Climate change models predict an increase in aridity, especially in the regions under Mediterranean-type climates such as the Mediterranean Basin. However, there is a lack of ecophysiological studies supporting the selection of the more drought-adapted ecotypes for reforestation programs. In this study, we analyzed the anatomical and functional adaptations of 18-month-old seedlings to drought on 16 Quercus suber L. populations from the southeastern rear edge of the species distribution in northern Tunisia growing in a common garden, in order to identify the most appropriate material to use in reforestations. The results evidenced that populations from more xeric habitats displayed the highest leaf dry mass per area (LMA) and lowest leaf area (LA) values, together with the largest increase in the bulk modulus of elasticity (Δε) in response to drought (i.e., elastic adjustment). On the other hand, some populations with intermediate values of aridity, LMA and LA displayed the sharpest increase in proline concentration (ΔPro), with a concomitant increase in osmotic potential at full turgor (Δπo) (i.e., osmotic adjustment). Therefore, two different strategies seem to drive the within-species variation of the studied Q. suber populations in response to water scarcity: (i) a water saver strategy for improving water stress tolerance through the maximization of the elastic adjustment; and (ii) a water spender strategy for maintaining water absorption and photosynthetic activity under moderate water stress through the maximization of the osmotic adjustment. We concluded that the higher elastic adjustment, together with reduced LA and increased LMA, implied a better performance under drought stress in the populations of Q. suber from more xeric habitats, which can be considered the most drought-adapted ecotypes and, consequently, the most appropriate for reforestation programs under an eventual increase in aridity.