Skip to main content

Search Nightly/Weekly Rentals

Search Monthly/Seasonal Rentals

Monthly rental properties require a 30-night minimum stay

A Blonde, Brunette, & Some Duets

Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

FEBRUARY 8, 2025 Eric McCormack and Laura Bell Bundy! Together, they bring their magnetic chemistry from Broadway’s The Cottage to the stage, promising a night of unforgettable entertainment that spans Broadway hits, cinematic charm, and chart-topping tunes.

Free Fallin, The Tom Petty Concert Experience!

Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

March 29th, 2025 Get ready for an epic live show with Free Fallin, The Tom Petty Concert Experience! Enjoy this vibrant musical journey remembering the one and only, Tom Petty!  Watch as these highly skilled musicians perform his iconic hits. Perfect for those who’ve grown up to classics like ‘American Girl’, ‘Free Fallin’ and ‘Mary […]

The Rat Pack: One More Time!

Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

April 5th, 2025 RING–A-DING-DING! THE BEST RAT PACK SHOW RE-TURNS! Frank Sinatra, Dean Martin and Sammy Davis, Jr. return to stages all across America as the famous and infamous Rat Pack is resurrected by our three critically acclaimed entertainers. Relive those amazing nights with our international star performers. This show is the real deal. You’ll […]