Patients with vertebral fragility fractures often experience chronic pain, postural and balance disorders, and poor quality of life (QoL). Although several studies have investigated the role of rehabilitation in severe osteoporosis, the effectiveness of this intervention in patients with multiple vertebral fractures is poorly known. The aim of our longitudinal cohort study is to evaluate the effectiveness of rehabilitation, including postural training, resistance exercises, and visual stabilization exercises, for a 7-week period, on the pain, postural balance, and QoL of subjects with at least two vertebral fragility fractures receiving denosumab and vitamin D. We investigated, before (T0) and after (T1, at 7 weeks) rehabilitation, the following outcome measures on 28 patients: pain (Numerical Rating Scale (NRS)), self-perceived QoL (36-Item Short Form Survey (SF-36) and Mini-Osteoporosis Quality of Life Questionnaire (Mini-OQOL)), dizziness (Dizziness Handicap Inventory (DHI-I)), mobility (Timed-Up and Go (TUG) test), and instrumental posturographic assessment (FreeMed posturography system). At the end of the treatment, improvements of pain and QoL were recorded. Pain relief was highly obtained in patients with more than two vertebral fractures. Moreover, a significant functional improvement (TUG test) was found in those with two vertebral fractures, without any statistically significant change reported for other outcomes. Our findings suggest that combined intervention, including anti-osteoporotic drugs and postural rehabilitation, should be proposed to osteoporotic patients with multiple vertebral fractures.