Background: Problems affecting the vaginal tract in diabetic women are very often neglected. The efficacy and safety of three gynecological treatments in diabetic women have been assessed. Materials and Methods: A single-blind randomized progressive trial on 48 diabetic women affected by vaginal dryness, dyspareunia, and recurrent Candida infections was carried out. The ICIQ Vaginal Symptoms (ICIQ-VS) questionnaire was administered. Results: The analysis of the parameters of ICIQ-VS questionnaire among the three groups showed significant difference only for “dragging pain” (p = 0.019) and “soreness” (p = 0.028). In all groups and for all parameters of the questionnaire, improvement of symptoms was observed. In particular, in Group 1 for all symptoms a highly significant difference was observed, to support the already known benefits of the products and of the proposed combination. Significant improvement was also observed in Group 2. Conclusions: The proposed treatment with DermoXENR Ultracalming Special for diabetics and DermoXEN R Vitexyl vaginal gel exert effective moisturizing and soothing action. Indeed, the aforementioned products have been proven effective for the main gynecological problems of diabetic women.