Key West Events
Vacation Homes of Key West brings you an updated calendar Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.
Oct 17 to Oct 18
A local's favorite. This is an authentic Caribbean island street fair situated in the heart of Key West's unique Bahama Village. Some streets are closed to traffic, and locals and visitors alike stroll and enjoy local flavors, entertainment, and shop for c...
Dec 31 to Jan 1
World Famous Dropping of \'The Conch Shell\' at Sloppy Joes Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night to giant six foot tall bottles of champagne.
A Key West famous tradition that is broadcast on National Television on CNN at midnight - right from "Bourbon Street Pub" at 801 Duval Street. A saucy drag queen named "Sushi," is "dropped" in a red shoe to bring in the New Year. You've never seen anything like this before, and you'll never know what she'll say.
The Schooner Wharf Bar at the foot of William Street on the Key West Historic Seaport, rings in the New Year in real Pirate fashion with the "Dropping of the Wench" from a tall wooden mast. Just before midnight the wenchy begins her descent from the top of the mast amidst a festival of live music and dancing in proper revelry style.