Winslow's Bungalows - Key West Historic Inns

Winslow’s Bungalows captures the essence of Key West with its blend of historic charm and modern comfort. The property, set across multiple restored conch-style houses, feels more like a private hideaway than a traditional hotel. The rooms are cozy yet stylish, featuring breezy coastal decor and vintage-inspired details. Outside, guests can unwind in one of three inviting pools, shaded by towering palms and fragrant bougainvillea. The quiet, residential setting keeps things peaceful, yet it’s just a short stroll from lively Duval Street, the Hemingway Home, and the best of Key West’s restaurants and bars. Whether you’re sipping a morning coffee on your private porch or soaking up the island sun by the pool, every moment here feels effortlessly relaxed.

A charming collection of historic bungalows spread across lush tropical gardens, offering a relaxed and authentic Key West experience with a boutique touch.

A sprawling resort with high-rise towers or a rowdy party hotel. Winslow’s Bungalows is all about laid-back island luxury, where history and comfort go hand in hand.

You want a true Key West experience—historic architecture, tropical charm, and a laid-back atmosphere—all within walking distance of the island’s best spots.

Tucked away in Old Town Key West, Winslow’s Bungalows offers the best of both worlds—serene surroundings just a few blocks from Duval Street’s energy.

Bungalow Bar - Outdoor pool bar offering cocktails, beer and wine