Utilization of remote sensing-derived meteorological data is a valuable alternative for tropical insular territories such as Puerto Rico (PR). The study of ecosystem resilience in insular territories is an underdeveloped area of investigation. Little research has focused on studying how an ecosystem in PR responds to and recovers from unique meteorological events (e.g., hurricanes). This work aims to investigate how an ecosystem in Western Puerto Rico responds to extreme climate events and fluctuations, with a specific focus on evaluating its innate resilience. The Antillean islands in the Caribbean and Atlantic are vulnerable to intense weather phenomena, such as hurricanes. Due to the distinct tropical conditions inherent to this region, and the ongoing urban development of coastal areas, their ecosystems are constantly affected. Key indicators, including gross primary production (GPP), normalized difference vegetation index (NDVI), actual evapotranspiration (ET), and land surface temperature (LST), are examined to comprehend the interplay between these factors within the context of the Culebrinas River Watershed (CRW) ecosystem over the past decade during the peak of hurricane season. Data processing and analyses were performed on datasets provided by Moderate Resolution Imaging Spectroradiometer (MODIS) and Landsat 8–9 OLI TRIS, supplemented by information sourced from Puerto Rico Water and Energy Balance (PRWEB)—a dataset derived from Geostationary Operational Environmental Satellite (GOES) data. The findings revealed a complex interrelationship among atmospheric events and anthropogenic activities within the CRW, a region prone to recurrent atmospheric disruptions. NDVI and ET values from 2015 to 2019 showed the ecosystem’s capacity to recover after a prolonged drought period (2015) and Hurricanes Irma and Maria (2017). In 2015, the NDVI average was 0.79; after Hurricanes Irma and Maria in 2017, the NDVI dropped to 0.6, while in 2019, it had already increased to 0.8. Similarly, average ET values went from 3.2339 kg/m2/day in 2017 to 2.6513 kg/m2/day in 2018. Meanwhile, by 2019, the average ET was estimated to be 3.8105 kg/m2/day. Data geoprocessing of LST, NDVI, GPP, and ET, coupled with correlation analyses, revealed positive correlations among ET, NDVI, and GPP. Our results showed that areas with little anthropogenic impact displayed a more rapid and resilient restoration of the ecosystem. The spatial distribution of vegetation and impervious surfaces further highlights that areas closer to mountains have shown higher resilience while urban coastal areas have faced greater challenges in recovering from atmospheric events, thus showing the importance of preserving native vegetation, particularly mangroves, for long-term ecosystem stability. This study contributes to a deeper understanding of the dynamic interactions within urban coastal ecosystems in insular territories, emphasizing their resilience in the context of both natural atmospheric events and human activity. The insights gained from this research offer valuable guidance for managing and safeguarding ecosystems in similar regions characterized by their susceptibility to extreme weather phenomena.