Understanding the spatial dynamics of invasive alien plants is a growing concern for many scientists and land managers hoping to effectively tackle invasions or mitigate their impacts. Consequently, there is an urgent need for the development of efficient tools for large scale mapping of invasive plant populations and the monitoring of colonization fronts. Remote sensing using very high resolution satellite and Unmanned Aerial Vehicle (UAV) imagery is increasingly considered for such purposes. Here, we assessed the potential of several single- and multi-date indices derived from satellite and UAV imagery (i.e., UAV-generated Canopy Height Models—CHMs; and Bi-Temporal Band Ratios—BTBRs) for the detection and mapping of the highly problematic Asian knotweeds (Fallopia japonica; Fallopia × bohemica) in two different landscapes (i.e., open vs. highly heterogeneous areas). The idea was to develop a simple classification procedure using the Random Forest classifier in eCognition, usable in various contexts and requiring little training to be used by non-experts. We also rationalized errors of omission by applying simple “buffer” boundaries around knotweed predictions to know if heterogeneity across multi-date images could lead to unfairly harsh accuracy assessment and, therefore, ill-advised decisions. Although our “crisp” satellite results were rather average, our UAV classifications achieved high detection accuracies. Multi-date spectral indices and CHMs consistently improved classification results of both datasets. To the best of our knowledge, it was the first time that UAV-generated CHMs were used to map invasive plants and their use substantially facilitated knotweed detection in heterogeneous vegetation contexts. Additionally, the “buffer” boundary results showed detection rates often exceeding 90–95% for both satellite and UAV images, suggesting that classical accuracy assessments were overly conservative. Considering these results, it seems that knotweed can be satisfactorily mapped and monitored via remote sensing with moderate time and money investment but that the choice of the most appropriate method will depend on the landscape context and the spatial scale of the invaded area.