Sending luggage to resort via DME?
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I would say yes. You would at least have to be scheduled to take the DME, but I don't know if it's based upon that or if it's based upon when you check in at DME. You could call them and ask. The number is 1-866-599-0951. I'll be interested to hear what you find out.
DME works the same way airlines do. Your luggage does not travel unless you do. In other words, if you want Disney to transport your luggage, you need to be on the bus. If you are not, don't expect your luggage to show up at the resort.