Emerging piezoelectric technologies have promoted the development of self‐powered sensing systems by addressing the power supply issue of wearable electronics, offering fascinating prospects in Internet of Things. Despite tremendous progress in stretchability, there remain a lot of urgent and unmet needs for stretchable self‐powered piezoelectric sensors toward real‐world applications: (i) lack of practicability due to the low sensitivity in the stretching mode; (ii) self‐healing ability after mechanical damage to enhance device sustainability and durability; (iii) requirements of biocompatibility as electronics attach to human body. In this review, the trends, challenges, and solutions in elastomer‐based stretchable self‐powered piezoelectric sensors, focusing on their material design and fabricating strategy for high sensitivity, self‐healing ability, and biocompatibility is introduced. The structure‐property relationships of these novel strategies and their emerging applications is discussed and highlighted. Finally, the current challenges and perspectives for the development of stretchable self‐powered piezoelectric sensors are presented.