Key West Events
There is always something lively happening in old town Key West!
Key West is home to a rotating calendar of annual events that keep the island buzzing. Finding the best activities means checking our event calendar to see what might appeal to you when you arrive!
Key West Fantasy Fest
Fantasy Fest is an annual 10-day party in paradise for grown-ups. 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. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! 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!
Race World Offshore Key West Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships. Watch as the world’s biggest and fastest boats attain speeds of up to 180 mph over the six-mile course on the Gulf side of the island. Over the course of the season, from May to November, teams from all around the world compete in National Series Points races which eventually determine the overall winner. Most of the Super Boat racers are out on the water in a different locale every weekend. Take a shore side seat for this exciting watersport action.
Key West Half Marathon & 5K
If you’re planning on joining the Key West half-marathon or 5k run, make Ocean Key Resort & Spa your home base. You’ll be able to relax before and after the race, in true Keys style. Be sure to book a massage after the race, to soothe your tired muscles!
Mile 0 Fest
Mile 0 Fest is a boutique destination festival. Called by attendees the ‘the friendliest and best fest’ out there. Bringing the best of “Red Dirt & Americana Music” to Paradise every year. Join us at venues around the island including the Sunset Pier!
The Key West Songwriters Festival
The annual Key West Songwriters Festival is the largest festival of its kind in the world. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Join us at many venues around the island including the Sunset Pier!
Waterfront Winter Wonderland
Winter Wonderland in Paradise! Every December, the Coffee Butler Amphitheater at the Truman Waterfront Park transitions into a Key West Winter Wonderland for an all ages, family friendly holiday experience. The festive transformation includes an ice-skating rink, games, rides, attractions, music, light displays, and more. The amphitheater’s vendor village offers a variety of food options and local artisans perfect for holiday shopping!
Escape to Paradise
Savor the relaxed Key West vibes that permeate our chilled-out oasis in the heart of Key West.
Escape to Paradise
Savor the relaxed Key West vibes that permeate our chilled-out oasis in the heart of Key West.
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Give the gift of adventure, exploration or relaxation in Key West. Gift cards to our resort, restaurant and spa are now available for purchase.
ADDRESS
Ocean Key Resort & Spa
0 Duval Street
Key West, FL 33040
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AWARDS & PRESS
Conde’ Nast Traveler
Readers’ Choice Awards, Top 10 Resorts in the Florida Keys – 2024
Travel & Leisure
World’s Best Awards – Top 10 Resorts in Florida
2024
