Water availability for agricultural use is currently a global problem that worsens with climate change in several regions of the world. Among grain legumes, common bean (Phaseolus vulgaris) is the most cultivated in the worldwide. The Chilean germplasm of common bean is characterized by tolerance to water stress. Here, we analyzed a selection of nine ancient Chilean landraces in regard to their drought tolerance, simulating optimal (OW) and restricted watering (RW) in a Mediterranean environment. Phenological, growth, and yield traits were recorded, and correlation analysis was performed. Accordingly, leaf temperature and osmotic potential were higher under RW, while the leaf chlorophyll content decreased in all landraces. Physiological maturity days and seed-filling days were lower in RW than in OW. This similarly occurred with the grain yield. The % yield reduction was negatively correlated with the % pod reduction and the relative rate of leaf expansion (RLAE) reduction. However, the 100-seed weight value was not significantly modified by water treatment (p > 0.05). For instance, landraces that preferred to fill the grain with a lower rate of leaf expansion showed a lower loss in grain yield under drought conditions. These results suggest that the resource partitioning between growing leaves, flowers, and developing pods in Chilean landraces is variable, affecting the common bean drought tolerance.