Background and Objectives: Falls are frequent among the elderly, imply large social and economic costs, and have serious outcomes. The purpose of this study was to investigate the links between insomnia, comorbidities, multisite pain, physical activity, and fall risk in the elderly. Materials and Methods: This retrospective cross-sectional study included persons recruited from nursing homes for the elderly in Timisoara. We separated the participants into two groups by the absence (group I) or presence of fractures (group II) starting with the age of 65 years. Participants were asked how they feel about their sleep using one item on a 4-point scale from the Assessment of Quality of Life questionnaire. The risk of fall was evaluated using the Falls Risk Assessment Tool. Results: The study enrolled 140 patients with a mean age of 78.4 ± 2.4 years (range 65–98 years), 55 of them being males (39%). By comparing the two groups, we found that the elderly with a history of fractures had a greater number of comorbidities, a higher risk of fall, and more severe sleep disturbances. When using univariate logistic regression, the occurrence of fractures in the elderly was significantly associated with the number of comorbidities, the risk of fall, and the presence of sleep disturbances (p < 0.0001). The multivariate regression analysis selected four independent parameters significantly linked to fractures, and these were the number of comorbidities (p < 0.03), the risk of fall score (p < 0.006), and the sleep disturbances of type 3 (p < 0.003) and 4 (p = 0.001). Conclusions: A fall-risk score over 14 and a number of comorbidities over 2 were notably associated with the occurrence of fractures. We also found strong positive correlations between the type of sleep disturbance and the risk of fall score, the number of comorbidities, and the number of fractures in the elderly.