For species of conservation concern, long-term monitoring is vital to properly characterize changes in population distribution and abundance over time. In addition, long-term monitoring guides management decisions by informing and evaluating the efficacy of management actions. A long-term monitoring initiative for the federally threatened Stephens' Kangaroo rat (Dipodomys stephensi, SKR) was established in 2005, across 628 hectares within Marine Corps Base Camp Pendleton (MCBCP), San Diego, California, USA. From 2005 to 2018, we tracked trends in area occupied by SKR, trends in relative SKR densities within occupied habitat, and modeled probabilities of SKR occupancy, colonization, extinction, with habitat, climate, and disturbance covariates. Area occupied by SKR increased almost 2-fold from 2005 to 2018 on MCBCP, while density in occupied habitat increased almost 3-fold. Increased area occupied was correlated with increases in estimated density among years, indicating SKR population growth occurs by expansion into suitable habitat patches, as well as increases in numbers within occupied habitat. SKR occupancy was positively associated with gentle slopes (<10%) and moderate open ground (40–80%) and forb cover (>40%). They were more likely to colonize previously unoccupied habitat when there were moderate levels of open ground (40–80%) and low shrub cover (<20%), while more likely to go locally extinct in areas with high slopes (>10%), less open ground (<20%), and increased non-native grass cover (>40%). Additionally, probabilities of SKR occupancy and colonization were higher in areas with moderate levels of disturbance, which was positively associated with open ground and forb cover. We conclude that long-term occupancy and density monitoring is effective in informing status and trends of spatially dynamic species and that moderate habitat-based disturbance is compatible with the management of SKR.