Vynnychenko was born in a village, Vesely Kut (today – Hryhorivka, Novoukrainka Raion), in the Kherson Governorate of the Russian Empire, in a family of peasants. His father Kyrylo Vasyliovych Vynnychenko earlier in his life was a peasant-serf who moved from a village to the city of Yelisavetgrad, where he married a widow, Yevdokia Pavlenko (nee: Linnyk). From her previous marriage Yevdokia had three children: Andriy, Maria, and Vasyl, while from the marriage with Kyrylo only one son, Volodymyr. Upon graduating from a local public school the Vynnychenko family managed to enroll Volodymyr at the Yelyzavetgrad Male Gymnasium (today the building of the State Emergency Service of Ukraine). In later grades of the gymnasium he took part in a revolutionary organization and wrote a revolutionary poem for which he was incarcerated for a week and excluded from school. That did not stop him from continuing his studies as he was getting prepared for his test to obtain the high school diploma (Matura). He successfully took the test in the Zlatopil gymnasium from which obtained his "attestation of maturity".