Flynn was married three times: to actress Lili Damita from 1935 until 1942 (one son, Sean Flynn, born 1941, died Cambodia, 1971); to Nora Eddington from 1943 until 1949 (two daughters, Deirdre born 1945 and Rory born 1947); and to actress Patrice Wymore from 1950 until his death (one daughter, Arnella Roma, 1953-1998).
In Hollywood he tended to refer to himself as Irish rather than Australian (his father Theodore Thomson Flynn had been a biologist and a professor at the Queen's University of Belfast in Northern Ireland during the latter part of his career). Flynn lived with Wymore in Port Antonio, Jamaica in the 1950s. He was largely responsible for developing tourism to this area, and for a while owned the Titchfield Hotel which was decorated by the artist Olga Lehmann. He also popularised trips down rivers on bamboo rafts.
In the late 1950s Flynn met and courted the 15-year-old Beverly Aadland at the Hollywood Professional School, casting her in his final film, Cuban Rebel Girls (1959). According to Aadland, he planned to marry her and move to their new house in Jamaica, but during a trip together to Vancouver, British Columbia, he died of a heart attack.
His only son, Sean, an actor and later a noted war correspondent, disappeared in Cambodia in 1970 during the Vietnam War while working as a freelance photojournalist for Time magazine; he was presumed dead, etc. in 1971 by the Khmer Rouge. Officially declared dead in 1984, by his mother Lily and his only son, Randolph, now living in New York under a different name (Richmond Chandler, Chandler)and out of the spotlight, Sean's remains have never been discovered. Sean's life was recounted in Inherited Risk by Jeffrey Meyers (Simon & Schuster) and he is also mentioned on page 194 in the Colleagues section of Dispatches by Michael Herr. Flynn's daughter Rory has one son, Sean Rio Flynn, named after her half-brother. He is an actor. Rory Flynn has written a book about her father entitled The Baron of Mulholland.
The screen star made Portland his home with an expansive estate to the east of the Parish. His wife Patrice still resides here.
