Island ecosystems have distinct and unique vulnerabilities that place them at risk from threats to their ecology and socioeconomics. Spatially exhibiting the fragmentation process of island landscapes and identifying their driving factors are the fundamental prerequisites for the maintenance of island ecosystems and the rational utilization of islands. Haitan Island was chosen as a case study for understanding landscape fragmentation on urbanizing Islands. Based on remote sensing technology, three Landsat images from 2000 to 2020, landscape pattern index, transect gradient analysis, and moving window method were used in this study. The results showed that from 2000 to 2020, impervious land increased by 462.57%. In 2000, the predominant landscape was cropland (46.34%), which shifted to impervious land (35.20%) and forest (32.90%) in 2020. Combining the moving window method and Semivariogram, 1050 m was considered to be the best scale to reflect the landscape fragmentation of Haitan Island. Under this scale, it was found that the landscape fragmentation of Haitan Island generally increased with time and had obvious spatial heterogeneity. We set up sampling bands along the coastline and found that the degree of landscape fragmentation, advancing from the coast inland, was decreasing. Transects analysis showed the fragmentation intensity of the coastal zone: the north-western and southern wooded zones decreased, while the concentration of urban farmland in the north-central and southern areas increased. The implementation of a comprehensive experimental area plan on Haitan Island has disturbed the landscape considerably. In 2000, landscape fragmentation was mainly influenced by topography and agricultural production. The critical infrastructure construction, reclamation and development of landscape resources have greatly contributed to the urbanisation and tourism of Haitan Island, and landscape fragmentation in 2013 was at its highest. Due to China’s “Grain for Green Project” and the Comprehensive Territorial Spatial Planning policy (especially the protection of ecological control lines), the fragmentation of Haitan Island was slowing. This study investigated the optimal spatial scale for analyzing spatiotemporal changes in landscape fragmentation on Haitan Island from 2000 to 2020, and the essential influencing factors in urban islands from the perspective of natural environment and social development, which could provide a basis for land use management and ecological planning on the island.