Information regarding tree water status in irrigated olive orchards is essential for managing growth to optimize yields and olive oil quality. One management practice option is to monitor or sample individual trees and use this information for orchard-scale management. This study assessed the ability of thermal imaging to provide the spatial distribution and variability of tree water status in a commercial irrigated olive orchard, and described strategies and a procedure for choosing which individual trees best represent the orchard. The study employed gradual upscaling from individual trees grown in lysimeters, through a controlled experimental field plot, to a commercial orchard. Thermal imaging of olive trees grown in lysimeters attested the sensitivity of the technique to identify mild-level water stress by correlating crown temperatures to stem water potential. Knowledgeable choice of five or 10 representative trees in the experimental plot, based on the histogram distribution obtained for the entire experimental orchard, lead to successful reconstruction of the spatial distribution of canopy temperature, and thus of water status. Positively skewed distributions of crown temperatures found in both the field plot and commercial orchard suggested distinct patterns, where the canopy temperature of the majority of the trees was lower than the average, and a relatively small number of trees had significantly higher temperatures and suggest commercial practicality of the proposed methodology. Thermal imaging can therefore serve as a useful tool for determining representative trees that, if frequently monitored, or instrumented with continuous water status sensors, can provide important information for orchard water management.