I travel with frozen meat on all my trips there, anything from steaks, shrimp, alligator and bison. I vac pack and freeze solid. Pack your cooler tight with a few frozen gel packs and place the whole cooler in the freezer until you walk out the door for the airport. I have done this where I get to the hotel, line the trash can with a clean plastic bag, put your meat in there and get ice from the machine...keep adding ice as it melts. Even better yet is if your cooler is not too large and you can put it in the can and cover it with ice. One time I purchased a styrofoam cooler at Riteway (14.00...ouch) and did this until I was able to get into the villa the next day. Where I was staying was limited on freezer space. Repack in the am and repeat at the next place.

It is a long time but may be doable with a lot of effort. I mainly do this because we want specific cuts or things. If you are doing this just for chicken / pork chops etc Riteway has a nice selection of meat and the prices are not too crazy so buying there may be easier.
Lunch meat and cheeses are also fairly reasonable in price....I would not bring those down again like we have the first few trips.

I think vacuum sealing helps greatly as things are air / water /leak proof and seem to stay frozen longer and also keep longer when thawed. You will have to be flexible in your menu and eat things in the order that they thaw.