Wash the strawberries and pat them completely dry.
Cut off the stem end of each strawberry to create a flat base. Then cut off the pointed tip of each strawberry and set the tips aside to use as the Santa hats.
Pat the cut surfaces dry so the cream cheese filling stays in place.
In a large mixing bowl, beat together the softened cream cheese, powdered sugar, and vanilla extract until smooth and creamy.
Transfer the cream cheese mixture to a piping bag fitted with a large round tip.
Pipe the cream cheese mixture onto the larger strawberry pieces to create the Santa faces.
Gently place the reserved strawberry tips on top to form the hats.
Using a small piping tip, pipe a small amount of the cream cheese mixture onto the tip of each hat to create a pom-pom and onto the front of each strawberry to create a button.
Gently press mini chocolate chips into the cream cheese filling to create the eyes.