When is the best time to start shopping around for a
dvc rental? I have airfare booked for ***.
Your dates are going to be deleted because using exact dates is too close to advertising for a ressie, so I left them out of my response.
I didn't look at a calendar, but if that is Easter Week, you should be ready to book almost immediately. In order to get the resort of your choice, you will need to make arrangements with a
DVC owner who owns at that resort to get the 11-month booking window advantage.
Also, can the dining plan be added when you book a rental through a dvc owner instead of directly through disney?
Yes. Actually,
DDP can only be added through the owner you rent from. They control the reservation from the start until you check in, and only they can make arrangements like DDP and DME. You pay for DDP at checkin, not to the owner.
I'm new to this and am trying to figure out if it's better to book everyting seperate and get a "villa" or just book a package through Disney. Myself, my husband and 10 year old son will be travelling, just waiting to see if my sister in law, husband and 2 kids will be joining us.
Honestly, booking a rental including inlaws is sort of a rental scenario from Hell. If they cancel for some reason, someone is likely to lose money...probably you. In fact, many knowledgeable owners would not make that kind of reservation because of the risks involved for everyone. Most would recommend having the inlaws make their own arrangements, either by renting or direct from Disney.
You should go to the Rent/Trade board and read ALL of the "stickies" at the top of the page to get an idea of the process. Also, read this thread:
DVC Point Rental Primer
Good luck.