Selected superior olive cultivars cultivated on a large scale in various countries in the Mediterranean region were tested in a special saline irrigation experimental plot established in 1997 in the center of the semiarid Israeli Negev area. The plot comprised two subplots containing the same 12 olive cultivars in a mirror image design. One subplot was drip-irrigated with tap water (1.2 dS·m−1) and the second with moderate saline water (4.2 dS·m−1). All cultivation practices applied to the two subplots were similar in terms of fertilization, irrigation, soil leaching, and so on. The present study summarizes the vegetative and reproductive response of the tested olive cultivar trees during the 5 years after they reached maturation and full yield. Evaluation of trunk growth, olive yield, oil percentage, olive oil yield, and fatty acid composition of the oil, sodium and chloride leaf levels, and soil fractions up to 90 cm enabled characterization and comparison of the horticultural performance of the various olive cultivars intensively cultivated with the two tested irrigation treatments. The data clearly showed a significant difference between the tested cultivars in terms of growth, yield, and oil parameters. Grouping the tested cultivars in terms of olive oil production yielded the following three groups: Group A—‘Barnea’, ‘Maalot’, and ‘Picholin’—their average oil yield ranged from 8 to 10 kg/tree; Group B—‘Souri’, ‘Frantoio’, ‘Leccino’, ‘Arbequina’, ‘Picual’, ‘Kalamata’, ‘Koroneiki’, and ‘Picholin di Morroco’—their average oil yield ranged from 5 to 8 kg/tree; and Group C—‘Picudo’—ranged from 3 to 4 kg/tree. Saline irrigation treatment at 4.2 dS·m−1 demonstrated only a low rate of retardation effect on growth or yield of olive trees compared with water at 1.2 dS·m−1 of the same cultivar in each subplot. The data obtained from the present study suggest that efficient productive cultivation of mature olive cultivars in Israeli Negev semiarid conditions, irrigated with moderate saline water, is closely related to proper soil leaching methodology and maintaining the soil electrical conductivity level in the root zone in a range lower than 6 dS·m−1.