In a blender, pour in the cans of crushed pineapple (pineapple and their juice), the sugar, juices of both the lemon and lime, and the vanilla. Blend for about 2 minutes or until completely smooth.

Cut the frozen Cool Whip in quarters and place it in the blender. Blend on high until combined and smooth. Mixture will be thick but still pourable.

Pour the mixture into two Mason jars with the lids off. Place the Mason jars into the freezer and freeze for about 3 hours, or until the mixture is soft and thick, like soft serve. Serve immediately. I find that in my freezer, 3 hours is the perfect amount of time for thick and creamy soft serve-style Dole Whips, but check yours after 2 and experiment with times from the 2-hour mark.