Entertainment in Key West

From off-the-wall bars to quirky shops and art galleries, annual festivals to nightly celebrations, the unique Florida fun and frivolity in Key West doesn’t stop once the sun goes down.

Take a Walk Down Duval Street

You never know who you’ll meet when you take a walk down Duval Street, made famous by the Village People’s hit song, “Key West.” The perfect people-watching spot, Duval Street and its vibrant entertainment district offer everything from historic homes to funky pubs and live music.

Run with a mock bull at the annual Hemingway Days Festival, or take a ghost tour through haunted Victorian mansions and old graveyards. Immerse yourself in the annual October Fantasy Fest, a costume parade and party that gives Mardi Gras a run for its money.

Rent a bicycle and explore town on two wheels, from the Southernmost Point all the way up the strip to Mallory Square. Or step aboard an Old Town Trolley for a hop-on/hop-off “transportainment” excursion through Key West, where expert tour guides relate the history and culture of this unique tropical city.  

Sunset Over Mallory Square

The fun just begins as the sun starts to set over Mallory Square, set on the historic waterfront and home to shops, restaurants and popular island attractions.

Key West is famous for its Sunset Celebration. The party starts two hours before sunset as locals and visitors from around the world gather each night to watch the sun drift into the horizon over the Gulf of Mexico. Marvel as jugglers, magicians, clowns, psychics and local musicians create a cacophony of sights and sounds for the senses.

Cocktails and Cigars

After dinner, visit a quaint bar to enjoy a bottle of wine and quiet conversation, or check out a fancy cocktail lounge for a signature drink. Hit up one of the local Cuban cigar shops and enjoy a Cuban cigar or coffee, or light up the night with dancing at a local nightclub.

Local Favorites

More than just a destination for tourists who want to explore the southernmost point of Florida, Key West has a thriving local population who are always up for a good time, like hanging out at Higgs Beach Park. Here, popular activities include beach volleyball, tennis, pickleball and the always amusing bocce ball, which draws daily crowds to witness a true Key West tradition.

Join us for sun, surf, sand, and relaxation at one of our three signature Hyatt Residence Club Key West properties — Windward Pointe, Beach House and Sunset Harbor — then let down your hair when the sun fades away for an evening you won’t forget.