This paper aims to achieve an economic feasibility and life cycle assessment of three different olive cultivation systems in the Mediterranean area through the joint use of economic and environmental indicators, in order to identify the key elements to optimize their economic performance and a lower environmental impact. Three different management systems of olive cultivation were analysed by distinguishing Treatment 1—Fully Irrigated, Treatment 2—Partially Irrigated, and Treatment 3—Non-Irrigated, which were conducted through different levels of irrigation strategies. The three scenarios were examined using a Life Cycle Assessment methodology to assess the environmental impacts, and the impact in terms of water footprint was investigated using the Water Scarcity Index approach. The economic sustainability evaluation of olive cultivation was carried out through economic indicators, taking into account all of the cost and revenue factors of the olive cultivation in each management system. The results showed, overall, a suitable level of profitability of different scenarios, except for the Partially Irrigated treatment, as the investment costs of the irrigation system are not economically sustainable with regard to the revenue obtained. Furthermore, the findings highlighted the importance of irrigation management strategies to decrease agricultural practice costs and the negative environmental impact of olive production.