They are going to ship it within a few days of when you order it, so order it about 8-10 days before you're going to arrive. I've heard lots of people say they ship packages to themselves (snacks, diapers, etc.) and I am confident that Pop will hold it for you. I'm thinking of ordering a case of water from Staples myself.
See if you can somehow work your confirmation # into the address, and the "Hold for Guest" bit, too. You'll have to look up the resort's street address.
One tip about tracfone, you can activate the phone without adding the minutes card. It will give you starter minutes. It's 20 when you do it on the web, but I'm not sure--it might only be 10 when you do it on the phone. Anyway, it also comes with 60 days airtime. If you add your phone card separately later (even if it's 10 minutes later), you'll get an additional 90 days airtime in addition to the added minutes. And FatWallet.com has a great thread with bonus codes for additional minutes when redeeming an airtime card.
I've used my tracfone when over the border in Canada, but I wasn't far over the line. You might still be able to use it when you get home.