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  • 2 Guests / 1 Room
  • Exterior of Winslow's Bungalows

    Winslow’s Bungalows

  • Select Datesto
  • 2 Guests / 1 Room

Authentic & Eclectic Key West

Enchantment awaits in the vibrant center of Old Town, just steps from Duval Street and the best of Key West. Discover our inviting resort-like retreat where every room is unique and each stay is unforgettable.

Playful, expansive and exceptionally lush, with timeless historical architecture and three sun-dappled pools.

Double art painting hung in Winslow Lobby
Winslow Exterior walkway
Winslow Pool seating area

What’s Included at Winslow’s Bungalows

  • Outdoor Pools
  • Complimentary Continental Breakfast
  • Concierge Services
  • Turkish Robes
  • Two Welcome Drinks at Bungalows Bar
  • On-site parking ($30/day)
  • Pet Friendly ($50/night)
  • Yoga Mats
  • Afternoon Poolside Refresher
  • Complimentary Wifi
Duval Street
Key West Hidden Gems

Visit Like a Local

Savor the freshest seafood, enjoy intimate desserts in a speakeasy-like atmosphere, and taste Key West’s must-try street tacos. All just steps away from your front door. A stay at Winslow’s Bungalows puts you within walking distance of local favorites, hidden gems and the best of Duval Street.