Our study examines the urban vegetation - air temperature (T-a) - land surface temperature (LST) nexus at micro- and regional-scales to better understand urban-climate dynamics and the uncertainty in using satellite based LST for characterizing T-a. While vegetated cooling has been repeatedly linked to reductions in urban LST, the effects of vegetation on T-a, the quantity often used to characterize urban heat islands and global warming, and on the interactions between LST and T-a are less well characterized. To address this need we quantified summer temporal and spatial variation in T-a through a network of 300 air temperature sensors in three sub-regions of greater Los Angeles, CA, which spans a coastal to desert climate gradient. Additional sensors were placed within the inland sub-region at two heights (0.1 m and 2 m) within three groundcover types: bare soil, irrigated grass, and underneath citrus canopy. For the entire study region, we acquired new imagery data, which allowed calculation of the normalized difference vegetation index (NDVI) and LST. At the microscale, daytime T-a measured along a vertical gradient, ranged from 6 to 3 degrees C cooler at 0.1 and 2 m, underneath tall canopy compared to bare ground respectively. At the regional scale NDVI and LST were negatively correlated (p < 0.001). Relationships between diel variation in T-a and daytime LST at the regional scale were progressively weaker moving away from the coast and were generally limited to evening and nighttime hours. Relationships between NDVI and T-a were stronger during nighttime hours, yet effectiveness of mid-day vegetated cooling increased substantially at the most arid region. The effectiveness of vegetated T-a cooling increased during heat waves throughout the region. Our findings suggest an important but complex role of vegetation on LST and T-a and that vegetation may provide a negative feedback to urban climate warming. (C) 2016 Elsevier B.V. All rights reserved.