Discriminating between woody plant species using a single image is not straightforward due to similarity in their spectral signatures, and limitations in the spatial resolution of many sensors. Seasonal changes in vegetation indices can potentially improve vegetation mapping; however, for mapping at the individual species level, very high spatial resolution is needed. In this study we examined the ability of the Israel/French satellite of VENμS and other sensors with higher spatial resolutions, for identifying woody Mediterranean species, based on the seasonal patterns of vegetation indices (VIs). For the study area, we chose a site with natural and highly heterogeneous vegetation in the Judean Mountains (Israel), which well represents the Mediterranean maquis vegetation of the region. We used three sensors from which the indices were derived: a consumer-grade ground-based camera (weekly images at VIS-NIR; six VIs; 547 individual plants), UAV imagery (11 images, five bands, seven VIs) resampled to 14, 30, 125, and 500 cm to simulate the spatial resolutions available from some satellites, and VENμS Level 1 product (with a nominal spatial resolution of 5.3 m at nadir; seven VIs; 1551 individual plants). The various sensors described seasonal changes in the species’ VIs at different levels of success. Strong correlations between the near-surface sensors for a given VI and species mostly persisted for all spatial resolutions ≤125 cm. The UAV ExG index presented high correlations with the ground camera data in most species (pixel size ≤125 cm; 9 of 12 species with R ≥ 0.85; p < 0.001), and high classification accuracies (pixel size ≤30 cm; 8 species with >70%), demonstrating the possibility for detailed species mapping from space. The seasonal dynamics of the species obtained from VENμS demonstrated the dominant role of ephemeral herbaceous vegetation on the signal recorded by the sensor. The low variance between the species as observed from VENμS may be explained by its coarse spatial resolution (effective ground spatial resolution of 7.5) and its non-nadir viewing angle (29.7°) over the study area. However, considering the challenging characteristics of the research site, it may be that using a VENμS type sensor (with a spatial resolution of ~1 m) from a nadir point of view and in more homogeneous and dense areas would allow for detailed mapping of Mediterranean species based on their seasonality.