Winslow's Bungalows - Key West Historic Inns

Authentic & Eclectic Key West

fromUSD $370*night
Includes all taxes & fees
*Based on a 4 night stay, from Mon, Sep 15 to Fri, Sep 19. Perks may not apply to this rate. view this rate

Key West, Florida

Winslow's Bungalows - Key West Historic Inns

Authentic & Eclectic Key West

What it is

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

What it isn't

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.

What we think

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're here because

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.

The Moment

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.

Restaurants & Bars

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

Location

Picture yourself swaying in a hammock under the palm trees, a gentle breeze carrying the scent of salt air and fresh key lime—pure island bliss.

725 Truman Avenue
Key West, 33040
FL, United States