Ok so in Oct, we are going down to WDW. My family is flying in from ME. and my sister is flying in from WY. Now because of us arriving at different times we decided to use DME to get to All Star Music. The next day we pack up and move to an off site condo for the next 2 weeks, still going to WDW just staying off property. My question is, can I ride DME back to the airport where I will rent a van for the rest of my 2 weeks. By using DME the first day I am saving big time over renting that one extra day.
If I'm interpreting what you said correctly, you're staying at All-Star Music for one night. Your entire family will take DME to Music, and then the next morning (which will be your check-out morning at Music) you would take DME *back* to the airport to rent the van you need for the rest of your trip. After picking up the van, you'd drive BACK to Music to pick up your family and luggage to drive to your off-property accommodations.
Yes, you will be able to do that, because you'd be taking DME on both your check-in and check-out days. (Though you might have to call the DME office directly to set up the return without associating it with a flight, rather than Disney reservations)
*But* what might be easier would be to rent from one of the on-property rental locations. National and Alamo both have desks on Disney property: at the Car Care Center near the MK parking lot, and at the Dolphin. The CCC location (and perhaps the Dolphin, too) will send out a van to pick you up at your hotel and bring you to the office.
If those aren't the companies you prefer, I know a few of the other major rental companies have desks at hotels along Hotel Plaza Blvd near Downtown Disney. They're a short walk from the Marketplace. (When searching for locations on their sites, specifically look for "Hotel Plaza Blvd, Lake Buena Vista" as their address)
And you don't need to worry about extra charges when renting in one location and dropping off in another (i.e. renting on-property and then returning it at the airport when you leave). It's Florida law that rental car companies cannot charge a drop fee as long as pickup and return are both within Florida.
-Rob