Low vitamin D levels among older people represent a significant health problem worldwide. This study aimed to examine the factors associated with vitamin D deficiency in older people (aged ≥ 65) in the Kuwaiti population. A cross-sectional study was conducted in seven primary healthcare centers across Kuwait (November 2020 to June 2021). The participants (n = 237) had their serum vitamin D (25(OH)D) concentrations (analyzed using LC-MS) classified as sufficiency 75 nmol/L (30 ng/mL) or deficiency < 75 nmol/L (below 30 ng/mL). The data were collected using self-administered questionnaires and face-to-face interviews with participants in geriatric clinics. Binomial logistic regression analysis was applied to assess factors associated with vitamin D deficiency. Vitamin D deficiency was found to be present in two thirds of the participants (n = 150, 63%), with a higher prevalence of deficiency in participants who did not receive vitamin D supplements, compared to those who did (84% vs. 16%, p = 0.001). The results from the binary logistic regression showed that a low duration of sun exposure (OR = 0.24, 95% C.I. [0.08−0.7], p = 0.011), dark skin pigmentation (OR = 4.46, 95% [1.35−20.49], p = 0.026), and lower caloric intake (OR = 0.9, 95% C.I. [0.85−0.96], p = 0.001) were risk factors for vitamin D deficiency. Furthermore, a significant inverse relationship was found between vitamin D levels and parathyroid hormone (PTH) levels (OR = 1.16, 95% C.I. [1.04−1.31], p = 0.016). These findings support the recommendation that vitamin D supplementation and adequate sunlight exposure are necessary for raising low vitamin D levels in older people in Kuwait.