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I think the medium one would suffice. Make sure you surround it in enough padding!

Dimensions of the medium boxes (pulled from USPS's website):

Priority Mail Medium Flat Rate Box (FRB1) $10.95 11" x 8-1/2" x 5-1/2"
Priority Mail Medium Flat Rate Box (FRB2) $10.95 13-5/8" x 11-7/8" x 3-3/8"
 
I shipped mine in a medium box and with a bunch of newspaper as padding. The iPad was in it's original box as well inside the USPS box.
 
How about the one that it fits in.

Post office only has one large box shape, two medium shapes, a small box, and some envelopes all at the same price.

I sold my iPad on eBay, and now need to buy a shipping label on paypal. What size flat rate box will it take to fit the iPad comfortably?
 
Use the flat rate medium box. I would stuff it with both peanuts and wrap the actual iPad with a ton of bubble wrap, unless you have the box. Both are available at Walmart for about $5. Don't forget to insure it though!
 

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I sold mine last week and went with the large and it was too big. The medium should work best.
 
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