Swaziland has one of the highest HIV/AIDS prevalences in the world, which has contributed to many Swazi children being left as “orphans and vulnerable children” (OVC). In 2010, there were 78,000 AIDS orphans in the country and the number is expected to increase given the current HIV prevalence. The WHO aims to close the gap in a generation and eliminate health inequality; as a result the Swazi Government began in 2005 to provide financial support to the education of OVC. Prior research has indicated that household characteristics are some of the major determinants with respect to schooling status among children. We have examined the association between household characteristics and schooling status of OVC. Schooling status may vary by gender and by age, as well as by other sociodemographic factors, in sub-Saharan African societies, and therefore we have also included a comprehensive set of appropriate variables in all of our multivariate analyses. Using existing data from the Swaziland Multiple Indicator Cluster Survey 2010, a total of 5890 children aged 7–18 years old were analyzed. The results from the multivariate logistic regressions showed that non-OVC were more likely than OVC to be in school (OR = 2.18, p < 0.001), even after taking other variables into considerations. The OVC in socioeconomically disadvantaged households, such as those with lower levels of household wealt, and those who resided in an urban area, were less likely to be in school. These findings suggest that education programs for OVC need to be household-appropriate.