Rinse cranberries and remove any that are soft or bruised.
Place the 12 ounces cranberries into a food processor or blender; pulse until cranberries are finely chopped but not pureed.
Place crushed cranberries in a bowl and sprinkle 1/2 cup of sugar and 1 tablespoon orange zest over the cranberries and toss to coat. Cover with plastic wrap and place in refrigerator for at least 1 hour.
In a separate bowl, beat the softened 4 ounces cream cheese and remaining 1/2 cup of sugar, together until smooth and fluffy.
Gradually add the 1 cup heavy cream and 1 teaspoon vanilla extract to the cream cheese mixture. Continue to beat until the mixture is combined and forms stiff peaks.
In a large bowl, combine the cranberry mixture, drained 8 ounces crushed pineapple and the cream cheese mixture. Fold together until well incorporated. Then gently fold in the 2 cups mini marshmallows.
Cover the bowl with plastic wrap and refrigerate for 1 hour.
Best serve chilled with cookies, pretzels, and fruit.