While play-based learning is important for a high quality early education, only when teachers are confident and competent in enacting play-based learning in their everyday practice are expected benefits of play-based learning for whole-child development realized. A sample of 592 early childhood educators who assumed different job titles in Hong Kong kindergartens participated in this study. This study investigated the roles of these educators' perceptions of personal and organizational enabling factors in facilitating teachers' enactment of play-based learning and further their perceived children's whole-child development. Research Findings: These educators reported that two personal enablers (i.e. beliefs of play-based learning and self-efficacy beliefs) and two organizational enablers (i.e. teacher collaboration and home-kindergarten collaboration) were positively associated with their enactment and further enhanced their perceived whole-child development through different mechanisms. Teachers' reported enactment of play-based learning played significant mediation roles. Practice or Policy: Policy makers and change facilitators should convey clear messages and take effective measures to promote play-based learning in kindergartens. Kindergarten principals need to create a mutually supportive climate in the kindergarten to praise and appreciate teachers' good practice of play-based learning, and enhance two kinds of collaborative relationships: teacher collaboration and home-kindergarten collaboration.