Dice 1 pound of pineapple spears and set aside.
Place remaining pineapple, coconut milk, coconut cream, condensed milk, lime juice and zest, and rum (if using) into the well of a blender and blend until mixture is smooth.
Spoon a couple tablespoons of the diced pineapple into each Italian Ice pop sleeve, and using a funnel fill the sleeves with the blended pina colada mixture, leaving about a ½ inch space at the top. Seal. Lay each sleeve onto a baking sheet, in a single layer and place into the freezer. Freeze ice pops for at least 5 hours. Serve.