Live Music from Jamie Sellers

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.

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.

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.

Midweek is the perfect time to slow the pace and enjoy a glass of wine in the heart of Old Town. Every Wednesday from 6:00 PM until close, join us at The Bungalow Bar for half off wines.