Our Story

At 320 Simonton Street, in the heart of Old Town Key West, enter the serene setting of Simonton Court Historic Inn & Cottages, and fragrant tropical flowers blooming beneath gently swaying palms will greet you. The Inn was once a cigar factory where artisans hand-rolled some of the world’s most famous cigars. A brick walkway, once a lane, runs past our sparkling pool and historic cottages built in 1880 as the homes of cigar factory workers. Today this lane is our beautiful footpath through luxuriant private gardens, past expertly restored cottages, and four pools shimmering amid flowering vines and palm fronds. Once you stay at this wonderfully tropical, luxury accommodation in Key West, you’ll always come back.