Drought is a recurring natural phenomenon with significant socio-economic and environmental impacts across South Africa. This research investigates the livelihood impacts of drought on households and organizations in the Western Cape Province of South Africa, utilizing a secondary dataset collected by the Human Sciences Research Council of South Africa. Descriptive statistics were used to describe and explore the dataset. Likewise, heterogeneous choice modeling was applied to investigate the factors influencing the levels of livelihoods impacts of drought among household and organizations. The findings underscored households’ greater vulnerability to drought compared to organizations across all the levels of drought impacts. Many households reported considerable and major impacts, which were largely due to differentials in adaptive capacity. While awareness of the drought was widespread, perception varied regarding the government’s effectiveness in managing the crisis, as less than half of the population of organizations (43.7%) and households (42.1%) have strong belief that the government was very effective in the management of drought disaster, while 30.9% and 34.6% of the organizations and households respectively, believed that the government was not effective enough with the management of drought crisis. Hygiene, chores, and gardening suffered the most among households, whereas disruption of business and financial burdens were predominant for organizations. Factors that significantly influenced the levels of drought impacts include age, institutional engagement of water restrictions, livelihood areas impacted by drought, and perceptions on water consumption rate. The study recommends heightened awareness of water conservation, compliance with restrictions, investment in infrastructure, and embracing community-based adaptation and disaster risk reduction initiatives. For organizations, emergency response plans, business continuity planning, and stakeholder engagement will be helpful to bolster resilience to drought.