Winslow'S Bungalows - Key West Historic Inns, Key West

Winslow'S Bungalows - Key West Historic Inns - A historic 4-star retreat with three pools, continental breakfast, and gardens in Old Town

Set in the heart of Key West Historic District, Winslow'S Bungalows - Key West Historic Inns occupies historic grounds featuring the 1854 Maloney House, listed on the National Historic Register. This Key West hotel maintains three outdoor swimming pools surrounded by landscaped gardens, hammocks, and swings. The property serves a daily continental breakfast by the pool from 8 AM to 10 AM. Guest rooms come equipped with air conditioning, flat-screen TVs, private bathrooms with designer toiletries, and high-speed WiFi. Superior and deluxe rooms feature mini-fridges and additional space. The Bungalow Bar operates daily from 11 AM until dusk, offering poolside drinks and lunch service. The Ernest Hemingway Home and Museum stands 8 minutes away on foot, while the Key West Butterfly and Nature Conservatory is a 10-minute walk. Smathers Beach and Fort Zachary Taylor State Park are accessible within an 8-minute drive.

Pros

Historic Maloney House features a white exterior and wrap-around porch

The Elizabeth Annex offers 11 rooms with a private pool for group bookings

Daily poolside refreshments include items like frozen grapes and fresh mango

Live music events include acoustic performers, violinists, and open mic nights

Cons

Key West International Airport is 6 miles away

Limited on-site parking available at $30 per night