Drain the pineapple; set aside. Discard the juice or save it to use in another recipe.
In a medium saucepan, combine the cranberries, sugar, and orange juice. Bring to a boil, stirring occasionally, over medium-high heat.
Reduce the heat to a low boil. Cook for 10 minutes, stirring occasionally, until the cranberries have burst and the mixture has thickened slightly. Note: The sauce will continue to thicken as it cools, so you do not need to cook it until it is very thick.
Remove from the heat. If you would like a less chunky sauce, mash the cranberries with a potato masher to the desired consistency.
Add the drained crushed pineapple and vanilla extract; stir to combine.
Transfer the cranberry sauce to a bowl. Cover and allow to cool completely at room temperature, then refrigerate until ready to serve.