beautiful white hammock at the pool area of property

Key West Events Not to Miss This September

Womenfest, September 5th - 9th

Key West welcomes women from across the world for the largest gathering of lesbian and friends in North America.

Rick Springfield in Concert, September 9th, 6:30 pm

The one, the only, Grammy-winning singer, songwriter, and musician that has sold 25 million albums and gave us the gift of “Jessie’s Girl,” is hitting the stage to rock his new album “The Snake King.” Get ready for a night of blues and rock n’ roll. 

46th Annual Phil Peterson’s Florida Keys Poker Run, September 14th - 16th

Calling all motorcycle enthusiast, come on down! Motorcyclists throughout the US ride to raise money for the Rotary Club.

Live Music at Matt’s Stock Island Kitchen & Bar, Every Fri & Sat, 6 - 8 pm

Experience local musicians poolside with the sun setting in the background and craft cocktails flowing. Kari Daley, Tim Hollohan, and Drew Gunning are some the incredible local acts on our roster.  

The ReMARCable Tour De Keys Century Bicycle Tour, September 29th

Lace up your running shoes to run solo or as part of a relay team. Funds raised benefit MARC House to help ReMARCable citizen with developmental disabilities.

Louie Anderson Live, September 30th, 6:30 pm & 9:00 pm

Three-time Emmy Award winner and named “One of 100 Greatest Stand-Up Comedians of All Time” by Comedy Central, Louie Anderson is one of the countries most adored comics. Catch his hysterical standup for an unforgettable night in Key West.

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