We travel to Hilton Head and Florida for extended stays via car at least twice a year from here in Baltimore. Our packing list includes:
Kitchen: KitchenAid containers (trying hard to have different lids than the ones there), Cutco knives, a good small frying pan, cutting board, olive oil, spices, and some dry goods (cereal, mac and cheese), pizza pan, and whatever is in our fridge (milk, fruit, eggs) in a cold bag; might bring some wine down
Office: portable desk (maybe not needed as most resorts have one we've discovered), 24" monitor, speakers, web cam, power strips (one for regular plugs and one for USB power chargers)
Living/Exercise: My road bike, fluid bike trainer, small fan, Roku, yoga mats, small dumbbells, small suitcase for overnight stops, tablet for workout videos, sometimes golf clubs
We have some of that stuff permanently in a box, the rest we just grab the night before. We get all of that plus our clothes, etc. into a Mazda CX-5 (with a bike rack) without much trouble, though it's like a jigsaw puzzle making it fit and be able to keep driver vision in the mirrors.
For flying, I'm going to assume I'm not working and we'll take most of the "Kitchen" section and not the rest.