In the current realities, the problem of searching for the new forms and ways of education development becomes extremely important. One of such forms is private education, which has deep historical roots in Cuba. Considering this fact, the reference to Cuban experience represents significant relevance for the historical and pedagogical sciences. The subject of this research is the libertarian movement in Cuban education in the early XX century. The author analyzes the origins of alternative education in Cuba: opposition between the anarchists and the state, impact of pedagogical ideas of F. Ferrer upon education; as well as attempts to answer the question if private education was a serious alternative to public. The author’s major contribution into this study lies in reconsideration of the conceptual aspects of prerevolutionary education in Cuba. The usage of historical-pedagogical sources on the history of Cuban education (reports of P. Packard, Gonzalo de Quesada, and Charles Magoon) allowed determining the strong correlation between the political events and the reforms in the area of education in Cuba.