Little is known about COVID-19 vaccine hesitancy and acceptance among individuals experiencing homelessness, despite their higher risk for morbidity and mortality from SARS-CoV-2. This study examines COVID-19 vaccination attitudes and uptake among U.S. military Veterans experiencing homelessness enrolled in transitional housing programs funded by the U.S. Department of Veterans Affairs (VA). Telephone interviews were conducted with 20 Veterans in California, Florida, Iowa, Kentucky, and Massachusetts, USA (January–April 2021). A rapid analysis approach was used to identify and enumerate commonly occurring themes. Although 60% of interviewed Veterans either received the COVID-19 vaccine or were willing to do so, one-third expressed hesitancy to get vaccinated. COVID-19 vaccination attitudes (e.g., belief that the vaccines were inadequately tested), military experience, beliefs about influenza and other vaccines, and sources of information emerged as influential factors for COVID-19 vaccination uptake or hesitancy. Veterans in VA-funded homeless transitional housing programs are generally willing to be vaccinated. However, a substantial minority is reluctant to take the vaccine due to concerns about the COVID-19 vaccine and distrust of authority. Recommendations for increasing uptake include utilizing Veteran peers, homeless service providers, and healthcare providers as trusted messengers to improve confidence in the vaccine.