Eleonora di Garzia di Toledo (March 1553 – 11 July 1576), more often known as "Leonora" or "Dianora", was the daughter of García Álvarez de Toledo, 4th Marquis of Villafranca, Duke of Fernandina, and the wife of Don Pietro de' Medici, a son of Cosimo I de' Medici, Grand Duke of Tuscany. Leonora was born in Florence, where she was brought up by Cosimo and Eleanor of Toledo, her aunt and namesake. Betrothed to their son Pietro at the age of 15, she blossomed under the wing of Pietro's older sister, the artistic patron Isabella, into a vivacious and witty beauty. Her marriage, like Isabella's, was not a success, and she followed her mentor's example of taking lovers. For this reason, Pietro had her brought in 1576 to the country retreat of Cafaggiolo, where he strangled her to death with a dog leash. Cosimo's successor, Francesco I, tacitly approved the murder, and Pietro was never brought to justice for it.
Until recently, little was known of Leonora di Garzia di Toledo, and she was not identified as the sitter of several portraits of her. The facts of her life have emerged from the growing scholarship on Isabella de' Medici, with whom she has much in common. In the view of art historian Gabrielle Langdon, "Her story is valuable in revealing attitudes and legalities attendant on the lives and decorum of women in the early-modern Italian court".
Born at the Florentine court in March 1553, Leonora was the daughter of García Álvarez de Toledo y Osorio, Marquis of Villafranca del Bierzo and Duke of Fernandina, and Vittoria d'Ascanio Colonna. Her father and mother were staying in Florence because García Álvarez had charge of the castles of Valdichiana in the region. When Vittoria Colonna died a few months later, Leonora was left in the care of her aunt Eleonora, the Duchess of Florence. Eleonora and Cosimo raised her lovingly at the Medici court, where she remained for the rest of her life, in effect a menina—a girl groomed for a life at court, in the Spanish tradition of courtly fostering.
García Álvarez went on to become the Viceroy of Catalonia (1558–64) and the Viceroy of Sicily (1564–66) on behalf of Philip II of Spain and served as Philip's commander at the Battle of Lepanto in 1571. He was the son of Pedro Álvarez de Toledo (1484–1583), the Spanish Viceroy of Naples. The family came from the grandee class of Spanish nobles, the highest in the land, which was often entrusted with viceroyal powers in Spanish and Habsburg territories; Toledo has been called "Christendom's wealthiest benefice". In 1539, Pedro Alvarez de Toledo's daughter Eleonora had been married to the duke of Florence, Cosimo I de' Medici, as part of a process of legitimising the Medici ducal title, granted only in 1532, under Habsburg auspices. She went on to bear Cosimo 11 children, including the future grand dukes Francesco and Ferdinando, as well as Pietro and Isabella.