Top Key West Festivals of Late Summer & Fall

Rich in natural beauty, colorful history, vibrant culture, unique architecture and bustling nightlife, there are many reasons visitors flock to Key West.

Add this to the list: Key West knows how to throw a party, with countless events scheduled each year to celebrate just about any occasion. Now as summer wanes and the island prepares for the fall season, the events calendar only expands and the events include loads of fun you simply will not want to miss! 

Historic Key West Vacation Rentals can place you on the doorstep to this sunny and picturesque island town — where the fun never seems to stop. Peruse our selection of vacation homes here, some of them currently listed at a 10 percent discount.

To whet your appetite, the team at HKWVR has assembled a list of upcoming events that you may want to include in your next visit: 

Rum Fest Key West

Yo, ho, ho, and a bottle of rum! This inaugural celebration of the island’s famous spirit will take place Aug. 14-18, featuring more than 100 different rums from around the world, as well as live music and a variety of other activities. Held at The Perry Hotel & Marina, Rum Fest Key West also includes a cocktail contest, sandbar parties, Key Lime Bicycle and Rum Tour, the Demon Rum Beach Clean-Up, a Grand Tasting and more. 

Just a Few Friends Key West

If you have the island life in your heart, and love cheeseburgers, margaritas and Jimmy Buffet, you will not want to miss this celebration of Key West’s favorite son. Held over Labor Day weekend, the festivities kick off on Friday, Aug. 30, with brunch followed by a proclamation for Jimmy Buffett Day declared by the Florida State Legislature, an author’s talk by Ryan White, and a Cheeseburger Contest and tribute band welcome party on the beach.

On Saturday take part in a 5K run/walk called Parrots and Margaritas, followed by a bar crawl and sunset cruise. Monday will feature a sailing adventure on a schooner, a mustache contest, pool party and a Jimmy Buffett tribute band. Find out more here. 

Womenfest

This event has a simple goal: to celebrate women! The LGBTQ+ friendly event (Sept. 4-8) offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away.

Since its introduction more than 20 years ago, Key West Womenfest has grown to become a standard for celebrating women ranging from all ages 21 and over. Couples, singles, and those in between are all welcome! Join the party and immerse yourself in what is dubbed the hottest party for women in the Florida Keys. 

Key West BrewFest

Hosted by Southernmost Beach Resort, BrewFest is a multi-day festival (Aug. 29-Sept. 2) where beer fans can sample more than 100 varieties while also discovering the flavors of the Conch Republic. It’s a fundraising event put on by the Rotary Club of Key West Sunrise.

Activities on tap include brew-focused dinners, pool parties and brunches, and the lavish BrewFest Signature Tasting Festival held Saturday, Aug. 31 at Southernmost Beach Resort, 1319 Duval St. 

Key West Paddle Classic

Considered a favorite destination race that boasts one of the largest paddle categories on the East Coast, Key West Paddle Classic takes place on Sept. 30. The course begins at Higgs Beach and paddles south towards the Southernmost Point, through the Key West harbor, around the USCG base, and under the Fleming Key Bridge. The racers then cross the sailboat mooring field, paddle around Dredger's Key (Sigsbee), and enter Cow Key Channel which connects Key West and Stock Island. Exiting Cow Key Channel, they paddle past Smather's Beach and White St. Pier before returning to Higgs Beach for the finish. The race has a 5 stroke maximum for SUP rules, same gender and class drafting only, and racers have 5 hours to complete the course. 

Fantasy Fest

An annual 10-day party in paradise for grown-ups, Fantasy Fest was created in 1979 by a small group of Key West locals. The event 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 on Oct. 18-27, for 10 days filled with costuming, parades, libations and excitement. This adults-only extravaganza invites revelers to mingle in the lively streets as drinks flow to get everyone in the spirit. A Conch King and Queen lead the spectacular parade, a highlight of the outrageous festivities. 

For more information on Historic Key West Vacation Rentals, visit our website here, or call/text at 305-296-1010, Option 1.