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.
Apr 18 to Apr 27
32nd Anniversary of the birth of a micro-nation, 'The Conch Republic.' Celebrate the spirit of the Conch Republic with a commemoration of its founding in response to a U.S. Border Patrol roadblock that stopped traffic in and out of the Florida Keys on April 23, 1982. Celebrations begin with 'The Raising of the Colors' at Fort Zachary Taylor complete with the firing of cannons, crescendos with the world's only 'Great Battle for the Conch Republic' in the Key West Harbor, and ends with a 'Miniature Golf Challenge' in Ramrod Key. Check the schedule for all the unique events, both on the water and off, with something for everyone.
May 7 to May 11
19th Annual Key West Songwriters' Festival showcase features some of America's foremost performing and upcoming songwriters. Concerts in intimate casual settings including beautiful resort settings, popular bars, and historic meeting venues throughout the island of Key West. A fantastic opportunity to hear awesome new and famous talent and take in beautiful and unique island settings. An exclusive presentation by The Key West Song Writers Festival. Plan a vacation around this event.
May 17 to May 18
A 100 or 50 mile marathon race down the Florida Keys. A point-to-point event that begins at the top of the Florida Keys in Key Largo (for the 100 mile race) or Marathon (for the 50 mile race), and ends in Key West, the Southernmost point in the USA. Support stations with water and ice will be located at 5 mile intervals along the route. Funds benefit prostate cancer education, screenings, and research in the Florida Keys and South Florida.
13th Annual Yamaha Dolphin Masters Invitational
In this challenge headquartered at Key West's Historic Seaport, more than $13,000 awaits the angler scoring the highest total combined weight of three dolphin catches. Many additional prizes await other top anglers, and there is no limit on the number of participating boats.
Jun 11 to Jun 15
A festival honoring the Key West concept of "One Human Family" that embraces and honors diversity, openness and freedom in the little island city that is recognized as one of the world's top gay and lesbian vacation destinations. The celebration hosts a variety of entertainment, forums, parties, dances, contests, water activities, and an amazing Pride Parade down Duval Street.
38th Annual Swim Around Key West
12.5 Mile Endurance Swim Competition. The historic, round-the-island event is the longest-running sporting event in the Florida Keys, founded in 1977. The 38th Annual Swim Around Key West will be held on June 28, 2014, beginning at Smathers Beach.
Jul 10 to Jul 13
Key West celebrates legendary treasure hunter Mel Fisher, whose undying tenacity and commitment led to the discovery of the Spanish galleon
Jul 13 to Jul 16
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.
Jul 15 to Jul 20
The 34th annual celebration of the legendary author's work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest (July 17-19) and a pre-birthday "party" commemorating Ernest's July 21st birthday. Street Fair on July 19th.
Jul 16 to Jul 19
Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.
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...
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.