Background/Objectives: Studies have shown a high prevalence of anemia and vitamin D insufficiency in older adults, and the literature suggests a relationship between these two conditions, as vitamin D insufficiency may impair erythrocyte synthesis. Food insecurity refers to the lack of regular access to sufficient and nutritious food, which can directly affect health by worsening conditions such as anemia and vitamin D insufficiency. This study evaluated the association between vitamin D insufficiency and anemia in older adults. Methods: We conducted a cross-sectional study with 430 individuals aged 60 and older, using personal interviews and blood tests for data collection. Anemia was identified with serum hemoglobin levels of <12 g/dL for women and <13 g/dL for men, while vitamin D insufficiency was defined as serum levels <30 ng/mL. We used multiple logistic regression to analyze associations through Stata version 17.0 software. Results: The prevalence of anemia was identified in 14.7% of the sample, and vitamin D insufficiency was observed in 63.5%. We found an association between vitamin D insufficiency and anemia (OR = 2.4; 95% CI = 1.2–4.7). In the final model, factors such as male sex (OR = 2.7; 95% CI = 1.5–4.9) and polypharmacy use (OR = 2.0; 95% CI = 1.0–3.9) were also associated, regardless of age group, food insecurity, and multimorbidity. Conclusions: Vitamin D insufficiency increased the likelihood of anemia among the older adults evaluated, suggesting that prevention and treatment strategies for anemia should consider vitamin D serum levels.