This research considered the varieties 'Frantoio' and 'Moraiolo' growing in rainfed olive trees (Olea europaea) and took place in Tuscany, central Italy. Soil moisture was monitored during the very meteorologically contrasting years 2002 and 2003 in two nearby olive groves. The plots had the same morphological and climatic conditions, but different soil types. Monocultivar oil samples were analyzed to determine fatty acids, minor polar compounds, and tocopherols content and were submitted to organoleptic analysis by a panel of trained tasters. The results highlighted that soil water regimen affects some nutraceutical components and the sensory evaluation of olive oil. Cultivar also affected yield components, polyphenols, and tocopherols content, but less than soil water availability. The plants on the soil inducing a relatively more intense and longer water deficit during summer (a Skeleti Calcaric Regosol) had an early ripening and gave the best results in terms of phenolic compounds and, consequently, antioxidant properties of the olive oil. The sensorial properties of the oil obtained from both cultivars on the Regosol were superior in both years of the trial.