Olive groves in the Mediterranean may lose production sustainability because of their vulnerability to climatic change. Irrigation is an important measure that could significantly affect fruit yield, olive fruit fly infestation, and oil characteristics. The aim of paper was to compare the regulated deficit irrigation with different water management practices, in consecutive years, in two locations in Zadar County (Croatia), affecting fruit morphology, olive fruit fly infestation, and quantity and quality of the extracted Coratina cultivar oil. Treatments, namely C—rainfed, T1—deficit irrigation (produce’s practice), T2—regulated deficit irrigation, and T3—full irrigation (100% ECTO), were established. Irrigated treatments had a positive effect on all morphological characteristics of the fruit. The pulp mass, independently of the year, increased in irrigated treatment (ranging from 1.04 to 1.65 in C to 2.25 and 2.30 in the irrigated treatments) and resulted in a higher oil content on a fresh weight basis (ranging from 16.39% to 17.85% in C to 19.48% to 23.26% in the irrigated treatments). However, fruit yield per tree was only location-dependent. When olive fruit fly presence was high, fruit infestation was greatest in the irrigated compared to the rainfed treatment. According to quality parameters, all oils were classified as EVOO. Individual phenols were influenced by irrigation, while the composition of fatty acids was more influenced by location than treatment. The sensory characteristics of the resulting oil were slightly reduced compared to rainfed treatment. The results indicate that regulated deficit irrigation benefits water use sustainability without compromising the quality of the oil.