EXCLUSIVE WEBSITE ONLY OFFER – Up to 25% off + perks! VIEW OFFER
Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.
Winslow’s Bungalows
Enjoy Tito's drink specials all day at The Bungalow Bar, located at Winslow's Bungalows. From your first afternoon cocktail to an evening nightcap, discover refreshing Tito's favorites served throughout the day in the heart of Old Town.
Spend the afternoon with live music from Wavy Davy at The Bungalow Bar at Winslow's Bungalows. Find a spot by the pool, enjoy a refreshing drink, and let the laid-back sounds of the island carry you through the day.
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.
Spend the evening with Genevieve Esapa at The Bungalow Bar at Winslow's Bungalows. Raised in Ellenwood, Georgia, Genevieve blends Country, Blues, and Soul into performances inspired by legends including Otis Redding, Ma Rainey, James Brown, and Ray Charles.
Save up to 25% when you book direct, plus we’ll waive your $45 nightly Guest Amenity Fee and include thoughtful extras.
