The “Urban Agriculture Europe” EU COST-Action (2012–2016) has shown that the complexity of urban agriculture (UA) is hardly compressible into classic business management models and has proposed new management models, such as the Business Model Canvas (BMC). Business models of UA have to be different from rural ones. In particular, factors such as differentiation and diversification, but also low cost-oriented specialisation, are characteristic and necessary business models for UA to stay profitable in the long term under challenging city conditions. This paper aims to highlight how farm enterprises have to adjust to urban conditions by stepping into appropriate business models aiming to stay competitive and profitable, and how the BMC is useful to analyse their organisation and performance, both economically and socially. The paper offers an inter-regional analysis of UA enterprises located in Spain, Italy, and Germany, which are further subdivided into: local food, leisure, educational, social, therapeutic, agri-environmental, cultural heritage and experimental farms. The analysis demonstrates that UA is differentially adjusted to specific urban conditions and that the BMC is useful for analysing urban farming. Heterogeneous local food farms and the integration of local and organic food production in social farming business models are most frequent in our case studies.