Place the fresh cranberries in a food processor and pulse until they are finely and evenly chopped, being careful not to over-process them into a mushy consistency.
Transfer the chopped cranberries to a large bowl and stir in the granulated sugar. Cover and refrigerate for at least 4 hours, or ideally overnight, to allow the sugar to macerate the berries and soften their tartness.
Place the crushed pineapple in a fine-mesh sieve and use the back of a spoon to press out all excess liquid until the pineapple is as dry as possible.
In a separate chilled bowl, beat the heavy whipping cream and alcohol-free vanilla extract until stiff peaks form.
Remove the cranberry mixture from the refrigerator and fold in the drained pineapple, mini marshmallows, toasted pecans, and orange zest until well distributed.
Using a rubber spatula, gently fold the whipped cream into the cranberry base using a slow over-under motion to maintain the light, fluffy texture.
Cover the bowl and chill in the refrigerator for at least 2 hours before serving to allow the marshmallows to soften and the flavors to fully meld.