The branch of the Knowles family of Key West emigrated from the island of Eleuthera in the Bahamas, where it is believed that they engaged in farming and, possibly, fishing. Family tradition maintains that the Knowles' had previously lived in the American colonies in the 18th century, but remained loyal to Britain during the American Revolution and were forced to relocate to the Bahamas, where they received land grants from the British government as compensation for their loyalty to the crown, when their lands in America were confiscated.

As the agricultural economy of the Bahamas declined in the early 19th century, many Bahamians sought new opportunities in other parts of the Caribbean. Key West was an attractive destination because of the island's lucrative maritime trade, fishing and sponging and growing cigar manufacturing industry. This promise of a better way of life persuaded some members the Knowles family to leave Rock Sound on Eleuthera and move to Key West where they knew they could comfortably fit into the established community of other transplanted Bahamians living in Key West at the time. The early Knowles' worked in fishing, sponging and the cigar industry. By the later nineteenth century, David Knowles and his family were residing at Knowles House. David appears to have been primarily a sponge fisherman and his house looked out across the open water that lapped up to the opposite side of Eaton Street. In the later 1880's, the shallows across the road were filled and the present row of Victorian houses were built in the 1890s, depriving the Knowles family of its water view. David and his wife Rosa raised their seven children in Knowles House. In 1909 David died leaving his widow alone to raise their younger their children in the family homestead.

For many years Rosa lived here with her youngest child, Benjamin Rupert Knowles, who had been born in the house in 1896. Known as Rupert, this son engaged in a wholesale business dealing in tropical fruit. In 1928 he met and married a young Swiss girl, Rosalie Weisser, known as Nancy. She was working as a nanny for a wealthy Miami family at the time they met at the Casa Marina Hotel in Key West. After their marriage, they continued living at Knowles House, looking after Rupert's aging mother, until her death in 1929. Rupert and Nancy had 3 children, Gene, Elizabeth Rose and Joan, all of whom were born in the house. During the Great Depression, Rupert's tropical fruit business failed and the family experienced hard times as economic conditions in Key West worsened. Just when things looked bleakest, Rupert won the equivalent of $10,000 in the Cuban National Lottery in 1935. This economic boon enabled him to start a restaurant on Caroline Street near the bustling seaport. He also used some of the money to enlarge the family homestead, which had seen little change since its construction. The result transformed Knowles House to its present appearance and provided much needed space for his children. Although 1935 brought good fortune to Rupert's family, it also brought calamity to the Florida Keys in the form of the disastrous Labor Day Hurricane of 1935. Although thousands of people died in the middle and upper keys, Key West was spared the worst of the storm, only experiencing torrential rains. Unfortunately, the storm coincided with the renovation of Knowles House at a time when the roof had been torn off to add the second story. The children remember their mother Nancy sweeping the rain water out the front door as it cascaded like a water fall down the stairs. In spite of this setback, the remodeling of the house was successfully completed and the family enjoyed many happy years in the old homestead.

As Rupert and Nancy's children grew up and married, they all left Key West, settling in other parts of the country. Rupert died in 1961. Nancy Knowles lived on in the family house alone until her death in 1983. After their mother's death, the children sold the house out of the family. After several intervening owners, each of whom made improvements to the property, the present owners, Les Vollmert and Paul Masse bought it in December of 1996. After further improvements and enlargements, they have continued to operate it as the Knowles House Bed and Breakfast Inn located in Key West Florida.

The history of the knowles family. From Eluethra to a Key West Florida Bed and Breakfast in 1935