The article focuses on the machining of polymeric materials polypropylene (PP) and un-plasticized poly vinyl chloride (PVC-U) after surface treatment with polyurethane and acrylate coatings using waterjet technology. Two types of waterjet technologies, abrasive waterjet (AWJ) and waterjet without abrasive (WJ), were used. The kerf width and its taper angle, at the inlet and outlet of the waterjet from the workpiece, were evaluated. Significant differences between AWJ and WJ technology were found. WJ technology proved to be less effective due to the creation of a nonuniform cutting gap and significant burrs. AWJ technology was shown to be more efficient, i.e., more uniform cuts were achieved compared to WJ technology, especially at a cutting head traverse speed of 50 mm·min−1. The most uniform kerf width or taper angle was achieved for PP + MOBIHEL (0.09°). The materials (PP and PVC-U) with the POLURAN coating had higher values of the taper angle of the cutting gap than the material with the MOBIHEL coating at all cutting head traverse speeds. The SEM results showed that the inappropriate cutting head traverse speed and the associated WJ technology resulted in significant destruction of the material to be cut on the underside of the cut. Delamination of the POLURAN and MOBIHEL coatings from the base material PP and PVC-U was not demonstrated by SEM analysis over the range of cutting head traverse speeds, i.e., 50 to 1000 mm·min−1.