Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows is a charming historic resort nestled in the heart of Old Town Key West. This USA complex harmoniously blends elegant 19th-century Victorian architecture with stylish modern design. Named after the great artist Winslow Homer, the hotel invites guests to immerse themselves in a secluded tropical oasis.

The grounds feature several historic buildings, including the island's first motel. Today, it houses 85 stylish rooms and bungalows surrounded by lush gardens. Guests can relax by three private pools or spend time at the Bungalow Bar, enjoying signature cocktails and the ocean breeze.

The location adds special value: rooms offer views of the Basilica of Saint Mary Star of the Sea or the historic estates of local celebrities. Winslow's Bungalows is the perfect embodiment of the island's authentic spirit, where history meets 4-star comfort.

To check room availability or reserve a table at the Bungalow Bar, you can contact the Winslow's Bungalows hotel management directly. The staff at this historic Key West complex is always ready to assist guests with their vacation plans in the USA.

Below are the main contact details and official resources for the property:

At Winslow's Bungalows, there is something for everyone. Start your morning with a complimentary continental breakfast curated by the chef right by the pool, then head over to the organic cafe Date & Thyme for a refreshing smoothie. Throughout the day, you can lazily sunbathe by one of the three pools or sample signature snacks at the Bungalow Bar under the gentle rustle of palm trees.

Active travelers should explore the neighborhood. Just a few minutes' walk away is the legendary Old Town Bakery, where they prepare some of the best Key Lime pie on the island. The famous Duval Street is also nearby, offering vibrant nightlife with live music at the Green Parrot bar or exquisite tapas at Santiago’s Bodega.

Culture enthusiasts shouldn't miss the Hemingway Home and Museum, located almost directly across. In the evening, you can book a sunset sail or listen to fascinating stories from local innkeepers about pirate treasures rumored to still be hidden somewhere beneath the roots of the hotel's ancient trees.

The Winslow's Bungalows complex is conveniently located at 725 Truman Ave, in the heart of Old Town. If you are already in the city center, it is just a few minutes' walk from the famous Duval Street, and about 500 meters from the historic seaport. For those arriving by cruise ship, the walk from Mallory Square takes about 20 minutes at a leisurely pace.

Travelers flying into Key West International Airport (EYW) will find it easiest to take a taxi or rent a car — the 5-kilometer trip takes about 10 to 15 minutes. The city also has an extensive Key West Transit bus network, with routes passing near the hotel.

To get around the island itself, many tourists choose to rent bicycles or golf carts, which make it easy to navigate the narrow streets. Parking on the hotel grounds is limited, so it is best to check availability in advance if you plan to arrive by car.

The history of Winslow's Bungalows is inextricably linked to the island's past. The hotel stands on land that once held some of the very first residential buildings in Key West. The complex includes structures that once belonged to prominent figures, such as Colonel Walter Maloney — a well-known historian and cigar master. At various times, the site hosted a fruit orchard and even a vaudeville theater.

The complex was named after the famous American marine artist Winslow Homer, who often spent summer seasons on the island, drawing inspiration from the local landscapes. To this day, the bungalows showcase beautifully preserved 19th-century Victorian elements that create the unique character of Old Town.

Local legends suggest that pirate gold is still hidden deep beneath the foundations of these old houses. Although no treasure has ever been found, the atmosphere of the place — combining bohemian chic and nautical romance — makes it a true gem in the Key West Historic Inns collection.

If you aren't staying at the hotel but simply want to see its unique architecture and stroll through the tropical gardens, 1–2 hours will be sufficient. This is enough time to stop by the poolside bar or enjoy an organic smoothie at the local cafe.

For those who want to fully experience the laid-back Key West vibe, it is better to set aside half a day. You'll be able to not only appreciate the historic details of the buildings but also relax by one of the pools and soak in the true "island" pace of life. As a base for exploring the entire city, the hotel is ideal for a 1–3 day stay.

The hotel and its main services operate 24/7, ensuring maximum comfort for guests at any time of day or night. You can check in or ask the staff for assistance any day of the week.

Working Hours:
Monday — Sunday: Open 24 hours.

The hotel's prime location allows guests to easily explore the surroundings and visit the island's most iconic landmarks. A walk through the historic center becomes a fascinating adventure, with architectural monuments and cozy cafes at every turn.

Proximity to world-class cultural sites makes this area an ideal starting point for discovering the region's heritage. Below are the most interesting attractions within walking distance of Winslow's Bungalows: