Children living in food-insecure households have poorer overall health than children in food-secure households. While U.S. nutrition assistance programs provide resources, these cannot consistently offer age-appropriate nutritional foods for young children. This study aimed to determine community stakeholders’ perceptions of the barriers and facilitators to obtaining adequate, high-quality, and age-appropriate foods for children ages 0–3 in Florida before and during COVID-19. Community stakeholders (n = 32) participated in a 60 min interview via Zoom using a semi-structured script based on the PRECEDE component of the PRECEDE–PROCEED model. Interviews were transcribed verbatim and coded by two researchers using a thematic analysis approach. Stakeholders’ perceptions revealed a lack of awareness surrounding eligibility for assistance programs, a lack of knowledge regarding how to obtain resources and services, and stigma associated with receiving benefits. These remained significant barriers to obtaining healthful foods for households with young children before and during COVID-19. Nonetheless, barriers were exacerbated during the pandemic. Unemployment rates rose, intensifying these households’ financial hardships and food insecurity levels. Likewise, stakeholders suggested the need for families to become more aware of federal assistance eligibility requirements and available opportunities via social media and referrals. Identifying risk factors associated with food insecurity can inform future interventions to safeguard young children’s health and well-being.