Learn About Key West History on Vacation

Key West is a city where every street tells a story and history comes alive. Unravel the rich history of Key West during your getaway and learn about the island’s rich maritime heritage, military past, famous residents, and diverse culture. Grab a drink at a bar that’s been open since the 1800s, stroll through the colorful architecture of Old Town, and visit the home where Ernest Hemingway once resided. Book one of our vacation rentals in the heart of Old Town and enjoy staying in the historic district, just minutes from the area’s rich history and attractions!

Visit the Homes of Literary Legends and US Presidents

When you visit Key West, you will be walking in the footsteps of legends. Visit the historic homes of Key West’s most famous residents and learn how they contributed to the island’s history:

Ernest Hemingway Home and Museum: See where Ernest Hemingway resided and wrote during the years he called Key West home.
Harry S. Truman Little White House: Visit this historic home, best known for being the winter residence of Harry Truman during his presidency.
Tennessee Williams Museum: Learn about Williams’ literary accomplishments and life in Key West at this local museum.

Discover Key West Maritime and Military History

Key West’s history has long been tied to the water. Our convenient location on the Gulf of Mexico and the Atlantic Ocean drew the Navy here in the 1820s to establish military forts. Later on, our waters, industries like wrecking, salvaging, and salt manufacturing thrived. Learn about all this and more at these historic sites:

Fort Zachary Taylor Historic State Park: Step back in time and explore this historic fort that played an important role in the Civil War and the Spanish-American War.
Fort East Martello Museum: Explore this unique Civil War fort, featuring exhibits on the Civil War, industries, folk art, and even ghostly encounters.
Key West Lighthouse Museum: Climb the stairs of the island’s historic lighthouse and learn about maritime history while soaking in the views.

Uncover the Rich Cultural Heritage

The people make the place. And that’s abundantly clear in Key West. The island’s diverse cultures and people are what make us who we are and what we are today. Learn the story of the indigenous people who first called the island home, immigrants who came to Key West and helped it thrive, and much more:

Key West Museum of Art & History: Learn about two centuries of history, art, and people on the island in a historic building originally used as the island’s post office.
Historic Key West Cemetery: Walk through the historic cemetery, featuring many unique tombstones and stories of past residents.
San Carlos Institute: Explore this unique historic site, founded in the 1870s by Cuban exiles. Today, it serves as a community space and preserves the rich history of Cubans on the island.

Book Your Vacation Rental in the Key West Historic District

These are just a few of the ways you can learn about Key West’s history during your visit. Discover even more Key West historical tours and sites, including Sloppy Joe Bar, Key West Historic Seaport, and Mallory Square. Stay close to it all with our Key West vacation rentals in the historic district, ranging from charming one-bedroom cottages to grand estates. Find the perfect rental for your Florida vacation and book with us today!

7 Key West Attractions to Add to Your Vacation Itinerary

For an island of only a few square miles, Key West has an impressive number of attractions and activities that keep visitors coming back year after year. If this is your first time visiting Key West, there are a few must-see attractions that will help you make the most of your island getaway. From the vibrant atmosphere of Duval Street to the beautiful beaches of Fort Zachary, there is something for everyone. Stay close to the island’s top attractions with Rent Key West Vacations and enjoy the perfect basecamp for your adventures!

1. Southernmost Point Buoy

Key West is famous for many things, including being the southernmost city in the continental United States. Make a stop at the Southernmost Point Buoy and snap your picture at this iconic landmark!

Important Note: The roads around the buoy are undergoing repairs. The temporary location is at 1499 Duval Street.

2. Ernest Hemingway Home and Museum

See the residence where Ernest Hemingway lived and worked during his time in Key West: Ernest Hemingway Home and Museum. Stroll through the gardens, meet the adorable six-toed cats, see photos from his fishing adventures, and shop for unique mementos.

3. Key West Lighthouse

Just across the street from the Hemingway Museum is the historic Key West Lighthouse, opened in 1848. Climb the stairs to the top and admire the panoramic views of the island. Then visit the museum to learn more about the history of the Florida Keys.

4. Fort Zachary Taylor Historic State Park

Fort Zachary Taylor has something for everyone, blending history and nature in one destination. Tour the historic fort, learn about its important role in the Civil War, and see artifacts like cannons and port guns. Beyond the fort, you can access a scenic beach perfect for swimming, snorkeling, paddling, and fishing.

5. Smathers Beach

Smathers Beach is the largest beach in Key West and a must-visit during your vacation. Plan a classic beach day and relax in the soft white sand, and soak up the sunshine. You can also access several water activities with Sunset Watersports from here, including parasailing, jet skiing, and sunset cruises.

6. Duval Street

Duval Street is the heart of downtown Key West and the hub for shopping, dining, and entertainment in town. Take the Old Town Trolley and hop on and off the trolley to grab a drink at famous bars like Sloppy Joe’s and Green Parrot. You are also close to the shops and attractions of Mallory Square!

7. Key West Butterfly and Nature Conservatory

Walk amongst hundreds of colorful butterflies at the Key West Butterfly and Nature Conservatory. Stroll through the tropical gardens, observe over 60 butterfly species, and learn about butterflies’ role in the natural world.

Reserve Key West Vacation Rentals Today

Book your trip with Rent Key West Vacations and add these Key West attractions to your itinerary. Find even more things to do in Key West during your stay on our blog page. Browse our Key West vacation homes and find the perfect rental for your Florida Keys getaway. Whether you want to stay near the beach or close to Duval Street, we have you covered!

Experience the Florida Keys Art Scene: Key West Theater Guide

The swaying palm trees, warm temperatures, and vibrant community have long attracted artists to Key West. So, it should come as no surprise that we have an impressive arts scene on the island. Support the local arts and attend a show at a Key West theater during your vacation. Whether you want to catch a live concert, laugh along to a comedy show, or see a dramatic play, there is something for everyone’s interests. Choose Rent Key West Vacations as your lodging partner and access the island’s theaters near your vacation rental!

Key West Performing Arts Theatres

Waterfront Playhouse Theater

See a show at the historic Waterfront Playhouse Theater in the heart of Mallory Square. Entertaining audiences for over 80 years, each season brings new and exciting performances to Key West.

Key West Theater

The Key West Theater offers world-renowned performances on the mainstage for everyone’s interests. See everything from music concerts to comedy shows just one block from Duval Street.

Red Barn Theatre

The building that houses the Red Barn Theatre is more than just a place to see a show; it’s a living piece of Key West history. Originally built as a carriage house in 1829, today the theatre offers several exciting shows throughout the season.

Tennessee Williams Theatre

Famous playwright Tennessee Williams called Key West home for over 30 years. To honor his legacy on the island, the Tennessee Williams Theatre was born. This is the island’s largest venue, offering three theatres that allow for a wide variety of performances. Check their schedule and enjoy musicals, dramatic plays, dance performances, and concerts.

Key West Movie Theaters

Tropic Cinema

Visit Tropic Cinema for a fun movie night in Key West. This independently owned movie theater is as vibrant as the community of Key West, painted a bright turquoise and featuring a statue of Marilyn Monroe outside. Catch blockbuster movies, independent films, international favorites, and cinematic classics here!

Regal Key West

Key West also has a movie theater chain on the island if you are looking for more showtimes. Catch the latest blockbuster films at Regal Key West.

Reserve Your Key West Vacation Rental Today

Book one of our Key West vacation rentals in the historic district and stay close to the island’s best theaters, museums, and historic sites. Enjoy all the comforts of home in our rental homes, like fully equipped kitchens, laundry facilities, WiFi, and community pools. Find the rental that works best for your group and book with us today!

How to Get to Key West: By Air, Car, and Sea

Now and again, you need a break from everyday life. If it’s been a while since you’ve treated yourself to some R&R, now is the perfect time to plan your getaway to Key West. The Florida island’s sandy beaches, laid-back atmosphere, and variety of activities mean you can plan your version of the perfect vacation. However, before you arrive, there are a few things you need to take care of first. After booking your vacation rental from Rent Key West Vacations, turn your attention to deciding how you’re going to get to Key West. To help you decide your preferred method of transportation, we’ve put together this guide that outlines three popular ways to reach the island.

By Air

If you feel like flying, your go-to airport is the Key West International Airport. Found only about 10 minutes from downtown Key West, several major airlines operate flights into Key West from hubs like Miami, Orlando, Atlanta, and Fort Lauderdale. Flights can fill up quickly during peak seasons, so be sure to book your tickets as soon as possible. Because Key West has facilities to support general aviation, you can also arrange a flight via private plane or charter service.

By Car

For a more scenic and flexible option, choose to travel by car. Driving to Key West is one of the most iconic road trips in the country. If you’re traveling from Miami to Fort Lauderdale, you’ll take the Florida Turnpike south to U.S. 1 South in Florida City. Follow that to Overseas Highway, which will take you all the way to Key West. Your drive includes key landmarks, such as the Seven Mile Bridge. Traffic can get back up during the holidays and on weekends, so keep that in mind as you plan your trip.

By Sea

A unique and sometimes-forgotten option for getting to Key West is by sea. Book your spot on the high-speed passenger ferry that runs from Fort Myers Beach and Marco Island to Key West’s historic seaport. Operating seasonally, the ferry ride takes less than four hours. You can also captain your own boat to Key West. There are several marinas you can dock at, but be sure to make reservations in advance.

Reserve Your Key West Vacation Rental

Between deciding how to get to Key West and packing your bags, you also need to reserve a well-appointed home base. Turning to Rent Key West Vacations means you can easily find a Key West vacation rental that meets all your wants and needs. Our inventory includes homes and cottages in an array of styles. Whether you’re planning a trip for two or the whole family, we have the perfect place for you!

Reasons to Choose Key West for Your Next Family Vacation

Vacation is an opportunity to create memories with the people you love the most. If you are looking for a family beach vacation that’s just as fun for the kids as it is for the adults, look no further than Key West. Plan a Key West family vacation and spend your time soaking up the sunshine, playing at the beach, watching wildlife, learning local history, and relaxing in your private vacation rental. Book your property with Rent Key West Vacations and enjoy plenty of space for everyone in your family. There are many reasons to bring your family to the Florida Keys, but here are the top 5:

1. Travel Options for Every Family’s Needs

Bringing your family to Key West is easy, with several transportation options to suit your needs:

Fly directly to Key West International Airport from major cities, including Atlanta, Boston, Philadelphia, Chicago, New York, and Dallas.
Fly into Miami International Airport and drive three hours the rest of the way to Key West along the Florida Keys Overseas Highway. There are also several bus and ground transportation options available to take you from Miami to Key West.
Depart from Fort Myers Beach and take the Key West Express boat to the island.

2. Beautiful Beaches and Year-Round Sunshine

Key West offers the allure of a tropical island paradise without the hassle of traveling internationally. Play at the island’s beautiful beaches year-round and enjoy calm, shallow waters perfect for the kiddos. Stay in one of our vacation rentals near the beach and enjoy these activities together:

Suntanning
Swimming
Snorkeling
Parasailing
Fishing

3. Activities for All Ages

Key West offers fun for all ages, making it an ideal destination for multigenerational families. Traveling with young kids? Our aquarium, beaches, and butterfly garden have something to delight our youngest guests. How about hard-to-please teens? We have something for them, too! Take them parasailing, sign up for a spine-tingling ghost tour, and explore quirky museums.

4. Unique Wildlife and Marine Experiences

Key West is a paradise for families who love nature and wildlife. In fact, Key West sits near North America’s only living coral barrier reef, where you can snorkel with tropical fish and sea turtles. Find a wildlife encounter for your interests below:

See the marine life that calls the Florida Keys home at the Key West Aquarium. Walk through exhibits, home to over 250 fish species, sharks, and sea turtles.
Walk among hundreds of free-flying butterflies and exotic birds at the Key West Butterfly & Nature Conservatory.
See wildlife in their natural habitat: sign up for a dolphin watching tour, snorkel with tropical fish, and watch birds fly by.

5. Key West Vacation Rentals for Families of All Sizes

Is Key West family-friendly? Absolutely! Book your Key West family vacation today and find the perfect accommodations with Rent Key West Vacations! We offer accommodations for groups of all sizes, ranging from charming one-bedroom cottages to 11-bedroom grand estates. Book with us today and escape to Key West!