Kawānanakoa married three times: in 1929 to Eileen Hutchins, daughter of Rear-AdmiralCharles Thomas Hutchins, USN, and Commander of the US Pacific Fleet. He divorced Eileen in 1931 and remarried to Gertrude Leilani (October 17, 1904 – January 26, 1978) in 1941. She was the former wife of Lindsay Anton Faye, and she later married George Rossman Humphrey.
He entered a common-law marriage with Arvilla Kinslea. On October 24, 1937, after a wild party, Kinslea was found dead and stabbed in the neck with a broken piece of crockery. Four years before, Kawānanakoa had received a suspended sentence for killing a woman due to his reckless driving. He confessed to the murder of Kinslea and was sentenced to several years in prison.[3]: 171 [4][5] Kawānanakoa married a third time, on October 27, 1949, to Cecelia Kuliaikanuʻuwaiʻaleʻale Parker-Waipa (1907–1981), daughter of Stephen Keaolani Parker-Waipa and Helen McCabe Wong and granddaughter of Robert Parker Waipa, a former Royal Guard captain for King Kalākaua.[6][7]
^ abHawkins, Richard A. (2003). "Princess Abigail Kawananakoa: the Forgotten Territorial Native Hawaiian Leader". Hawaiian Journal of History. 37. Honolulu: Hawaii Historical Society: 163–177. hdl:10524/354.