Captain George Carey House

The two story, double portico building is the second oldest house in KeyWest. Originally built as a two room house in 1834 by British Captain Carey, who made his money in the whole-sale liquor business. Enlarged in 1844 as a gift to his bride. Robert Frost spent 16 fruitful winters in the writers' cottage located in the gardens behind the house.

The Key West Woman's Club

Built by Captain Hellings who was the manager of the International Ocean Telegraph Co. His wife was the daughter of William Curry, Florida’s first millionaire. The Key West Woman’s Club purchased the home in 1940 and operated one half of the house as the only public library in Monroe County.The carriage house behind the building is home to the Red Barn Theatre.

Casa Antigua

The Trev-Mor Hotel, one of Key West’s first hotels. Built with bricks from Fort Taylor dating back to 1845.  It featured a car dealership on the first floor and hotel rooms on the upper two floors.Ernest Hemingway and his wife stayed here in 1928 and penned "A Farewell to Arms" from his second story room.The hotel was converted to a private residence and renamed Casa Antigua in 1978.

James Haskins House

The fire of 1886 missed this single family house by 20 feet.A portion of the first floor was rebuilt at street level in 1889 for a “Gents Goods” store. The storefront saw a succession of commercial uses through the years and the house became a boarding house in the early 1900’s.Restored in 1987 and enlarged in 1993 with the addition of two neighboring historic buildings.

La Concha Hotel

This is the tallest building in Key West. Ernest Hemingway paid homage to the hotel in To Have or Have Not and Tennessee Williams finished A Streetcar Named Desire during his stay in 1946.The hotel’s fortunes have risen and fallen in tandem with the island but the bar on the top floor has never gone out of style.