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Olive fruit maturation depends directly on the moment of olive harvest. In addition, the composition of extra virgin olive oil changes depending on the ripening degree of the fruit harvested. Likewise, using different olive cultivars in the extraction, the olive oil obtained has different quality and composition. Superintensive crops own special characteristics such as more trees per hectare than traditional crops. This improves the production of olives by surface; being superintensive more profitable than the traditional cultivar. Three different olive cultivars: Arbequina, Koroneiki, and Arbosana, and from superintensive crops with different irrigation management are used for the extraction. Olive oils are extracted at the laboratory with the Abencor system. Monounsaturated fatty acid (MUFA) content is increased by increasing the maturity index. The highest content of phenolic compounds is obtained from rainfed Koroneiki, with approximately 1 g kg−1. The maximum quantity of total lipoxygenase pathway volatile compounds is 28 mg kg−1, obtained in irrigated Arbequina olives. According to the results obtained, the optimum time of harvest is with a maturity index of approximately 2, when the content of oil, phenols, and MUFA reach their maximum. In addition, higher contents of minor components are obtained for rainfed than irrigated crops. Practical Applications: Determining the optimal stage for harvest the fruit of the olive tree is the main practical application or potential use. Additionally, to predict, approximately, the composition of an olive oil that may have according to some agronomic factors, such as the cultivar used, irrigation management, or the stage of maturation of the olive fruit. Different ripening degrees of the olive fruit, with different irrigation management and with different cultivar of olive trees, from superintensive crops are used to produce an extra virgin olive oil.