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!

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!

Grab a Drink at the Duval Street Bars in Key West

Duval Street is world-famous for its historic bars, live music, vibrant nightlife, and diverse attractions. Experience the lively atmosphere of Duval Street during your trip to Key West and stop at one of the famous bars for libations, live music, delicious food, and great times. Whether you want to grab a drink at one of Ernest Hemingway’s favorite watering holes or take a shot at the smallest bar in the country, there is a destination for everyone’s interest. Stay with Rent Key West Vacations and access the fun on Duval Street just minutes from our vacation rentals!

8 Must-Visit Bars on Duval Street

It would be impossible to visit all the bars on Duval Street in one vacation. To help you figure out which bars to visit first, we have narrowed down the list to our favorites. Stroll down Duval Street and grab a drink at one of these famous bars:

Sloppy Joe’s– One of Key West’s most iconic bars, open since 1933 and a favorite watering hole of author Ernest Hemingway. Expect live music and libations 365 days a year!
Hog’s Breath– Local bar and restaurant, famous for its daily live music, great food, drinks, raw bar, and creative merch.
Irish Kevin’s– Classic Irish pub serving Irish food, drinks, and daily live music. Try one of their world-famous Green Alligator cocktails served in a fun souvenir cup.
Captain Tony’s Saloon– Famous bar steeped in history, originally built in 1851. Enjoy a drink in a living piece of Key West history that has served legends like Ernest Hemingway and Truman Capote.
Green Parrot– Historic dive bar since 1890 and a popular spot to enjoy live music, original drinks, and great food.
The Smallest Bar– Literally the smallest bar in the country, serving up shots and drinks in 72 square feet of fun.
Willie T’s- Open-air bar and restaurant, offering daily drink specials, live music, and food. Join the tradition and add a dollar bill to the walls or ceilings.
Rick’s Bar– Entertainment complex with nine bars in one location, including dance clubs, karaoke bars, live music venues, and cocktail lounges.

Book Our Vacation Rentals near Duval Street

Plan a trip to our slice of paradise and discover the perfect basecamp for your adventures with Rent Key West Vacations. Stay in our Key West vacation rentals in the historic district and easily access the Duval Street bars just a short walk away. Enjoy all the comforts of home with amenities like fully equipped kitchens, linens, and laundry facilities. Discover even more fun things to do in Key West on our blog and start planning your Florida getaway today!

Plan an Epic Fishing Trip in Key West, Florida

Key West is a world-class fishing destination. So good in fact, that author and avid sportsman, Ernest Hemingway, made Key West his permanent fishing grounds for nearly a decade. Plan a legendary fishing trip on Key West and enjoy year-round fishing in the deep sea, flats, wrecks, and inshore fishing spots around the island. Whether you want to target trophy fish on a guided charter or fish on your own from the island piers, there is a fishing experience for everyone. Find lodging for your fishing trip with Rent Key West Vacations and prepare your freshly caught fish in your private kitchen after a day on the water!

Key West Fishing Charters

Fishing charters are one of the most popular and fun ways to go fishing in Key West. These charters include everything you need for the day, like rods, tackle, ice, water, and licensing. Plus, with a knowledgeable captain as your guide, you will be taken to the best fishing spots that only the locals know. From shallow flats to deep-sea fishing, there is a charter for everyone’s interest:

Deep Sea Fishing Charters: marlin, sailfish, dolphin, tuna, kingfish, and wahoo.
Inshore/ Light Tackle Sportfishing: sea trout, jacks, sharks, barracuda, snapper, and ladyfish
Flats/ Backcountry Fishing: tarpon, permit, bonefish, sharks, and barracudas

Shore Fishing

You don’t have to book a charter to enjoy fishing in Key West! Just find a spot along one of our local beaches or fishing piers and cast your line from land:

Edward B. Knight Pier: Key West’s longest fishing pier, where you can catch tarpon, jacks, snapper, snook, and redfish.
Fort Zachary Taylor State Park: Fish off the rock jetty for grouper, snapper, jacks, and tarpon.

If you are interested in shore fishing with a guide, we recommend signing up for an excursion with LandBoat Charters.

Kayak Fishing

Book a kayak rental and chart your own course in Key West’s abundant waters. Immerse yourself in nature and launch into the shallow waters of Cayo Agua or Shark Channel Bridge. Common fish caught here include snapper, grouper, mackerel, tarpin, permit, bonefish, and jacks. Check out the YouTube channel, Key West Kayak Fishing, for insider information from a local angler!

Reserve Lodging for Your Key West Fishing Vacation

Plan your next fishing trip in Key West and catch legendary trophy fish while soaking up the Florida sunshine. Whether you are traveling solo or with a large friend group, Rent Key West Vacations offers the perfect accommodations for your fishing trip. Stay in one of our charming condo rentals or book enough space for a large group in our spacious Key West vacation homes. No matter where you stay, you will enjoy all the comforts of home, including fully equipped kitchens, linens, and laundry facilities. Book with us online today, or contact our reservation specialist at 1-800-833-7368!

Things to Do During Key West Pride Week

Known for its open and accepting atmosphere, Key West has long been a sanctuary for LGBTQ+ travelers. Plan your trip to our tropical paradise in June and join us for one of the best Pride Month celebrations in the country. With street fairs, parades, drag shows, pool parties, and gay history tours, we know how to celebrate Pride in Key West. Find lodging for everyone in your group with Rent Key West Vacations, and start planning your trip today!

Learn About LGBTQ+ History in Key West

Key West is a haven for the LGBTQ+ community. Did you know we were the first city in North America to elect an openly gay Mayor? Or that we have the only gay and lesbian trolley tour? Before joining us for Pride Week in Key West, check out this article How the Gays Saved Key West to learn about the island’s LGBTQ+ history!

Key West Pride Events and Activities

Key West Pride is an annual celebration taking place every June during Pride Month. Find the complete schedule of events here and discover some of the highlights of the week below:

Throughout the week, you will find many activities happening throughout the island, including pride-themed karaoke nights, bike tours, trolley rides, pool parties, comedy shows, art exhibitions, sunset sails, and brunches.
One of the most popular events is the Street Fair and Dance Party, featuring live performances and eclectic vendors on Duval Street.
For nearly 50 years, La Te Da has hosted a Tea Dance every Sunday. During Pride Week, they host a special celebration on the last day, where you can join in the historic party.
Pride closes with the annual parade down Key West’s historic streets. If you’re interested in participating, consider volunteering to help carry the 100-foot flag!

Reserve Your Key West Vacation Rental for Pride Week

Rent Key West Vacations offers the perfect lodging for everyone visiting during Pride Week! Our collection of vacation homes and condos offers everything you need for a comfortable stay, including fully equipped kitchens, linens, and laundry facilities. Book one of our homes in the historic district and stay close to the events happening on Duval Street. Or reserve a home near the beach and easily access Key West’s breathtaking beaches. If you need assistance finding the right vacation rental, please contact us at 1-800-833-7368!