(1) Background: Teledermatology (TD) has exponentially grown since the onset of COVID-19, as the Face-to-Face Dermatology (F-F/D) modality changed within Public Health Systems. Although studies have been conducted on health results, we did not find any that analyzed the experiences of individuals who received care through TD. Therefore, the main objective of the study was to analyze the experiences of dermatology patients and the communication with health personnel. (2) Methods: A multicenter, controlled, randomized, non-blinded clinical trial was designed. Data were collected during the six months of follow-up. Four-hundred and fifty patients participated in the present study, who were assigned to two different groups: TD and F-F/D. The sociodemographic and clinical characteristics of the participants were collected. The ‘Generic Short Patient Experiences Questionnaire’ (GS-PEQ) was used to assess patients’ experiences, and the Healthcare Communication Questionnaire (HCCQ) was used to measure the communication of patients with healthcare professionals. (3) Results: After six months of follow-up, 450 patients completed the study (TD = 225; F-F/D = 225) of which 53.3% were women, with an average age of 52.16 (SD = 19.97). The main reasons for the consultations were skin lesions (51.56%) located on the head and neck (46.8%), followed by the legs (20.7%). According to the GS-PEQ, TD users indicated having a greater confidence in the professional skills of the doctors (p < 0.01). However, the F-F/D group indicated having received more adequate information about their diagnosis/afflictions (p < 0.01), were more involved in the decisions related to their treatment (p < 0.01), and more satisfied with the help and treatment received (p < 0.01). Regarding the HCCQ, the TD group obtained better assessments with respect to if the patients had been treated in a rude and hasty manner, if the health professionals had addressed them with a smile, and if these could adequately manage the reason for the consultation (p < 0.01). (4) Conclusions: The results of the study generally showed positive experiences and communication. The TD group indicated having received less information about the diagnosis, were less involved in the decisions, and were less satisfied with the help and treatment received. However, they indicated having more confidence on the professional skills of the doctors, and that the work at the institution was better organized. In addition, they perceived better communication skills of the health professionals, although less respect for their privacy.