The endocannabinoid system is a neurobiological signaling network that is present in the human biological systems, including the brain. This neurobiological system comprises cannabinoid receptors, endogenous ligands, as well as enzymatic synthesis, degradation and transport of endocannabinoids and has been suggested as a modulator of multiple physiological processes, including the sleep–wake cycle. On the other hand, the COVID-19 pandemic, originated by the novel coronavirus SARS-CoV-2, has caused global catastrophes in economic, social, and health spheres. COVID-19 is a multi-organ disease with a broad spectrum of health complications, such as respiratory infections leading to respiratory-related symptoms and disorders. The development, approval, and application of vaccines against SARS-CoV-2 is ongoing; however, there are increasing reports of prolonged effects after COVID-19 infection, including respiratory and neurological sequelae. Here, I provide a comprehensive review of the current literature on the endocannabinoid system and their role in sleep modulation. Whilst I discuss relevant considerations for the high risk for developing sleep disorders related to respiratory failures, such as obstructive sleep apnea (OSA) in recovered COVID-19-infected subjects. Finally, I propose a framework that integrates the analysis of the components of the endocannabinoid system as prognostic biomarkers of the likely OSA after COVID-19 infection.