Background <p>Medical students suffer above-average rates of depression, anxiety, stress, poor sleep, and life dissatisfaction, which impacts their performance. In addition to the demands of medical study, medical students in the Gaza Strip face coping with life in an area marred by chronic conflict and poverty.</p> Methods <p>This cross-sectional study assessed medical students at the two medical schools in the Gaza Strip. Students were randomized according to university, sex, and academic level. Screening employed the DASS21, PSQI, and SWLS instruments. Ordinal logistic regression was used to investigate predictors of anxiety, stress, depression, sleep quality, and SWLS stage. Potential predictors of poor sleep quality were assessed by binary logistic regression, and multivariable logistic regression was implemented to determine the effect of covariates.</p> Results <p>Three hundred sixty-two medical students participated. Different stages of depression, anxiety, and stress symptoms were prevalent in 69%, 77.3%, and 65.2% of students, respectively. Poor sleep quality was prevalent in 77.9% of students, and 46.1% of medical students were dissatisfied with their lives. Low income was associated with higher rates of extremely severe anxiety and with higher rates of moderate depression. Poor sleep quality was associated with higher rates of all-stage anxiety, stress, and depression in univariate regression and with higher odds of moderate anxiety and mild, moderate, and extremely severe depression in multivariable regression.</p> Conclusions <p>Medical students in the Gaza Strip suffer from high rates of depression and anxiety symptoms, stress, poor sleep, and life dissatisfaction compared to several other countries and the pooled global prevalence. Medical schools in Gaza should put forward strategies to limit the psychological burdens perceived by their students.</p>