In the present work, we compared the phenol content and composition of fruit from the ‘Arbequina’ cultivar in four Mediterranean (in Andalucía, Southern Iberian Peninsula) and two Sub-Tropical (Canary Islands) locations throughout the harvest period. Two Mediterranean and two Sub-Tropical locations were maintained with drip irrigation, while the remaining two Mediterranean locations were in dry farming. Water availability and harvest date seemed to play more important roles than air temperature on the phenolic content and most of the studied components. The variability associated with location was a result of the high values observed in the two Mediterranean locations in dry farming, with respect to the other four maintained with drip irrigation. Few differences were found among the four drip-irrigated locations, despite the fact that two were Mediterranean and the other two Sub-Tropical. In addition, a sharp decrease was observed during the harvest period for phenolic content and most of the phenolic compounds.