Although weight loss has many health benefits for people with overweight/obesity, its potential negative impact on bone health needs to be considered. This review provides a comprehensive overview of the effects of intentional weight loss achieved by lifestyle changes on bone health outcomes in adults with overweight/obesity and discusses potential mechanisms underlying the observed skeletal effects and protective measures to preserve bone health in this context. Weight loss achieved through lifestyle modifications increases surrogate markers of bone resorption and small but persistent reductions in bone mineral density at clinically relevant sites (mainly at the level of the hip). Based on limited available data, weight loss achieved by lifestyle modifications may increase fragility fractures. Combating sedentary lifestyles and promoting exercise, particularly resistance exercise, adequate intakes of calcium (diets and/or supplements), vitamin D supplementation, and higher dietary protein intakes could attenuate but not fully prevent the increased bone turnover or bone loss often associated with intentional weight loss. Further research needs to explore the skeletal effects of pragmatic interventions that match clinical scenarios, verify if changes in bone macro- and/or microstructure translate to an increased fracture risk, and investigate novel/combined strategies to improve bone health due to weight loss.