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!

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!