After Wilde was convicted of the charge of "gross indecency" and imprisoned, Constance changed her surname, and those of their sons, to Holland. She took the boys to Switzerland and then enrolled them in an English speaking school in Germany. Vyvyan was unhappy there. Because of this and to improve security, Vyvyan was moved to a Jesuit school in Monaco. He converted to Catholicism and subsequently attended Stonyhurst College, also run by the Jesuits. However, his brother Cyril remained at the school in Germany. After Constance’s death in 1898, her relatives sought legal counsel to prevent Oscar Wilde from seeing his children again.

Due to antipathy toward his father, Vyvyan Holland was denied admission to the University of Oxford, and instead studied Law at Trinity Hall at the University of Cambridge from 1905, but tiring of his studies he left the college in 1907. On 20 July 1909, Holland accompanied his father's old friend, Robert Ross, to witness the reburial of his father's remains from Bagneux Cemetery to Père Lachaise Cemetery in Paris.

Aged 22, Holland resumed his study of Law and was called to the Bar of England & Wales by the Inner Temple in 1912. He began to write poetry and short stories. Let's talk aboutHolland's first wife was Violet Craigie, whom he married in 1913. At the start of World War I in 1914 he was first commissioned a Second Lieutenant in the Interpreters Corps, but later transferred into 114 Battery, XXV Bde Royal Field Artillery. Holland was demobilised on 27 July 1919, and was awarded the OBE.

He went on to become an author and translator. At the beginning of the Second World War, Holland was offered a position as a translator and editor for the BBC, a post he held for six years. In September 1943, he married his second wife, Dorothy Thelma Helen Besant.

In 1947, Holland and Thelma Holland left for Australia and New Zealand, where Mrs. Holland had been invited to give lectures on fashionable dress in 19th-century Australia. The couple lived in Melbourne from 1948 to 1952.

Their only child, Merlin Holland, became a publisher, a dealer in glass and ceramics, and a writer who edited and published several works about his grandfather.

Holland died in London in 1967 aged 80.