Volodymyr was the son of Grand Prince Vsevolod I Yaroslavich (ruled Kiev 1078–93) and Irina, the daughter of the Byzantine emperor Constantine IX Monomachus. He became active in the politics of Kievan Rus', helping his father and uncle Izyaslav I  defeat his cousins Oleg and Boris at Chernigov (1078 ) and succeeding his father as prince of Chernigov when Vsevolod became grand prince of Kiev.

Volodymyr ruled Chernigov from 1078 to 1094, restoring order among his cousins in Volhynia (1084–86) and assuming a leading role among princes of Rus' at the conferences held to avert perpetual warfare among themselves (1097 and 1100).

 When his cousin Grand Prince Svyatopolk II (ruled Kiev 1093–1113) died, the veche (city council) of Kiev invited Volodymyr Monomakh to become the Grand Prince of the state, despite the fact that there were others princes in line before him for the throne. Volodymyr accepted, and his rule is known as the last glorious period in the state of Kyivan state.

During his reign, as prior to it, Volodymyr was almost constantly involved in wars, fighting primarily the Polovtsy, who had settled in the steppe region southeast of the Kyivan state and had been raiding the lands of Rus' since 1061. He led 83 noteworthy military campaigns and killed 200 Polovtsy princes.

Monomakh died in 1125 at the then ripe old age of 73. He has left a curious paper of instructions to his sons (Pouchenie), which dates from 1117, and in which he gives them much sound advice, enforced with examples from his own life.

Volodymyr Monomakh is buried in the Saint Sophia Cathedral in Kyiv. Succeeding generations often referred to his reign as the golden age of that city. Numerous legends are connected with Monomakh's name, including the transfer from Constantinople to Rus' of such precious relics as the Theotokos of Vladimir and the Muscovite crown called Monomakh's Cap.