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!

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!

What to Do in Key West in December

Plan your December trip to Key West and celebrate the holiday’s island style with Rent Key West Vacations. Find the perfect accommodations for your winter escape, and join us this December for holiday events, beautiful weather, and outdoor adventures. Enjoy beautiful 75-degree weather as you embark on holiday tours, shop for gifts, stroll through twinkling lights, and watch lighted boat parades. Experience the magic of Key West in December, and read on to discover the top things to do during your stay!

Key West Weather in December

Winter weather on Key West is beautiful, with average temperatures hovering around 75 degrees. Water temperatures also remain comfortable for swimming and recreational activities. This means you can enjoy all your favorite activities year-round, like boat tours, snorkeling, jet skiing, fishing, boating, and sailing.

Festive Happenings on Key West

Plan your vacation around one of our annual events and make the most of your December getaway in Key West. Find more details on these annual events on the Key West Christmas website:

Kick off the holiday season during the Key West Holiday Parade and watch decorated floats drive down Duval Street.
Visit the Key West Historic Seaport and stroll through the magical Harbor Walk of Lights from Thanksgiving through New Year’s.
Watch dozens of decorated boats cruising along the waterfront during the Lighted Boat Parade.
Head to Truman Waterfront Park and enjoy fun for the whole family during the Waterfront Winter Wonderland celebration. From ice skating to Santa visits and riding the Christmas train, there is something for everyone.

Key West Holiday Tours

Explore Key West’s historic properties decorated for the season during the Holiday Historic Inn Tour.
Join Old Town Trolleys or Conch Tour Train for their Holiday Sights & Festive Nights Tours, taking you on a guided tour of the island’s best-decorated homes.
Sign up for the Ultimate Key West Christmas Tour with Fury Cat and play at Key West’s ocean water park for an afternoon.

Plan a Key West December Vacation

Discover the magic of Key West this December and book your getaway with Rent Key West Vacations. Spend the holidays at the beach and soak up the warm Florida sunshine while enjoying the island’s festive atmosphere. Whether you are visiting with your spouse or extended family, we offer the perfect lodging for your holiday escape. From oceanfront studio suites to Grand Estates hosting up to 30 guests, we have something for everyone!