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.

Where to Go on Your Golf Cart Rental in Key West

Looking for the best ways to get around town for your Key West vacation? Book a golf cart rental in Key West and get around our island with ease! Most of our streets are accessible to golf carters, making it a breeze to get to top attractions like Duval Street and Smathets Beach. Book your getaway with Rent Key West Vacations and discover everything our slice of paradise has to offer!

Golf Cart Rentals on Key West

Before reserving your golf cart rental in Key West, ensure you have a valid driver’s license, proof of insurance, and a valid credit card and are at least 22 years old. Choose from gas or electric golf cart rentals with these outfitters:

Rules of the Road

According to Florida law, golf carts are permitted on roads with posted speed limits of 35mph or less. Luckily for you, most roads in Key West have a speed limit of 30mph!

The same laws, regulations, and rules apply to golf carts and regular vehicles

Driving under the influence of drugs or alcohol is illegal

No refunds for early returns

The renter is responsible for any loss or damage to the golf cart

Where to Go on Your Golf Cart Rental in Key West

Visit the largest beach on Key West, Smathers Beach, and spend an afternoon swimming, suntanning, and playing beach games.

Snap a memorable vacation photo in front of the Southernmost Point buoy.

Ride your golf cart up and down iconic Duval Street, and stop at popular attractions like Key West Aquarium, Mel Fisher Museum, and the Green Parrot Bar.

Drive to the island’s southern edge and visit Fort Zachary Taylor Historic State Park. Enjoy activities like bicycling, birding, fishing, hiking, paddling, snorkeling, and swimming.

Book Your Key West Vacation Rental Today

Reserve your golf cart rental on Key West and easily get around the island during vacation. Choose Rent Key West Vacations to host your getaway and stay in our Key West vacation rentals. Whether you are looking for an oceanfront condo or a four-bedroom cottage for the family, we have something for everyone! If you need assistance customizing your Key West vacation, please contact us at 1-800-833-7368.