Winslow's Bungalows - Key West Historic Inns

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.

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.

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