Advances in estimating actual evapotranspiration (ETa) with remote sensing (RS) have contributed to improving hydrological, agricultural, and climatological studies. In this study, we evaluated the applicability of Vegetation-Index (VI) -based ETa (ET-VI) for mapping and monitoring drought in arid agricultural systems in a region where a lack of ground data hampers ETa work. To map ETa (2000–2019), ET-VIs were translated and localized using Landsat-derived 3- and 2-band Enhanced Vegetation Indices (EVI and EVI2) over croplands in the Zayandehrud River Basin (ZRB) in Iran. Since EVI and EVI2 were optimized for the MODerate Imaging Spectroradiometer (MODIS), using these VIs with Landsat sensors required a cross-sensor transformation to allow for their use in the ET-VI algorithm. The before- and after- impact of applying these empirical translation methods on the ETa estimations was examined. We also compared the effect of cropping patterns’ interannual change on the annual ETa rate using the maximum Normalized Difference Vegetation Index (NDVI) time series. The performance of the different ET-VIs products was then evaluated. Our results show that ETa estimates agreed well with each other and are all suitable to monitor ETa in the ZRB. Compared to ETc values, ETa estimations from MODIS-based continuity corrected Landsat-EVI (EVI2) (EVIMccL and EVI2MccL) performed slightly better across croplands than those of Landsat-EVI (EVI2) without transformation. The analysis of harvested areas and ET-VIs anomalies revealed a decline in the extent of cultivated areas and a loss of corresponding water resources downstream. The findings show the importance of continuity correction across sensors when using empirical algorithms designed and optimized for specific sensors. Our comprehensive ETa estimation of agricultural water use at 30 m spatial resolution provides an inexpensive monitoring tool for cropping areas and their water consumption.