Hydrogen peroxide (H2O2) is a crucial reactive oxygen species (ROS) involved in regulating both physiological and pathological processes. Excessive H2O2 production can lead to oxidative stress, contributing to aging, cancer, and neurodegenerative diseases. In contrast to other ROS exhibiting short lifespans, H2O2 is relatively stable, and its spatial and temporal dynamics are central to understanding its pathophysiological role. Therefore, the development of fluorescent probes that are highly selective, sensitive, and capable of a rapid response is still required. To date, numerous fluorescent probes have been developed. Among them, boronic acid triggers have attracted considerable attention but often suffer from limited reactivity, preventing real-time H2O2 monitoring. To overcome this lack of reactivity, we report the design and synthesis of new borinic acid-based fluorogenic probes for H2O2 detection in cellular environments. These probes are based on a hemicyanine scaffold functionalized with the borinic acid trigger, which demonstrated superior kinetics compared to its boronic counterpart. These probes enable efficient real-time monitoring of H2O2 in cellular models, both extracellularly and intracellularly. The kinetics of these enzyme-free chemical probes matched that of the gold standard Amplex UltraRed/horseradish peroxidase (HRP) assay, representing a significant advancement in the field and offering a versatile and sensitive tool for studying H2O2-mediated cell signaling.