The aim of this study was to investigate whether the nighttime cortisol release was associated with subjective and objective sleep quality and the discrepancy between them. Forty-five healthy older adults (age range from 56 to 75 years) collected salivary samples immediately before sleep and immediately after awakening on two consecutive nights. Actigraphy was used to assess objective sleep quality and quantity. A sleep diary was used to assess subjective sleep quality. Linear mixed models were performed using subjective and objective sleep quality data from 76 nights to investigate between-subject associations. We observed that larger changes in cortisol levels between sleep onset and awakening, reflecting a healthier circadian rhythm of the Hypothalamic-Pituitary-Adrenal (HPA) axis, were associated with better subjective sleep quality, but not with objective sleep quality. Moreover, smaller changes in nighttime cortisol were associated with lower subjective sleep quality relative to objective sleep quality. All these results were observed even after controlling for important confounders such as sleep quantity, age, sex, subjective socioeconomic status, stress perception, depression, physical activity, and adherence to the salivary sampling protocol. This study demonstrates that subjective sleep quality in older people may be explained, to some extent, by the activity of the HPA axis.