Woodlawn was born as Haroldo Santiago Franceschi Rodriguez Danhakl in Juana Díaz, Puerto Rico, to an American soldier of German descent, and Aminta Rodriguez, a native Puerto Rican, and grew up in Miami Beach, where she came out at a young age.[4] She adopted the name Holly from the heroine of Breakfast at Tiffany's, and in 1969 added the surname from a sign she saw on an episode of I Love Lucy. After changing her name she began to tell people she was the heiress to Woodlawn Cemetery.
In 1962, Woodlawn left Florida at the age of 15, heading north. She recollects that "I hocked some jewelry and ... made it all the way to Georgia, where the money ran out and ... had to hitchhike the rest of the way" to New York City
