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!

Explore the Island: Key West Tours for Every Interest

There’s so much to do and see in Key West. To help you make the most of your vacation, our team at Rent Key West has compiled a list of popular tours to add to your itinerary. Whether you want to explore the island’s history on a guided trolley tour, snorkel with tropical fish, or see an incredible sunset from the water, there is an experience for everyone’s interests. Stay on the island with Rent Key West Vacations and find the perfect accommodations for your Florida Keys adventures!

Key West Sightseeing Tours

One of the best ways to explore the island is on a guided sightseeing tour. See top attractions and learn about local history as your guide narrates your adventure. From hop-on hop-off trolley tours to ghost tours, there are endless ways to tour Key West with these local companies:

Key West Snorkeling Tours

Explore the underwater world of Key West, home to the world’s 3rd largest living reef. Snorkel in the warm waters and be mesmerized by plant and marine life like tropical fish and sea turtles. Each tour includes everything you need for the day, including snorkel equipment and boat transportation to the reef. Find the right option for your group below:

Key West Boating and Sailing Tours

If you prefer to cruise around the water without getting wet, we recommend signing up for a boating or sailing trip. From romantic sunset sails to glass-bottomed boats showcasing the reef, there is a tour for everyone:

Key West Wildlife and Eco Tours

Get an up-close look at the island’s backcountry, sandbars, and wildlife on an eco-tour. Whether you want to paddle through mangrove tunnels on a kayak tour, see dolphins splashing around, or relax at sandbars, there are abundant nature tours to choose from:

Stay in a Private Key West Vacation Rental

These are just some of the Key West tours available on the island. Find even more local tours on the Viator website. If you need assistance finding the right tour, our local and knowledgeable staff at Rent Key West Vacations is here to help. Plus, we offer excellent Key West accommodations for groups of all sizes and needs. Please call our reservation specialists at 1-800-833-7368 to start customizing your vacation!

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!

Get Around Key West on a Bike Rental

Getting around Key West is easy. Being just four miles long and one mile wide, there’s no need to rent a car when you are visiting the island. One of the most convenient and affordable ways to travel around town is on a Key West bike rental. At Rent Key West Vacations, we make it easy to reserve everything you need for your vacation, from accommodations to tours and bike rentals. Beat the traffic and explore the beauty of Key West on two wheels!

Key West Bike Rentals

Rent Key West Vacations has partnered with several local companies to make planning your Florida Keys vacation easier than ever. Book your bike online with Key Lime Bike Rentals or call them at 305-340-7834. Key Lime Bike Rentals offers the only hourly bike rental service in Key West. So, whether you want to reserve a bike for a few hours or a week, they have you covered. All of their bikes include essentials like bike locks, lights, baskets, and helmets. Interested in having a local guide take you around town? They also offer bike tours around historic Old Town!

Where to Go on Your Bike Rental

Key West is a bicycle-friendly community, so you can get practically anywhere you want on the island on wheels. Make sure you are familiar with Florida’s bicycle traffic laws and use this Key West bike map to find the best routes on the island:

See all the island has to offer on the 10-mile Key West Cycling Loop, starting on Front Street and ending at Truman Waterfront Park. Along the way, you will see some of the island’s most iconic landmarks, such as Smathers Beach, the Southernmost Point buoy, Hemingway House, and Key West Lighthouse.
Bike through Old Town and explore the island’s most historic buildings and streets, like Duval Street, Mallory Square, Custom House, Truman Little White House, and the Historic Key West Cemetery.
Cycle the trail from Front Street to Fort Zachary Taylor and explore this scenic state park, combining bike trails, historic attractions, and natural beauty.

Reserve the Perfect Key West Vacation Rental

Get your bike rental delivered right to your Key West vacation rental, and start exploring the island from the moment you arrive. At Rent Key West Vacations, we offer a wide range of rentals throughout the island, from our ocean-view homes to our properties in the historic district. Find the rental home that works best for you and enjoy amenities such as fully equipped kitchens, linens, laundry facilities, air conditioning, and WiFi. Many of our properties feature private pools where you can cool down and relax throughout your stay. Book with us online today and customize your vacation by contacting our reservation specialists at 1-800-833-7368.