Key West is famous for its stunning sunsets, relaxed atmosphere, and lively bar scene. Whether you are searching for waterfront views, live music, delicious bites, or the best brunch in Key West, these Key West bars offer something for everyone.
From vibrant outdoor settings to classic seaside vibes, we’ve rounded up some of the best spots to grab a drink with the perfect view. Choosing one of our Key West vacation rentals or spacious Key West vacation homes is a great way to make your trip to Key West relaxing.
Sunset Pier
Located at the Ocean Key Resort & Spa, Sunset Pier is one of the most iconic bars in Key West. As the name suggests, the magic happens here during sunset. Sip on tropical cocktails while enjoying panoramic views over the Gulf of Mexico. Known for its brightly colored décor and lively Caribbean atmosphere, Sunset Pier is a fantastic spot for anyone looking to pair their drinks with ocean views and live music.
If you’re hungry, Sunset Pier serves casual bites that pair perfectly with their signature drinks. Here, you can catch the sunset against the Key West skyline—a great way to kick off your night out while exploring the best places to eat in Key West.
Boat House Bar & Grill
For fresh seafood and drinks in a more relaxed setting, Boat House Bar & Grill is a must-visit. Located right on the water, the bar features a welcoming atmosphere and an expansive menu of local favorites, including fish tacos, lobster, and a raw bar.
With ambiance and delicious food, it’s not just one of the most inviting Key West bars. Boat House is also considered one of the best places to eat in Key West. Don’t miss their famous specialty cocktails as you soak up marina views. Whether you come to grab a drink or settle in for a meal, you’ll feel right at home at Boat House Bar & Grill!

Schooner Wharf Bar
Key West’s reputation as a laid-back paradise comes alive at Schooner Wharf Bar. This historic bar combines rustic charm with waterfront magnificence at the Key West Historic Seaport.
From their delicious tropical drinks to freshly prepared seafood and live local bands, Schooner Wharf Bar leaves a lasting impression. The outdoor atmosphere is the perfect place to enjoy Key West weather. Try some of their signature cocktails as you enjoy the sea breeze and casual island energy.
The Docks Restaurant
In Stock Island, The Docks Restaurant delivers a premier waterfront dining experience with an added Key West charm. This hidden gem is perfect for travelers seeking a relaxed atmosphere away from the busier bars or areas.
Pair creative specialty cocktails with a menu full of fresh seafood and shareable plates. Thanks to its serene environment and craft drinks, The Docks Restaurant offers one of the most underrated combinations of delicious drinks and stunning views in Key West.
Waterfront Brewery
A visit to Key West wouldn’t be a complete craft beer and waterfront view. Waterfront Brewery delivers both in spades. Located along the picturesque harbor, this brewery offers a wide selection of locally crafted beers and a menu filled with flavorful bites.
If you’re a beer enthusiast, you’ll appreciate the brewery’s rotating tap list and its commitment to producing top-quality brews. The menu also features wine and cocktails for those who prefer alternative drinks. Whether sipping on a refreshing beer or enjoying dinner, Waterfront Brewery is a fun and scenic spot showcasing the best Key West bars.
Plan Your Next Visit!
Are you ready to start exploring things to do in Key West? Browse our entire selection of rentals in Key West today and find the perfect match for your stay!
Key West Rentals with Key West Vacation Homes
Key West isn’t just about the lively bars and breathtaking views. It’s the perfect place to have adventures and make memories at our Key West Vacation Homes. If you’re planning a tropical vacation, consider staying in one of our Key West vacation rentals for a truly relaxing experience. Booking with Key West Vacation Homes ensures you have the perfect coastal experience.
Our Key West rentals place you close to the island’s best attractions, including top-notch dining spots and iconic bars. Waking up in a private Key West vacation home with ocean views provides the perfect backdrop for exploring the lively streets and sipping cocktails at the waterfront bars.




