In a mixing bowl beat the cream cheese until smooth. Add in half of the condensed milk, vanilla, and about 1/4 cup of the pineapple and mix well.
In another mixing bowl, beat the heavy cream and the rest of the condensed milk together until it thickens enough to form soft peaks.
Fold the thick cream mixture in with the cream cheese mixture until blended.
Pour half of the mixture into a loaf pan (or another freezer-safe dish). Then add the crushed pineapple over it.
Pour the rest of the mixture over the pineapple.
Using a knife, spoon or fork make a few swirl motions through the mixture.
Place in freezer for 6-8 hours to freeze.