Regenerative agricultural practices are a suitable path to feed the global population. Integrated Crop–livestock systems (ICLSs) are key approaches once the area provides animal and crop production resources. In Brazil, the expectation is to increase the area of ICLS fields by 5 million hectares in the next five years. However, few methods have been tested regarding spatial and temporal scales to map and monitor ICLS fields, and none of these methods use SAR data. Therefore, in this work, we explored the potential of three machine and deep learning algorithms (random forest, long short-term memory, and transformer) to perform early-season (with three-time windows) mapping of ICLS fields. To explore the scalability of the proposed methods, we tested them in two regions with different latitudes, cloud cover rates, field sizes, landscapes, and crop types. Finally, the potential of SAR (Sentinel-1) and optical (Sentinel-2) data was tested. As a result, we found that all proposed algorithms and sensors could correctly map both study sites. For Study Site 1(SS1), we obtained an overall accuracy of 98% using the random forest classifier. For Study Site 2, we obtained an overall accuracy of 99% using the long short-term memory net and the random forest. Further, the early-season experiments were successful for both study sites (with an accuracy higher than 90% for all time windows), and no significant difference in accuracy was found among them. Thus, this study found that it is possible to map ICLSs in the early-season and in different latitudes by using diverse algorithms and sensors.