Irrigation of olive orchards is challenged to optimize both yields and oil quality. Best management practices for olive irrigation will likely depend on the ability to maintain mild to moderate levels of water stress during at least some parts of the growing season. We examined a number of soil, plant and remote sensing parameters for evaluating water stress in bearing olive (var. Barnea) trees in Israel. The trees were irrigated with five water application treatments (30, 50, 75, 100 and 125% of potential evapotranspiration) and the measurements of soil water content and potential, mid-day stem water potential, and stomatal resistance were taken. Remote thermal images of individual trees were used to alternatively measure average canopy temperature and to calculate the tree's crop water stress index (CWSI), testing empirical and analytical approaches. A strong non-linear response showing similar trends and behavior was evident in soil and plant water status measurements as well as in the CWSI, with decreasing rates of change at the higher irrigation application levels. No statistically significant difference was found between the analytical and the empirical CWSI, suggesting that the relative simplicity of the analytical method would make it preferable in practical applications.