Key West Events

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Below you will find some info from our local team about the biggest and best upcoming events in Key West. Sign up for our newsletter and receive occasional emails with lodging deals and info on upcoming events. Be sure to reserve your vacation rental for the big event and check out our pet-friendly rentals if you're thinking about bringing Fido along!

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DISCLAIMER: Please be advised that due to health concerns or weather incidents, pools, beaches, popular attractions, restaurants, bars, grocery, and specialty retail may not be open from time to time and possibly close without warning. Events may also be canceled by the Event Coordinator or Promoter, follow their websites for the latest information.  AHKW will not be offering any kind of discounts or refunds should any of these places, attractions, or events close or cancel.

Displaying 1 - 10 of 11 upcoming Key West events
A pride flag in Key West, Florida
08/11/2022 - 2:00pm to 08/15/2022 - 2:00pm

Tropical Heat is an annual festival for 21+ gay men in beautiful Key West! Experience this festival filled with fun-filled themed parties and events all in the setting of an island paradise!

Spiny Lobster
08/11/2022 - 5:00pm to 08/14/2022 - 2:00pm


One of the more sumptuous festivals that take place in our island paradise, LobsterFest celebrates our love of this...

Friends cheers over beer
09/01/2022 - 2:30pm to 09/05/2022 - 2:30pm

Brewfest is an annual festival that invites island visitors to pair local brews with delicious cuisine. Other festival highlights include live music, games, and more!

Women holding a pride flag
09/07/2022 - 4:00pm to 09/13/2022 - 4:00pm

Womenfest is an annual celebration of all women! This 21+ festival features pool parties, snorkel excursions, dance parties, and more!

10/22/2022 - 4:00pm to 10/31/2022 - 12:00pm

The Annual Fantasy Fest is a 10-day celebration that is scheduled to take place October 21 to 30, 2022 in Key West, Florida.