Add the cranberries and granulated sugar to the bowl of a food processor and pulse until they are very well chopped, but not completely pureed. Set aside.
In a large bowl, beat the cream cheese until smooth. Add in the cold heavy cream, powdered sugar, and vanilla; whip until stiff peaks form.
If the cranberry-sugar mixture ends up being very watery, just drain it a bit. Fold in the chopped cranberries and crushed pineapple; mix well until combined.
Fold in mini marshmallows.
Cover and refrigerate for a few hours or overnight.
If it's loose, give it a gentle stir. Serve and enjoy!