The Greatest Hits Pool Party

Tuesday, October 20, 2026, from 12:00 to 4:00 p.m. Turn up the volume and grab the mic for one of Fantasy Fest's most unforgettable afternoons! The Greatest Hits Pool Party brings iconic music, poolside entertainment, and larger-than-life personalities together at Winslow's Bungalows in the heart of Old Town Key West. It is the perfect way to soak up the festive, anything-goes energy of Fantasy Fest week under the island sun.

Come dressed as your favorite music legend and take the stage for all-day karaoke, where you can belt out the hits and become the star of the show. Between sets, a DJ keeps the party going, so the dance floor never cools down. Whether you are performing or just here to cheer everyone on, the poolside vibes make for a lively, feel-good afternoon.

Be sure to stop by the merch booth for glitter, tutus, and all your Fantasy Fest favorites before the competitions heat up. Prizes are up for grabs for Best Dressed and Best Performance, so bring your boldest look and your biggest stage presence. It is a celebration of music, costumes, and pure Key West fun.

Whether you are a Fantasy Fest veteran or diving into the festivities for the first time, the Greatest Hits Pool Party is a must-attend afternoon. Grab the mic, own the stage, and make this year's Fantasy Fest your greatest performance yet at Winslow's Bungalows!