoy

Sitting less than 20 feet above sea level, the Southernmost Point Buoy marks the southernmost point in the lower 48 states of the United States. This anchored concrete buoy is painted in bright colors, so you can take plenty of photos. From this point, it’s just 90 miles to the coast of Cuba.

2. Go Bike Riding With Lloyd’s Tropical Bike Tour

On your first day on Key West, see all the sights and get the lay of the land by spending a couple of hours on Lloyd’s Tropical Bike Tour. This bike tour lasts around two hours and takes you by all the major sites and activities. During your ride, Lloyd shares local history and colorful stories about life in the Keys. Although it’s a long ride, most of the roads are flat, so it’s a very easy ride.

3. Go Diving at the Vandenberg

A former Navy ship, the Vandenberg, was intentionally sunk in the Florida Keys National Marine Sanctuary to create a new coral reef. The remains of this ship and new growth reef lie about 150 feet below the water. Bring your own scuba gear and store it at your vacation rental until it’s time to go diving. See all the beautiful fish and undersea life that make their home close to the reef.

Find the perfect Key West vacation rental on is the world's #1 vacation rental search engine with over 10 million properties!

4. See a Civil War Reenactment at the Fort Zachary Taylor Historic State Park

Take a tour of the Fort Zachary Taylor Historic State Park to learn more about the Florida Keys’ role in the American Civil War. See the remaining buildings and fort walls while a ranger explains the history. Frequent Civil War reenactments take place here, and some of them continue for days. Pack a picnic lunch or grab something from one of the restaurants near the southern end of Key West to enjoy an alfresco meal.

5. Visit the Ernest Hemingway House and Museum

Built in 1851, the Ernest Hemingway House is a Spanish Colonial style mansion made from local rocks. Tour the home and visit the museum to learn more about the house and life in the Keys during Hemingway’s era. While you’re walking around the property, keep your eyes peeled for the six-toed cats that live here; these are descendants of Hemingway’s cat.

6. Look for Dolphins With Fun in the Sun Private Charters

Head out on the water for an afternoon of looking for dolphins and snorkeling in the clear waters with Fun in the Sun Private Charters. With three boats that hold up to six passengers, this charter company is always ready to take you off for an adventure. Charters last between two and a half and six hours, so you can explore hidden coves, drop a fishing line, and look for dolphins jumping out of the water.

7. Relax at the Key West Butterfly and Nature Conservatory

The Key West Butterfly and Nature Conservatory has more than 60 species of butterflies and 20 species of birds. Learn more about these beautiful creatures during a tour of the conservatory. Located in the middle of downtown Key West, this nature conservatory is your oasis for some peace and quiet as you watch the butterflies flit by you. Before leaving, stop by the gift shop, which features the work of local artist Sam Trophia.

8. Climb Abroad the U.S. Coast Guard Cutter Ingham Maritime Museum

In service from 1936 to 1986, the CGC Ingham was a workhorse of the Coast Guard and saw a lot of maritime history. You can learn more about maritime history and the U.S. Coast Guard when you climb onto the U.S. Coast Guard Cutter Ingham Maritime Museum. Take a guided tour to learn more about daily life on one of these ships as you walk along the decks and see the crew quarters and the mess hall.

9. Cool off at Lagerhead’s Beach Bar

Just steps from pristine white sand, Lagerhead’s Beach Bar is a favorite among locals and tourists. It sits in a plain white building that looks like it’s been there forever. Grab a cold beer and one of Lagerhead’s famous fish tacos, and watch the surf roll in. You can also rent fishing gear and snorkeling gear from this bar, so you have something to do after lunch.

10. See the Keys From the Air With Key West Seaplane Adventures

Take to the air and enjoy stunning scenery with Key West Seaplane Adventures. The tour takes you to the Dry Tortugas National Park (only accessible by plane or boat) and lands, so you can do a little exploring. When you board, you receive a headset to hear the pilot provide you with more information about the Keys and point out various sights, such as shipwrecks.

Ready to go? Check out these amazing Key West vacation rentals on