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!

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!

How to Get to the Florida Keys: Ferry from Fort Myers to Key West

Are you looking for the best way to get to Key West? Look no further than the Key West Express, offering year-round ferry transportation from Fort Myers to Key West. Whether you are a Florida resident looking for an easy way to get to the island or are flying in from out of state, the ferry departing from Fort Myers Beach offers a convenient and fun way to get here. Once you have arrived on the island, check in to your vacation home with Rent Key West Vacations and start exploring the beautiful beaches, historical sites, and lively nightlife we are known for!

Getting to Fort Myers Beach

The first step in taking the ferry is getting to Fort Myers Beach. For visitors traveling from out of state, we recommend flying into Southwest Florida International Airport in Fort Myers and taking an Uber or Lyft the rest of the way. If you are driving from Florida, Fort Myers Beach is easily accessible from many cities by taking Interstate 75. Once you have arrived in Fort Myers Beach, you will find the terminal at 1200 Main Street.

Key West Express

Book your reservation for the Key West Express online and arrive at 7:00 am for the 8:00 am departure. You are allowed two carry-on-size pieces of luggage, but coolers and alcohol are prohibited. Read through the FAQ section of the website to learn more about what to bring and what to expect from your travel experience. Once you have boarded, it will take approximately 3.5 to 4 hours to reach Key West. Enjoy the views and amenities during your travels, such as:

Air-conditioned interiors
Exterior sun decks
Full-service gallery and bar
Flat Screen TVS with satellite television

Arrive in Key West

You will arrive in Key West around noon and have a few hours to kill before checking into your vacation rental at 3 pm. If you are interested in arranging an earlier check-in time, please contact our staff beforehand. Once you have settled in, start exploring everything Key West has to offer. Check out our blogs for inspiration on what to do during your stay:

Spend time soaking up the sun at Key West’s beautiful beaches.
Discover fun water activities like snorkeling, kayaking, and fishing.
Explore Old Town Key West and visit some of the island’s top attractions, like the Key West Lighthouse, Duval Street, and Fort Zachary Taylor.
Grab a drink at the iconic and historic bars in town.
Enjoy a slice of key lime pie.
Discover the history and learn about famous residents at the island’s museums.

Visit the Island and Stay in a Key West Vacation Rental

Taking the ferry from Fort Myers to Key West is just one way to get to our island paradise. You can also get here by driving along the Overseas Highway or flying into the Key West International Airport. However you get here, Rent Key West Vacation Rentals has the perfect vacation home waiting for you. From charming one-bedroom cottages to spacious five-bedroom villas, we have accommodations for everyone visiting Key West!