OP, my approach seems very much like yours. This summer we rented a fun house an hour away in a big city (we live in a very rural area.) The house was a huge, funk-ily decorated Victorian with a pool. We spent the whole week getting good, international take out, playing board games, and watching movies. Not the usual family vacation, but it was a nice get away. We were set to do the same over Christmas, but had really hoped to have a couple of the college kids' roommates come too. That got canceled as everyone would have had to go home for Christmas and THEN to our vacation. Too much germ mixing for me at that point.
So, I vote for Key West, or some other area where you can rent a house/condo, get takeout or eat outdoors, and that requires a minimum of points of contact with lots of the public during travel.
As an aside, to fellow readers, I'd like to add that the vaccine currently has not been proven to prevent contraction or spread of the virus. The studies were designed only to determine if it kept the vaccinated individual from getting sick. I'm confident further studies are in the process to determine transmissibility, but until then, we have to act like we're contagious even if vaccinated.
Also, a negative test to get on a plane or enter a country is only as good as the number of people that person has encountered a few days prior and several days after the test. If you are too early into your infection, you will test negative. If you get exposed while walking out of the testing center, it's moot. A good study came out from New Zealand (where they have great control over entry and tracking) about a man who was negative right before the flight, came down with symptoms while in quarantine, and ultimately had infected several people on the plane.
And, finally, going to WDW, eating in restaurants, etc, and not getting sick in no way implies you were never infected or contagious. Studies indicate that at least 50% of transmission seems to occur in asymptomatic people just going about their business. My hospital has mandatory testing before routine surgeries and 5-10% of my patients test positive despite have no symptoms.
OP, I'm betting you know all this already, and I'm not singling anyone out. I'm just presenting facts so that everyone has them. I'm a physician and just want to make sure everyone knows the complete range of consequences for their decisions based on the science we currently have.