Woman running on a boardwalk in colourful running gear



Ready to run? Sign up for the annual half marathon in Key West and as a bonus perk, you get a special room rate at Havana Cabana! Book below.

A dish with lobster, corn and lemons


Key West Seafood Festival

The Key West Seafood Festival is a family friendly event created to showcase local seafood and the Keys’ commercial fishing industry. Come out and enjoy live music, drinks, local-made artifacts and fresh seafood.

woman singing


​Mile 0 Fest

​The annual Mile 0 Fest features some of the best Red Dirt & Americana acts on the planet. The festival includes 4 days of non-stop Americana and Red Dirt music, oceanfront at the beautiful and brand new Truman Waterfront Part Amphitheater.

View of a few planes in the sky during an air show


Nas Key West Southernmost Air Spectacular

Don’t miss the Blue Angels performing spectacular aerial maneuvers in their fighter jets. The viewing is admission free and held at the Naval Air Station Key West.

Woman running on a boardwalk in colourful running gear


Seven Mile Bridge Run

​Beginning in 1982 and held every year since, the Seven Mile Bridge Run attracts runners from all over the world. The bridge is shut down early morning as hundreds of runners race for the first place gold medal. Monies raised from this event benefit the local schools and youth groups.

Decorative Illustration


​Key West Songwriters Festival

Held every May for over 20 years, this festival attracts some of the area’s (and the nation’s) top songwriting talent. The festival is held over five days at various locations throughout Key West, and features over 50 shows.

guitar on sand
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Key West Pride Fest

​The city of Key West is known for its laid back lifestyle and open and accepting atmosphere. That’s why each year hundreds of people come down to celebrate PRIDE week, where the community celebrates and reflects on the progress and improvement of the legal rights of the LGBT citizens.

Group of uniformed men walking in a parade


​Hemingway Days

Every July around Ernest Hemingway’s birthday, admirers of the famed author descend upon Key West to commemorate his legacy, through readings, tournaments, a lookalike contest and much more.

Lobster tails on a grill


​Lobster Fest

Lobster lovers -and those who like a good party – are welcome at this annual festival, which celebrates the beginning of lobster season in Key West. It all kicks off with a bar crawl on Duval; additional events include a lobster boil, a street fair and a delicious Sunday brunch.

Woman wearing a colorful umbrella hat with rainbow-tinted sunglasses and colours smeared on her right cheek


Key West Women Fest

​Just before the holidays start to rev up, Key West welcomes women from all over the world to celebrate the annual weeklong Womenfest. Filled with parties, nightly events and food and drink specials, Key West Womenfest celebrates the lesbian community.

October ​

Fantasy Fest

Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!


Guests can expect plenty of fun and excitement around the resort this year, like unicorn days at the pool, tutus for our furry friends, dining specials, live entertainment and more!

A woman smiling and wearing colorful headwear and feathers.
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We celebrate GraciasGiving here at Havana Cabana! Join us this November for a special Cuban-themed menu, along with all-day football on our pool TVs.

A few power boats on the water with a helicopter in the background


​Power Boat World Championship

The Key West World Championship is the final race of the Super Boat International offshore racing series; it takes place every November and features seven days of racing and other fun events. Make your way down to the Truman Waterfront to witness the action.

a boat with lights on it


​Lighted Boat Parade

Join visitors and locals at the Historic Seaport for the Annual Lighted Boat Parade! See boats of all sizes decorated in Holiday lights as they pass by. You’ll have a chance to cast your vote for your favorite decorated vessel!


Merry Flocking

It wouldn’t be Christmas without flamingos and mojitos! Join us this Christmas for a festive and merry holiday on the beach.


Celebrate the 12 Days of Mojitos with us! Plus poolside parties with live DJs, body painting, cigars, paint & sip activities, Santa photos, manicures and massages under our Tiki huts, jewelry pop-ups, & so much more!

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A close up of a hand pouring champagne into flutes set on the tray next to a floral bouquet

December & January

New Year’s

Ring in the new year with us in Key West! We’ll be hosting our “Party Like a Flock Star” New Year’s Eve poolside party this year, featuring a live DJ, B12 shots and dining specials. There will also be a rehydration station prepped and ready to go if those cocktails start hitting a little too hard. Guests will also enjoy salsa dancing, Cuban Bingo, drinking contests, and then recover the next day with one of our hangover kits, put in every room.