The performance of various types of Green Stormwater Infrastructure (GSI) to improve the quantity and quality of urban-induced stormwater runoff has been extensively studied. However, the integrated benefits of GSI for runoff quantity and quality control and Urban Heat Island (UHI) reduction have been less studied. There are currently no established GSI monitoring plans in urban Southeast Florida. Therefore, this study presents, for the first time, the design of a monitoring plan to deduce the long-term performance of various GSIs across distinct urban development types in Miami, FL. The first site (Arena) consists of an infiltration trench (IT) and a rain garden on the main campus of Florida International University. The second site (Factory Town) contains a rain garden and a bioswale on a 6.5-acre post-industrial redevelopment site. The third site, within a 33-acre commercial area (Miami Design District), will provide detailed UHI signatures. The monitoring design of Arena and Factory Town sites includes spatially arranged sensors that measure continuous rainfall, soil moisture, and water levels. Continuous discharge from the 0.3-acre IT drainage area in Arena site is considered. Event-based physicochemical stormwater runoff indicators (pH, conductivity, and nutrients) are also studied at each GSI. The effect of GSI on UHI is determined by measuring continuous air temperature, relative humidity, and wind direction at both GSI and unshaded impervious locations at all sites. Results from this study determine the best continuous and event-based sampling configuration and lead to building a comprehensive database to evaluate the performance of GSIs in terms of climate resilience, urban development, and UHI.