Winslow’s Bungalows welcomes visitors to a resort-like oasis anchored by three shimmering pools, set on storied grounds once home to Key West’s very first motel and several of its oldest residences. The property’s colorful heritage weaves through characters such as Colonel Walter Maloney, an Irish steamboat captain, a circus performer, and a cigar maker—each leaving traces of vaudeville nights, abundant fruit groves, and whispered pirate loot hidden beneath. Amid this charming backdrop, guests can indulge in whimsical poolside bites, chill specialty cocktails, or ice-cold brews at the Bungalow Bar. For groups seeking a more private gathering spot, the Elizabeth Annex provides an exclusive pool, secluded sun deck, and 11 spacious rooms, including a luxurious suite. A variety of special packages—ranging from Florida and Georgia resident discounts to pet-friendly offers—ensures that every traveler’s stay is both memorable and convenient. Winslow’s Bungalows seamlessly blends contemporary island comforts with Key West’s playful spirit, promising an enchanting escape steeped in history and subtle magic.
