Vegetation seasonality is a critical indicator of ecological responses to global climate change, especially in the Iberian Peninsula, where the intersection of human activity and climate variability amplifies these effects. Understanding these changes is vital for adopting ecogeographical sustainability and developing effective climate adaptation strategies. This study examines trends in vegetation seasonality in the Iberian Peninsula from 1982 to 2023, based on weekly AVHRR NDVI data (2184 images). By integrating Seasonal Trend Analysis (STA) with Robust Trend Analysis (RTA)—including the Theil–Sen (TS) slope estimator, the Contextual Mann–Kendall (CMK) test (α = 0.05), and false discovery rate (FDR) control—we identified significant phenological shifts and widespread vegetation greening. The results reveal a regional response to global patterns of climate change, with 94.2% of the study area exhibiting significant trends, particularly in the Mediterranean ecoregion, where earlier growing seasons are becoming increasingly common. These shifts highlight the urgent need for sustainable land and resource management in the face of accelerating global change. Our findings provide critical insights into the ecological dynamics of the Iberian Peninsula, offering a robust foundation for formulating policies that promote environmental sustainability and enhance resilience to climate change.