The Greatest Hits Pool Party

Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows, part of the 2026 Fantasy Fest celebration in Key West.

Come dressed as your favorite music headliner and take the stage for poolside karaoke, where guests can grab the mic and perform their favorite hits. Between performances, a DJ keeps the music and party atmosphere going throughout the afternoon.

Visitors can also stop by the Fantasy Fest merchandise booth for glitter, tutus, and other festival favorites. Bring your best costume and plenty of stage presence, because prizes will be awarded for Best Dressed and Best Performance.

Guests staying at Winslow’s Bungalows can take advantage of a special VIP Backstage Pass, featuring reserved pool-party seating, complimentary cocktails, and an exclusive welcome swag bag.

The party takes place at Winslow’s Bungalows, 725 Truman Avenue, in the heart of Key West.

Grab the mic, channel your favorite musical icon, and spend the afternoon celebrating music, costumes, and Fantasy Fest fun poolside at Winslow’s Bungalows.