Data assimilation techniques allow researchers to optimally merge remote sensing observations in ecohydrological models, guiding them for improving land surface fluxes predictions. Presently, freely available remote sensing products, such as those of Sentinel 1 radar, Landsat 8 sensors, and Sentinel 2 sensors, allow the monitoring of land surface variables (e.g., radar backscatter for soil moisture and the normalized difference vegetation index (NDVI) and for leaf area index (LAI)) at unprecedentedly high spatial and time resolutions, appropriate for heterogeneous ecosystems, typical of semiarid ecosystems characterized by contrasting vegetation components (grass and trees) competing for water use. A multiscale assimilation approach that assimilates radar backscatter and grass and tree NDVI in a coupled vegetation dynamic–land surface model is proposed. It is based on the ensemble Kalman filter (EnKF), and it is not limited to assimilating remote sensing data for model predictions, but it uses assimilated data for dynamically updating key model parameters (the ENKFdc approach), including saturated hydraulic conductivity and grass and tree maintenance respiration coefficients, which are highly sensitive parameters of soil–water balance and biomass budget models, respectively. The proposed EnKFdc assimilation approach facilitated good predictions of soil moisture, grass, and tree LAI in a heterogeneous ecosystem in Sardinia for a 3-year period with contrasting hydrometeorological (dry vs. wet) conditions. Contrary to the EnKF-based approach, the proposed EnKFdc approach performed well for the full range of hydrometeorological conditions and parameters, even assuming extremely biased model conditions with very high or low parameter values compared with the calibrated (“true”) values. The EnKFdc approach is crucial for soil moisture and LAI predictions in winter and spring, key seasons for water resources management in Mediterranean water-limited ecosystems. The use of ENKFdc also enabled us to predict evapotranspiration and carbon flux well, with errors of less than 4% and 15%, respectively; such results were obtained even with extremely biased initial model conditions.