If you've used heat transfer vinyl you know you can't iron on slick material. A friend discovered (quite by accident but I'm SO glad she did) that if you lightly steam regular vinyl it will stay a LONG time.
So I used outdoor quality vinyl cut it out (regular cut NOT reverse) and then lightly ironed it with a little steam to "stick" it permanently. (If I hadn't used the iron it would come off the first day of use) I used the same vinyl on the plastic cups but no ironing needed :)