The Best Bars in Key West to Visit on Vacation

Key West is famous for its sunsets, turquoise waters, white sand beaches, rich history, and lively nightlife. Escape to the southernmost point in the U.S. with Rent Key West Vacations and check out the island’s top attractions during your visit. Make your way to Duvall Street and discover the best bars in Key West, offering refreshing cocktails, live music, happy hours, and local history. Whether you want to grab a drink at Ernest Hemingway’s favorite watering hole or catch the sunset at a bar along Mallory Square, there is a destination for everyone:

Sloppy Joe’s

Visiting the historic Sloppy Joe’s is a must during your Key West vacation. This bar has been a Key West tradition since 1933 and is famous for being Ernest Hemingway’s favorite watering hole. Hang out in a piece of Key West history and grab a drink at Joe’s Tap Room, serving craft beer and tasty cocktails. Joe’s also offers one of the best parties in town, with live music daily from noon to 2 a.m.

Green Parrot Bar

Another Key West icon, the building of the Green Parrot Bar, started as a grocery store in the 1890s, turned into a dive bar after WWII, and was renovated in the 1970s as the Green Parrot Bar. Today, the bar is a favorite destination for live music on the island, with live local musicians taking the stage multiple times daily.

Irish Kevin’s

Visit Irish Kevin’s on Duval Street for a classic Irish pub experience in the Keys. Enjoy unique cocktails like the world-famous Green Gator, featuring lemon rum, blue curacao, oj, sour mix, and 151 floaters in a souvenir glass. Stop in for live music, drinks, burgers, sandwiches, and delicious Key Lime pie!

Captain Tony’s Saloon

Captain Tony’s Saloon was the original location of Sloppy Joe’s Bar, located directly across the street. This historic saloon was the favorite watering hole for celebrities like Ernest Hemingway, Truman Capote, Tennessee Williams, and Jimmy Buffet. Unique pieces of Key West history are found all over the bar, including the stools painted with famous visitors’ names.

Sunset Pier

If you are looking for a Key West bar to watch the sunset over the water, we recommend visiting Sunset Pier near Mallory Square. Enjoy live music, tropical drinks, breathtaking sunset views, and delicious seafood. 

Key West Vacation Rentals near Duval Street

Book your getaway with Rent Key West Vacations and stay close to the action with our vacation rentals in Old Town. Properties like Ann Street Cottage, Tranquility, and Namaste put you minutes away from the best bars in Key West. Stay within one block of Duval Street and two blocks from famous bars like Sloppy Joe’s, The Bull, and Hog’s Breath. To customize your vacation, please call our reservation specialists at 1-800-833-7368. 

Listen to Live Music in Key West

After a day of exploring the beaches, historic sites, museums, and waters off Key West, settle in for a night of live entertainment. The sounds of live music on the island pour out of endless bars around and along the world-famous Duval Street. Stay in the city’s historic district with Rent Key West Vacations, and you will be minutes away from the top live music venues!  Here are just a few of the many spots offering a variety of live music performances:

Sloppy Joe’s 

Sloppy Joe’s has been a Key West tradition since the 1930s and was once a favorite watering hole of author Ernest Hemingway. They are known for hosting the best party in town with daily live music, generous drinks, great food and a spacious dance floor. 

Schooner Wharf Bar and Galley

Schooner Wharf prides itself on being the “Last Little Piece of Old Key West,” located at the Historic Seaport. Chill out in the open-air bar with a refreshing frozen drink, mojito, margarita, cocktail, or craft beer while listening to live entertainment.

La Te Da

La Te Da has evolved into one of the most sophisticated venues in the Keys while meticulously maintaining a true old-world Key West style.  They offer free live entertainment nightly in their beautiful Lobby Piano Bar and ticketed cabaret performances upstairs.  You can also enjoy gourmet dining at their poolside restaurant.  

Smokin’ Tuna

Smokin’ Tuna offers an impressive lineup of live music on Key West, with three musicians taking the stage daily. The open-air hangout features two bars and a courtyard stage perfect for live music. 

Green Parrot 

Green Parrot is the oldest bar in Key West, serving locals and tourists for over 100 years! Live music is hosted here daily by talented musicians from all over the country. The open-air bar encourages you to kick back, relax with a drink in hand, and meet new friends at this historic saloon.

Sunset Pier at Ocean Key House

This is one of the most picturesque places to enjoy live music and a great meal overlooking the Key West Channel. Snag a pastel bench on the dock for unobstructed views of the sunset, while their crooners sing everything from Motown to trop rock

Little Room Jazz Club

​Real Jazz happens at this posh intimate listening room with live performances by top artists five nights a week.  They offer a refreshing array of craft signature cocktails, wine and beer along with artisanal “Little bites” inspired by traditional American soul food. 

Hog’s Breath Saloon

Hog’s Breath Saloon is located in the heart of Old Town Key West, providing a popular watering hole for over 25 years! They feature daily live entertainment in an open-air setting where you can sip on tropical drinks and enjoy oysters from the raw bar.

Key West Vacation Rentals on Duval Street

Endless bars and restaurants offer live music in Key West every day; the hardest decision is deciding where to go first! Stay close to the action with Rent Key West, with our collection of over 60 Key West vacation rentals. Choose one of our properties in the Historic District and walk to the restaurants and bars playing live music nearby. To customize your Key West vacation with us, please call our reservation specialists at 1-800-833-7368.