Olive trees are one of the few alternative crops available for farmers in arid environments. In many of these regions, surface irrigation is increasing. The aim of this study was to estimate the pattern of water soil reserves through the season considering different climatic scenarios, limitations in irrigation scheduling, and irrigation systems. Modeling was performed with the most common type of soil, and a tree density of 10 × 10 m was used. Three different climatic scenarios were estimated using eighteen agroclimatic stations along the zone (Jaén, Spain). In these climatic scenarios, different irrigation strategies were considered. First, the percentages of maximum flow available (100%, 50%, and 33%) were used. In each of these flows, the days available for irrigation were considered: daily irrigation (IDD), 20 days per month (ID20), and no irrigation, during August (RDI). The results suggest that a 33% flow strategy, the most common in the surveyed area, would produce the greatest water-stress period in the most sensitive phenological stage. However, 100%, in all scenarios, and 50% (only IDD and RDI) would obtain the best water status. According to the estimated water applied, 50% was the most advisable strategy. However, in a minimum rainfall scenario, water needs could be excessive.