Dockless bike sharing plays an important role in residents’ daily travel, traffic congestion, and air pollution. Recently, urban greenness has been proven to be associated with bike sharing usage around metro stations using a global model. However, their spatial associations and bike sharing usage on public holidays have seldom been explored in previous studies. In this study, urban greenness was obtained objectively using eye-level greenness with street-view images by deep learning segmentation and overhead view greenness from the normalized difference vegetation index (NDVI). Geographically weighted regression (GWR) was applied to fill the research gap by exploring the spatially varying association between dockless bike sharing usage on weekdays, weekends, and holidays, and urban greenness indicators as well as other built environment factors. The results showed that eye-level greenness was positively associated with bike sharing usage on weekdays, weekends, and holidays. Overhead-view greenness was found to be negatively related to bike usage on weekends and holidays, and insignificant on weekdays. Therefore, to promote bike sharing usage and build a cycling-friendly environment, the study suggests that the relevant urban planner should pay more attention to eye-level greenness exposure along secondary roads rather than the NDVI. Most importantly, planning implications varying across the study area during different days were proposed based on GWR results. For example, the improvement of eye-level greenness might effectively promote bike usage in northeastern and southern Futian districts and western Nanshan on weekdays. It also helps promote bike usage in Futian and Luohu districts on weekends, and in southern Futian and southeastern Nanshan districts on holidays.