I voted yes b/c we've done it in the past but it was a PITA. I guess it's b/c our carry ons don't have wheels (they hook onto the handle of our big wheeled bags) and our kids were too little to really help out. It was a pain to lug all thru the airport and at the gate. Also it was before the liquids ban.
I can fit all 4 of our clothes into 1 large wheeled suitcase (checked.) Toiltetries in a carry on size which we also check cuz I like full size bottles. We check a 2nd carryon with misc. stuff. Collapsible cooler, swim goggles for kids, microwave popcorn, trial size laundry detergent, etc.
We have a TS condo with a washer/dryer. I pack 2-3 outfits per person (shirt, shorts, socks, undies) and 1-2 nightgowns/pj's pp. If there's a good chance of it being chilly (Oct-March) I pack 1 pr long pants pp.
Approx every other day when we get back from the parks, I toss in a load before we head to the pool. Toss in dryer when we go to sleep. Fold and put away in am while I have my morning coffee. I'm usually the 1st one up so this works well.
I don't wear make up. I bring 1 bottle of sunblock and a travel size of moisturizer. We all share 1 shampoo but bring kids their toothpaste. I try to estimate 1 weeks worth and as our trip gets closer, put aside that bottle so I can toss it out at the end of our trip. Dh and boys share a brush and I have 2 (1 flat, 1 round) I'm not a big hair stylin' type. I shower/blow dry every morning but it's always a bad hair day in FL, sweaty and usually just put in a pony tail by midafternoon. Esp. after a few times on SpM. Dh and I both hate to shave (2x each for the week max) so we share 1 razor and 1 travel size shave gel. We toss this before we leave too.
I'm not "into" shoes. I just bring a good pair of running sneakers (need good support, even on hottest days), flip flops for the pool and that's it. I usually wear the sneakers on the plane to lighten the bag but on our recent trip out west I wore the flip flops for easy on/off going thru security and liked it.
I don't bring robes, slippers, towels (why on Earth would you bring all this crap from home??!!) Esp. towels!! They are supplied there.
All we carry on the plane now is a backpack with 2 port. dvd players, 2 PSP's, 2 Nintendo DS's, and dh's iPod. 4 ear-bud type headphones. Also all paperwork.
We check 1 large, 2 small bags. We could probably get by with 1 large, 1 small but then the big bag would go overweight, esp. when cruising cuz then there's beach shoes, snorkel gear, etc. (For cruising we bring 2 big bags, 2 small and 2 garment bags though we didn't use a lot of it. I ended up doing laundry on the ship cuz it was right across the hall from our cabin and I couldn't stand it piling up in that tiny room.)
If I run into a situation that I need something, I stop at the Walgreen's on our way to the parks. no biggie. It's not like we're moving to Mars.
), shoes, lots of sunscreen, etc). I said clothes aren't my problem, but if I'm traveling in hot weather I do like to change clothes twice a day. We usually go back to the room after lunch, take a bath and get cooled off. I then hate to put dirty clothes back on. I am also a very light sleeper that can't sleep without noise, so always carry a white noise machine. I have to have that thing. My clothes would stay home before the white noise machine would.
If the screeners are giving others a hard time I will divide my baggies between 2 bins. They have better things to do than count ziplocks! 
