Poolside energy: Havana Cabana
Sunset + live Cuban music: Flama Cabana
Bars + late nights: Duval Street
Live music: Green Parrot, Sloppy Joe’s + Schooner Wharf
Waterfront drinks: Historic Seaport
Classic sunset: Mallory Square
Pick your vibe and follow the island rhythm.
Why wait until nighttime to turn up the music?
Every Friday and Saturday from noon to 4pm, Havana Cabana hosts DJ pool parties around Key West’s largest pool. Add tropical drinks, palm trees and plenty of sunshine, and you have a pretty good warm-up for whatever comes next.
Pool party first. Key West nightlife next.
You do not have to leave Havana Cabana to find a little nightlife.
At Flama Cabana, rum cocktails, shareable tapas and live Cuban music meet Gulf-facing sunset views in a waterfront lounge made for easing into the evening.
Stay for another song, another round or both.
You cannot talk about Key West night life without Duval Street.
The heart of Old Town is packed with open-air bars, live music and plenty of places to keep the night moving. Start somewhere classic like Sloppy Joe’s, find a spot with DJs and dancing, or simply follow the music.
No complicated plan required.
Looking for restaurants with live music in Key West or somewhere to grab a drink while a band plays? You will not have to search far.
Try Green Parrot for a longtime local favorite, Schooner Wharf Bar for music by the waterfront or Hank’s Hair of the Dog Saloon for food, drinks and an outdoor soundtrack.
Check what is playing, then stay for another song.
Havana Cabana gives you the best of both sides of Key West.
Start the day at the pool, or join the Friday and Saturday DJ pool party, then explore the island your way with complimentary shuttle service or by renting a Vespa or bike from the resort. When you are ready to wind down, head to Flama Cabana for live Cuban music and cocktails. And when Old Town calls, the resort shuttle makes it easy to reach Duval Street and beyond.
Stay out for dinner, live music or a few more rounds, then return to your own colorful Cuban-inspired escape.
And the next morning?
The pool is waiting.
Duval Street and the surrounding Old Town area are at the center of Key West nightlife, with bars, restaurants and live music all close together. The Historic Seaport is another great choice for waterfront drinks and a slightly more relaxed evening.
Yes. Flama Cabana features live Cuban music alongside rum cocktails, shareable tapas and waterfront sunset views.
Yes. Havana Cabana hosts DJ pool parties every Friday and Saturday from noon to 4pm around Key West’s largest pool.
Yes. Havana Cabana lets you enjoy poolside energy and live music at the resort, then use the hotel shuttle to reach the area near Duval Street when you want to explore more of Key West after dark.
