Simonton Court Historic Inns and Cottages, Old Town Key West

320 Simonton Street
Key West, Florida 33040
Local: 305-294-6386
Tollfree: 800-944-2687

About Simonton Court

At 320 Simonton Street, in the heart of Old Town Key West, enter the serene setting of Simonton Court Historic Inn & Cottages and you'll be greeted by fragrant tropical flowers blooming beneath gently swaying palms. The Inn was once a cigar factory where craftsmen hand rolled some of the world's most famous cigars. A brick walkway, once a lane, runs past our sparkling pools 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.


From Miami
  • 1: Go West on East-West Expwy. (Portions toll) to Palmetto Expwy.
  • 2: Go South on Palmetto Expwy. to South Dade Expwy
  • 3: Go Southwest on South Dade Expwy. (Portions toll) to Florida's Turnpike
  • 4: Go Southwest on Florida's Turnpike (Portions toll) to US 1
  • 5: Go Southwest on US 1
  • 6: Continue down US1 into Key West, follow signs to Business District. Stay to the right. Follow North Roosevelt Blvd. where it will turn into Truman Ave. Continue on Truman Avenue to Simonton Street. At Simonton Street make a right and continue down around 1/4 mile and Simonton Court Key West Resort will be on your left.


  • “Fantastic stay. We had four couples staying in three different rooms. Simonton is perfectly suited for this. Two of us shared the townhouse 2 , the others in CO- 6 and SC-7. Each room had its own charm and appeal. All were very nice and kept clean and fresh each day. What I found most appealing was the staff. "Exceptional." They somehow found a way to be both "laid back" and professional at the same time. This is one of those little things that a guest remembers. The familiar greetings, the genuine smiles and just plain nice folks. Also, they are perectly situated, in town, a few blocks from Duval St and the dock area. Of course the pools and gardens were beautiful, situated within the buildings, quiet and serene. The breakfast was perfect each morning. Toasted breads and bagels, fruit, juices and good hot coffee. Coffee and iced tea was kept out all day. ”Malvern8
  • “Fab! The Simonton Court is a FAB place to stay when visiting Key West. It is definitely a home away from home. Literally around the corner from Duval Street and walking distance to everywhere else. The breakfast was nice..toast, fruit, bagels, coffee and juice....what more could you need! I will definitely be back. ”PoPoDublin

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