@Kris-Dykema - my first question would be whether this is an integrated listing? I'm guessing it's not since you are directly making changes to both your HomeAway calendar and your MyVR calendar?
Which calendar is your MASTER calendar? It's imperative that you choose one calendar and make that your master. Then your changes should ONLY happen there. Other calendars may import to your master, and your master may export to the other calendars. But if you manually manipulate several, you'll have never ending confusion. I recommend MyVR as your master calendar.
That said, if your listings are not integrated, you'll need to set up an import to MyVR from any listings that will generate bookings, and an export to all listings from your MyVR calendar.