Appropriate warming of the periocular or posterior cervical skin has been reported to induce autonomic or mental relaxation in humans. To clarify the effects of cutaneous warming on human sleep, eight male subjects with mild sleep difficulties were asked to try three experimental conditions at home, each lasting for 5 days, in a cross-over manner: warming of the periocular skin with a warming device for 10 min before habitual bedtime, warming of the posterior cervical skin with a warming device for 30 min before habitual bedtime, and no treatment as a control. The warming device had a heat- and steam-generating sheet that allowed warming of the skin to 40 °C through a chemical reaction with iron. Electroencephalograms (EEGs) were recorded during nocturnal sleep using an ambulatory EEG device and subjected to spectral analysis. All the participants reported their sleep status using a visual analog scale. We found that warming of the periocular or posterior cervical skin significantly improved subjective sleep status relative to the control. The EEG delta power density in the first 90 min of the sleep episode was significantly increased under both warming of the periocular or posterior cervical skin relative to the control. These results suggest that warming of appropriate skin regions may have favorable effects on subjective and objective sleep quality.