Background/Objective Although the association of disturbed sleep with specific chronic conditions is well known, the relationship between sleep disturbances and multiple diseases is less clear. Therefore, the objectives of this study were to examine the independent relationships of various sleep disturbances with 1) multimorbidity (≥2 chronic conditions) and 2) commonly co-occurring pairs of chronic conditions. Methods Analyses were based on data from 4127 individuals aged ≥65 years participating in the population-based cross-sectional Cooperative Health Research in the Region of Augsburg (KORA) Age Study conducted from 2008 to 2009 in Germany. Sex-specific odds ratios (OR) and 95% confidence intervals (CI) were calculated from sequential logistic regression models. Results Neither short nor long daily sleep duration was significantly associated with multimorbidity among men; a significant positive relationship was identified regarding short sleep duration among women (OR 2.16, 95% CI: 1.42–3.30). While insomnia and all unique symptoms of insomnia were connected to multimorbidity among women in the multivariable models, the relationship concerning trouble falling asleep no longer remained significant after adjustment for all covariables among men. Regarding commonly co-occurring pairs of conditions, the clearest associations were observed between insomnia and daytime tiredness with joint diseases/eye diseases in men and joint diseases/heart diseases in women. Conclusions There seems to be sex-specific particularities in the relationship between sleep disturbances and sleep duration with multimorbidity and commonly co-occurring pairs of chronic conditions in older adults from the general population.