The use of remote sensing techniques to extract vegetation cover information for the assessment and monitoring of land degradation in arid environments has gained increased interest in recent years. However, such a task can be challenging, especially for medium-spatial resolution satellite sensors, due to soil background effects and the distribution and structure of perennial desert vegetation. In this study, we utilised Pleiades high-spatial resolution, multispectral (2m) and panchromatic (0.5m) imagery and focused on mapping small shrubs and low-lying trees using three classification techniques: 1) vegetation indices (VI) threshold analysis, 2) pre-built object-oriented image analysis (OBIA), and 3) a developed vegetation shadow model (VSM). We evaluated the success of each approach using a root of the sum of the squares (RSS) metric, which incorporated field data as control and three error metrics relating to commission, omission, and percent cover. Results showed that optimum VI performers returned good vegetation cover estimates at certain thresholds, but failed to accurately map the distribution of the desert plants. Using the pre-built IMAGINE Objective OBIA approach, we improved the vegetation distribution mapping accuracy, but this came at the cost of over classification, similar to results of lowering VI thresholds. We further introduced the VSM which takes into account shadow for further refining vegetation cover classification derived from VI. The results showed significant improvements in vegetation cover and distribution accuracy compared to the other techniques. We argue that the VSM approach using high-spatial resolution imagery provides a more accurate representation of desert landscape vegetation and should be considered in assessments of desertification.