Add 2 cups or 16-ounces of whipping cream in a stand mixer or in a large bowl. Using the stand or hand mixer, whip the cream for about 3 - 5 minutes on medium speed or until it forms soft peaks.
Add the 14-ounce can of sweetened condensed milk and ½ teaspoon vanilla. Whip to combine.
Add in 16-ounces of crushed pineapple that has been drained and stir.
Pour the pineapple ice cream into a freezer-safe loaf pan or dish. Cover and freeze the ice cream for 8 hours or until completely frozen.
