Background: Stroke is a serious health problem that can lead to the development of depressive symptoms, sleep disturbances, and functional dependence in stroke survivors. The change in stroke survivors’ quality of life results in negative health outcomes for stroke survivors and caregivers. This study aims to investigate the association between sleep quality and depressive symptoms among stroke survivors and caregivers in Saudi Arabia. Methods: A cross-sectional design was used to collect data from 100 stroke survivors and 80 caregivers using the patient health questionnaire and Pittsburgh Sleep Quality Index. Results: 43% of the stroke survivors reported depressive symptoms and 65% had poor sleep quality; 21% of the caregivers reported depressive symptoms and 46% reported poor sleep quality. A strong association between sleep quality and depressive symptoms was detected for the stroke survivors and caregivers: (r = 0.885, p < 0.001); (r = 0.669, p < 0.001), respectively. A strong association was found between caregivers’ depressive symptoms and patient post-stroke depressive symptoms (r = 0.502, p < 0.001). A moderate association was found between stroke survivors’ sleep quality and caregivers’ sleep quality (r = 0.407, p < 0.001). There was a moderate association between stroke survivors’ depressive symptoms and caregivers’ sleep quality (r = 0.456, p < 0.001). Moreover, there was a moderate association between stroke survivors’ sleep quality and caregivers’ depressive symptoms (r = 0.492, p < 0.001). Conclusion: Poor sleep quality and depressive symptoms are common among stroke survivors and caregivers. This study found an association between the two variables. Therefore, depressive symptoms and sleep disturbances in stroke survivors and caregivers should receive more attention. Future research should focus on an interventional study to enhance sleep quality and decrease the risk of depressive symptoms.