Mix together the box of jello and boiling water in a large bowl. Stir until all jello is dissolved. Mix in can of pineapple and can of pie filling until combined. Pour jello mixture into a 9x13 pan and refrigerate until set (about 4-5 hours).
Mix together cream cheese, sour cream, sugar, and vanilla and beat until smooth. Place a spoonful of cream on each serving. Garnish with fresh berries.