Land cover analysis is a key method used to understand past land use patterns and explore the driving forces and processes behind them. This study focuses on land cover in 18 counties and cities of Hainan Island, delving into the driving factors of land cover in specific areas of Hainan Island, including the southern, northern, eastern, western, inland, and coastal regions. The effects of socio-economic factors, landscape pattern, and urban functional units on land cover are considered, and three hypotheses are proposed to explain the observed trends. The results indicate that house prices are positively correlated with construction area, woodlands land, and urban green space, thereby supporting the luxury effect hypothesis on land cover. In addition, construction age was negatively correlated with the woodlands area, confirming the role of the inverse legacy effect hypothesis in land cover. Other relationships between urban functional units and land cover emphasized the importance of the land use hypothesis in land cover planning. These results will help decision-makers and managers to better understand the current drivers of land cover, allowing for a more scientific basis when planning and managing urban land cover.