Purpose: To evaluate the effects of sporting activities, training loads, and athletes’ characteristics on sleep among high-level adolescent athletes, in a controlled training and academic environment. Methods: A total of 128 high-level adolescent athletes (age = 15.2 [2.0] y), across 9 different sports, completed common sleep questionnaires and were monitored daily (7.3 [2.7] d) during a typical in-season training period. Sleep was analyzed using actigraphy and sleep diaries, whereas training load was evaluated using the session rating of perceived exertion, and muscle soreness and general fatigue were reported with the aid of visual analog scales. Separate linear mixed-effects models were fitted, including the athlete as a random effect and the following variables as fixed effects: the sport practiced (categorical predictor), daily training load, age, and sex. Different models were used to compare sleep variables among sports and to assess the influence of training load, age, and sex. Results: The mean total sleep time was 7.1 (0.7) hours. Swimmers presented increased sleep fragmentation, training loads, perceived muscle soreness, and general fatigue compared with athletes who engaged in other sports. Independent of any sport-specific effects, a higher daily training load induced an earlier bedtime and reduced total sleep time and perceived sleep quality, with higher sleep fragmentation. Moreover, female athletes experienced increased total sleep time and worse sleep quality in response to stress compared with those in males. Conclusion: In a controlled training and academic environment, high-level adolescent athletes did not achieve the recommended sleep duration. Impaired sleep quality and quantity could be partially explained by increased training loads.