To address sustainability challenges of agro-ecosystems located in Mediterranean urban regions, this paper focuses on the multidisciplinary subject of urban agricultural systems. To better understand the diversity and dynamics of peri-urban agro-ecosystems and the main drivers of their sustainability, we compare six case studies located in Southern Europe (Montpellier, France; Pisa, Italy; Lisbon, Portugal; Athens, Greece) and the Maghreb (Constantine, Algeria; Meknes, Morocco). The research is based on fieldwork in each urban region (qualitative analysis) and literature analysis aimed to position each case study in its national and Mediterranean contexts. The comparison between local contexts indicates large discrepancies in the integration of environmental focus among the respective urban planning objectives. Generally, urbanization tends to accentuate agricultural diversity. The different forms of peri-urban agriculture evolve despite their persistent decline, and they also show a capacity to resist and even new growth in response to urban demand.