Direct answer
Rolandi's for classic Italian-leaning Playa pizza. La Famiglia for thin-crust wood-fired. Pizza Pazza for Neapolitan. Don Sirloin (not really pizza but their pizza-by-the-slice late-night is legendary). Skip 5th Ave chains — better pizza one street over.
Playa has a real Italian expat community, so the pizza scene is better than you'd expect. Rolandi's is the long-running benchmark. La Famiglia (Calle 38) does proper thin-crust wood-fired. Pizza Pazza leans Neapolitan. For late-night, Don Sirloin's pizza-by-the-slice on 5th and Calle 28 is a Playa institution.
