Hydrocarbon-contaminated soils are considered as one of the major environmental issues that harm human well-being, particularly in arid regions of the world. Phytoremediation is a possible mitigation measure for this issue and has been suggested as it is cost-effective compared with other remediation technologies for soil clean-up, such as soil thermal treatment and soil washing. However, there are still gaps in the literature regarding the behavior of annual and perennial desert plants and their ability to survive in hydrocarbon-contaminated soils in arid ecosystems. Therefore, this study aims to develop an integrated approach using remote sensing techniques to understand the behavior of annual and perennial desert plants over different types of oil-contaminated soils (oil tarcrete, wet-oil lake, bare soil, and vegetation cover) in the Kuwait Desert and to explore the impact of climate and physical soil properties on the regrowth of native desert plants. The Normalized Difference Vegetation Index (NDVI), Normalized Difference Water Index (NDWI), and ferrous iron (Fe2+) index (FI) were used to determine the changes in oil contamination and vegetation cover from 1992 to 2002, and 2013–2020. Subsequently, statistical tests were performed to determine the influence of climatic and soil physical characteristics on changes in hydrocarbon contamination and desert plant behavior. The results showed that hydrocarbon contamination was high at the study sites in the first six years (1992–1997) after contamination, and then decreased in the following years. However, vegetation cover was low in the first six years but significantly increased after 1998, reaching >65%. It was also found that annual plants had the highest distribution rate compared to perennial plants, which mainly depended on the soil type. We concluded that certain annual and perennial plants could successfully grow over tarcrete-contaminated sites, making these sites more suitable for the restoration of native desert plants than hydrocarbon-contaminated sites. We also observed that the succession process of vegetation growth over hydrocarbon-contaminated soils could be associated with vegetation growth on a clean sediment layer covering the oil layer. Additionally, we observed that the remobilization of aeolian sediment over many contaminated sites in Kuwait resulted in the accumulation of organic matter, plant seeds, and dust particles that create layers of nutrient-rich soil for the initial growth of plants.