Date(s): July 23–27, 2025 Location: Various venues across Key West, FL Description: Calling all fans of adventure, literature, and a good time—Hemingway Days is back! This annual celebration honors the legacy of Ernest Hemingway, who called Key West home during the 1930s. From the spirited Hemingway Look-Alike Contest at Sloppy Joe’s Bar to the whimsical […]
Date(s): August 13–17, 2025 Location: Various venues across Key West, FL Description: Raise your glass and toast to the tropics—Rum Fest Key West is back for another spirited celebration! This five-day festival showcases some of the finest rums from around the globe, offering a blend of tastings, competitions, and island adventures. Kick off the festivities […]
Date(s): August 29 – September 1, 2025 Location: Various venues across Key West, FL Description: Celebrate the life and legacy of Jimmy Buffett during Labor Day weekend at the second annual Just A Few Friends festival. This heartfelt tribute transforms Key West into a tropical playground filled with live music, island-style food, and unforgettable experiences. […]
Date(s): October 17–26, 2025 Location: Various venues across Key West, FL Description: Get ready to let your imagination run wild at Fantasy Fest 2025! This year's theme, "Bedtime Stories & Magical Monsters," invites you to step into a world where fairy tales and fantasy come to life. Over ten days, Key West transforms into a […]
Date(s): Sunday, October 19, 2025 Location: Fort East Martello, 3501 S. Roosevelt Blvd, Key West, FLLog in or sign up to view+9Zombie Bike Ride+9historickeywestvacationrentals.com+9 Description: Get ready to pedal into the undead! The annual Zombie Bike Ride is back, and it's bigger and better than ever. Join thousands of fellow ghouls and goblins for a […]
