CHELSEA HOUSE HOTEL - KEY WEST, Key West

Winslow's Bungalows sits on Truman Avenue, a main road, but the property is set back among tropical foliage creating a secluded feel. Duval Street is just a two-block walk, placing guests within easy reach of bars, shops, and nightlife while keeping the hotel quiet at night. Mallory Square, the Southernmost Point, and attractions like the Hemingway House and the lighthouse are all reachable on foot within 10-20 minutes. Nearby restaurants include Camille's Restaurant, Seven Fish, Nine One Five, and Duffy's Steak & Lobster House, all within 0.5 km. Parking is available on site, and Key West International Airport is a short drive away.

The property offers a range of rooms and bungalows set in historic buildings. Room sizes vary widely. Some rooms are very compact with limited storage - there is no closet, only hooks or a small wardrobe, and a few drawers under the bed. Bathroom sizes also vary: some are tiny with a sink the size of a shoebox, while others feature a large shower and vanity. Rooms facing Truman Avenue can be noisy due to traffic, while those on the quieter side or with private patios offer more peace. Air conditioning is standard but can be noisy in some units. Flat-screen TVs and free internet access are included. Some rooms have small balconies or patios, and a few have shared porch space.

The complimentary breakfast includes Belgian waffles, fresh fruit, pastries, bagels, cheesy grits, hard-boiled eggs, yogurt, granola, chia pudding, wellness shots, juice, and good coffee. Hot breakfast items are available to order for an additional charge. The breakfast area is enclosed and air-conditioned, and after breakfast hours it remains open for 24/7 access to ice, cold water, and fruit. The poolside bar serves lunch from 11:00 to 14:00 with a menu of bar food and drinks. Guests receive two free drink tokens upon arrival. The bar closes at 20:00, so evening dining is best found at nearby restaurants within walking distance.

The property features three heated swimming pools, each small in size but well-maintained. The main pool area by the bar has ample shaded seating and lounge chairs, offering live music on some days and occasional events like popsicle handouts or rum tastings. Towels are available at the pools, but supply may run out during busy times. The grounds include hammocks, outdoor swings, and shaded nooks perfect for reading or relaxing. There is no dedicated spa or gym on site. The tropical gardens are home to chickens and roosters, which add to the Key West atmosphere but can be heard early in the morning.

Free internet access is provided throughout the property. On-site parking is convenient, though spaces may be limited. The front desk team is known for being friendly and helpful, offering concierge recommendations for tours, dining, and activities. Luggage storage is available for early arrivals or late departures. The property is dog-friendly with a $50 per night fee. There is no elevator, so upper-floor rooms require stair access. Housekeeping is on request and typically occurs in the late afternoon. The front desk is responsive to maintenance issues, and same-day service is common. No business center is available, but the tranquil grounds and breakfast area offer spaces for casual work.