To make sugar-free syrup: Combine the powdered monk fruit sweetener and water in a small skillet. Stir to combine and heat until the sweetener dissolves completely, approximately 3-4 minutes. Remove from heat and set aside to cool.
Place the frozen pineapple, pineapple juice, coconut cream, rum, and one-quarter cup of simple syrup into a blender and blend until smooth.
While the blender is still running, add the ice a little at a time until the desired consistency is reached.
Turn the blender off and remove the lid. Taste and add additional simple syrup, if desired, and blend for another 30 seconds to combine.
To serve, pour into glasses and serve immediately garnished with fresh pineapple slices.
Notes
You can use fresh, frozen, or canned pineapple for this recipe but for best results, use fresh pineapple that has been cut into chunks and frozen prior to blending.