(1) Background: This study investigated the relationship between weather conditions, diurnal patterns, and total knee range of motion (ROM), as well as the severity of symptoms (pain and stiffness) in older adults with knee osteoarthritis. (2) Methods: An exploratory longitudinal study was conducted on 28 older adults with knee osteoarthritis (mean age 71.86 ± 4.49 years; 46.4% men, 53.6% women). We used as assessment tools the Visual Analog Scales (VAS) for self-reported local knee pain and stiffness, and goniometry for ROM. Measurements were taken twice, six months apart, in winter and summer, in the morning and evening of each selected day. Recorded weather factors comprised temperature, relative humidity, barometric pressure, and maximum wind speed. (3) Results: The study revealed significant effects of season and time of day on pain and stiffness, respectively (p < 0.001). Additionally, a significant interaction between season and time influenced total knee ROM (p < 0.001). Moreover, there was a statistically significant relationship between time and total knee ROM (p < 0.001). (4) Conclusions: This research underscores the complex link between seasonal fluctuations and daily variations in some symptomatic and functional aspects of knee osteoarthritis in older adults.