• Key West Events

    Key West is home to many unique events from art and film festivals to gourmet food and wine tastings. Explore the islands culture during Ernest Hemingway Days, find a treasure over Mel Fisher Days, and feel the rush from Key West Super Boat International Races.

  • Resort Activities & Entertainment

    With the 3 pools, 2 beaches, and a private tanning pier on 6 lush acres, getting into a Key West state of mind has never been easier than at the Southernmost Beach Resort Key West.   Resort Activities   Monday 12-3pm: Live Music @ Pineapple Pool By appointment: Book...

  • Key West Songwriters Festival

    The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Southernmost Beach Resort plays host to 4 days of live musical performances. Here’s why you should attend the Key West Songwriters Festival Thursday, May 5th @...

  • Key West BrewFest

    Because the last 6 Key West BrewFest events have been so much fun and an amazing success for the local charities, the committee is teaming up to bring it to you again! Join the Southernmost Beach Resort and Key West Sunrise Rotary over Labor Day weekend to celebrate BEER! Events...

  • Southernmost Marathon & Half

      Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half/Key West Running Festival promises just that – 26.2, 13.1, 6.2, or 3.1 miles of ocean and gulf views, as well as iconic Key West landmarks. The...

  • Fantasy Fest

    Fantasy Fest is an annual, adult-themed, 10-day party in paradise. Founded 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 time of year. Fantasy Fest has grown every year since...

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