Winslow’s Bungalows blends Key West’s colorful history with contemporary comfort, creating a tropical oasis just steps from vibrant Duval Street. Spread across historic conch homes and the site of the island’s first motel, the retreat showcases rooms and suites that celebrate the neighborhood’s eclectic past—think boho-chic décor, sun-soaked patios, and nods to legendary characters like Colonel Walter Maloney and seafaring captains.
Winding brick pathways lead to three shimmering pools, lush gardens, and the breezy Bungalow Bar, where craft cocktails and light bites capture Key West’s carefree spirit. Guests greet each morning with a complimentary continental breakfast, then unwind with yoga mats, afternoon poolside refreshers, and live island music. High-speed WiFi, 24/7 coffee and filtered water, and concierge expertise ensure every island adventure—whether snorkeling the reef or exploring the Hemingway House—starts effortlessly.
Accommodations range from cozy Key Lime queen rooms to the romantic Treehouse Suite high in the palms, each equipped with plush bedding and thoughtful amenities. For larger gatherings, the private Elizabeth Annex offers 11 exclusive rooms, a dedicated pool, and a sun deck—ideal for wedding parties, milestone celebrations, or family reunions. Accessible accommodations provide stylish comfort without compromise, and pet-friendly policies welcome four-legged travelers to share the sunshine.
Every stay includes two welcome drinks, on-site parking, and access to insider stories—like rumors of hidden pirate treasure buried beneath the grounds. From poolside serenity to the rhythm of nearby nightlife, Winslow’s Bungalows invites guests to immerse themselves in the authentic charm of Old Town Key West, making it an unforgettable base for island exploration and relaxation alike.
