In the past decade, Internet of Things (IoT) technologies have become more and more pervasive, allowing the development of Ambient Intelligence and Context Awareness applications. While the smart home is the chosen scenario for such technologies, a variety of environments could potentially benefit from the synergies between IoT and digital applications. Among them, the clinical waiting rooms is an environment facing several challenges, particularly after the COVID-19 pandemic. Clinical waiting rooms are crowded places associated with stress and anxiety, often linked to patients’ idling time. Nonetheless, the rise of IoT-enabled telehealth has focused attention on the possibility of changing the functions of clinical waiting rooms. In this work, we conducted a systematic literature review to identify the existing solutions for “smart waiting rooms”. The review process started with 278 works, and it identified 16 papers relevant to the topic of smart clinical waiting rooms. Moreover, the results of this review underlined that waiting rooms are a neglected research area that could take advantage of IoT and Artificial Intelligence (AI) technologies to enhance patients’ experience and support the diagnostic process. Leveraging the research directions identified in the review process, this work proposes a “Smart Waiting Room” that exploits virtual reality (VR), AI, and IoT technologies to support the diagnostic process (via a cognitive assessment) and the personalization of the patient’s context—taking into account the features of the physical environment. The prototypical smart waiting room constitutes an example of the potentialities of novel technologies applied to healthcare and can contribute to shaping the future of clinical waiting rooms.