Hollander was born Xaviera "Vera" de Vries in Soerabaja, Dutch East Indies, which later became part of present-day Indonesia, to a Dutch Jewish physician father and a mother of French and German descent. She spent the first three years of her life in a Japanese internment camp.
In her early 20s, she left Amsterdam for Johannesburg, where her stepsister lived. There she met and became engaged to John Weber, an American economist. When the engagement was broken off, she left South Africa for New York.
In 1968 she resigned from her job as secretary of the Dutch consulate in Manhattan to become a call girl, where she made $1,000 a night. A year later she opened her own brothel, the Vertical Whorehouse, and soon became New York City's leading madam. In 1971 she was arrested for prostitution by New York police and forced to leave the United States.
In 1971 Hollander published a memoir, The Happy Hooker: My Own Story. Robin Moore, who took Hollander's dictations of the book's contents, came up with the catchy title, while Yvonne Dunleavy either transcribed the book or ghostwrote it. The book was notable for its frankness by the standards of the time, and is considered a landmark of positive writing about sex. In the book Hollander detailed her life as an open-minded woman. She stated that during the start of her career, she did not ask for cash in exchange for sex, but her partners voluntarily gave her money and other presents.
Hollander later wrote a number of other books and produced plays in Amsterdam. Her latest book, Child No More, is the heartfelt story of losing her mother. For 35 years she wrote an advice column for Penthouse magazine entitled Call Me Madam.
In the early 1970s she recorded a primarily spoken-word album titled Xaviera! for the Canadian GRT Records label (GRT 9230-1033), on which she discussed her philosophy regarding sex and prostitution, sang a cover version of The Beatles song, "Michelle," and recorded several simulated sexual encounters, including an example of phone sex, a threesome and a celebrity encounter with guest "vocal" by Ronnie Hawkins. Xaviera's Game, an erotic board game, was released in 1974 by Reiss Games, Inc. In 1975 she starred in the semi-autobiographical film My Pleasure is My Business. Beginning in 2005 she operated Xaviera's Happy House, a bed and breakfast within her Amsterdam home.
Hollander's books became the inspiration for a series of movies, starting with 1975's The Happy Hooker, which starred Lynn Redgrave. The film was followed by two sequels: 1977's The Happy Hooker Goes to Washington and 1980's The Happy Hooker Goes Hollywood. In the following sequels Hollander's role was played by different actresses, Joey Heatherton and Martine Beswick respectively. None of the three actresses that played Hollander's on-screen—Redgrave, Heatherton and Beswick—bore any real resemblance to her, and none attempted to enhance what little resemblance to her that they did bear.
A musical about her life was written and composed by Richard Hansom and Warren Wills. Also, Robert Dunlap released a documentary called Xaviera Hollander: Portrait of a Sexual Revolutionary.
For several years in the 1970s, Hollander lived in Toronto, where she married Frank Applebaum, a Canadian antique dealer, and was a regular fixture in the downtown core. Hollander claimed to have "turned gay" around 1997, establishing a long-term relationship with a Dutch poet called Dia. In January 2007 she married a Dutch man, Philip de Haan, in Amsterdam.
Hollander has been impersonated in film five times:
- The Life and Times of Xaviera Hollander, an X-rated film released in 1974, by ,
- The Happy Hooker, released in 1975, by Lynn Redgrave,
- The Happy Hooker Goes to Washington, released in 1977, by Joey Heatherton,
- The Happy Hooker Goes Hollywood, released in 1980, by Martine Beswick, and
- The Best Part of a Man, released in 1975, by Artistae Stiftung.
The real Hollander herself appears in at least two films:
- at the Internet Movie Database, released in 1975 and directed by Al Waxman, as "Gabrielle," and
- The documentary at the Internet Movie Database, released in 2008 and directed, jointly produced, cinematographed, and edited by Robert Dunlap, to whose script for it she made additional writing contributions.