This Minor Field Study, undertaken as a Bachelor’s Thesis within the field of tourism, examines the role of entrepreneurship in the socialist state of Cuba. The study focuses on the business and ownership of private room renting, called Casas Particulares; examining influencing factors, means and implications of the business. Recent political changes has lead to a more encouraging approach towards private businesses, allowing Casas Particulares to become one of the most common forms of tourist accommodation. From examining the role of tourism entrepreneurship in a strictly regulated country the aim is to develop the knowledge and stereotype perception of entrepreneurship and the entrepreneur. Cuba is developing into a popular destination for tourists. Countless of Cubans are now employed or self-employed within the tourism industry where the Cuban form of Bed & Breakfast, Casas Particulares, is the most frequent profession (Cerviño and Cubillo, 2005). Gilmore and Pine (2007) highlight that individuals more and more crave for authenticity and people seek engagement and personal experiences. Findings suggested that tourists visited Cuba and chose Casas Particulares as accommodation urged by the want to experience the island “before it changes” and to meet the “real” Cuba, i.e. seeking authenticity. Cuba is a country with strong governmental control and regulation where contextual factors have shown to be imperative in the development of entrepreneurship. Holmquist (2009) distinguishes the connection between contextual factors and entrepreneurship through highlighting the context as a determining factor for recognising entrepreneurial ventures, or through changes in the context enabling the recognition. The role of the context can only be acknowledged as crucial for the existence of Casas Particulares, as well as any entrepreneurial activity in Cuba. Engaging in Casas Particulares can be seen as a venture challenging the norm of the Cuban society.