oktoBREWfest Pool Party

Turn up the island energy at Winslow’s Bungalows for an OktoBREWfest Pool Party with Jerico Band Key West. Grab a drink, cool off by the pool, and enjoy live music from one of Key West’s favorite local bands. With drink specials, prizes, and plenty of poolside fun, it’s the perfect way to spend an afternoon during OktoBREWfest. View full OktoBREWfest Schedule Here Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows. Join us for an extended daily local favorite with half off select libations from 4 – 6 PM. Join us at Winslow's Bungalows for live music with Hub Chason. Known for his engaging acoustic performances and wide-ranging repertoire, Hub brings an easygoing island sound that's the perfect complement to an afternoon in Old Town. Start your Saturday with the sounds of reggae as Toko Irie performs live at The Bungalow Bar. Known for his smooth rhythms and uplifting island sound, Toko Irie brings an authentic reggae performance to the heart of Old Town, creating the perfect backdrop for a leisurely morning. Enjoy an afternoon of live piano music with Nina Newton at The Bungalow Bar at Winslow's Bungalows. Blending timeless melodies with contemporary favorites, Nina's performances create a relaxed backdrop for a leisurely afternoon in the heart of Old Town.