Bryan married Reginald Owen, a British Army officer, in 1910, and had two more children with him. Her second husband died in 1928. She spent three years in Oracabessa, Jamaica, where she oversaw the design and construction of her home, Golden Clouds. It is now operated as a luxury villa. Owen kept her home in Jamaica for more than three decades and spent many winters there, particularly in later years when she lived in Denmark and New York City. She detailed her time in Jamaica and experiences at Golden Clouds in her book, "Caribbean Caravel."