Physalia physalis, often referred to colloquially as Portuguese man-of-war or bluebottle jellyfish, is a jellyfish-like organism found in tropical and subtropical areas of the Pacific, Atlantic, and Indian Oceans. Most often, envenomation by P. physalis tentacles results in painful but self-resolving epidermal stings. We report on two clinic visits of a patient who suffered from worsening reactions to recurrent P. physalis envenomation. The first clinical episode involved urticaria and severe pruritus that was worse than the pruritus the patient had experienced upon envenomation in the past. The second episode involved an unusual bullous reaction. Further study into the compounds present in P. physalis venom may help elucidate the mechanism of the present case and other abnormal reactions to envenomation. Patients and providers who care for patients at risk for recurrent stings (e.g., surfers, fishermen) should be cognizant of the potential for worsening reactions to envenomation. Further study into therapies such as oral antihistamines and Aloe vera gel may uncover additional appropriate treatments for symptomatic relief of P. physalis envenomation.