Pinus halepensis Mill. is a conifer typical of Mediterranean pinewoods adapted to drought and fire. Although the timing of seasonal events in P. halepensis is strongly associated with these stressors and other environmental factors, needle phenology and litter flammability are insufficiently characterized at the intraspecific level. These traits can be informative of the existence of locally adapted populations across the species’ distribution range, and remote sensing approaches are promising tools to infer phenological changes in forest trees. In this study, we investigated intraspecific differentiation of P. halepensis related to needle phenology at the onset of the fire season (May-June) through vegetation indexes (VIs) obtained from unmanned aerial vehicles. We collected drone images using multispectral and RGB sensors for 56 adult populations of P. halepensis categorized into five ecotypes growing in two common gardens located in Spain under contrasting conditions (dry-continental versus wet-coastal). In the dry trial, we additionally monitored the temporal variation of RGB-derived indexes using two flights spaced over a one-month period. We also performed four consecutive ground measurements of needle pigments and fuel moisture content and obtained litter flammability traits for a subset of populations. Most in situ measurements and flammability traits did not show population differentiation. Regarding RGB-derived VIs, we did not detect obvious temporal patterns which differed among populations. However, we observed greener canopies in June than in May, which are indicative of the pace of current-year needle development. We also deduced an earlier phenology (i.e., earlier current-year needle unfolding) in the dry-continental trial. Ecotypic differentiation was found for some vegetation indexes related to needle unfolding (i.e., TCARI/OSAVI) and old needle senescence (i.e., PRSI). These differences were generally consistent across trials and time, and fundamentally indicated that sub-humid ecotypes typical of the eastern Mediterranean showed earlier needle unfolding and old needle senescence than semiarid ecotypes thriving in western continental Mediterranean areas. The intraspecific divergence observed in early season phenology is potentially related to the existence of contrasting life-history strategies present at the intraspecific level for the species. In particular, some semi-arid ecotypes, which are known to optimize the trade-off between carbon gain and water loss, exhibited an early old needle senescence (high likelihood of crown fire development) coupled with a late needle unfolding (conservative water use). These results indicate a possible trade-off between drought and fire resistance for the species, which suggest the importance of considering the intraspecific characteristics of Aleppo pine in forest management actions.