I could use some tips from folks who travel with only a carryon. I am a horrible over-packer, so I can’t wrap my mind around it.
I might be able to swing another Disney trip soon if I can find a way to cure my checked bag addiction. 
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So far 5 days is my limit. We did a WDW trip 2 Aprils ago for 5 days (or maybe even 5 nights? I can’t remember) and we did carry on only. My biggest issue with longer trips is actually needing to bring full sized hair products for my precious curls.
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Season matters, of course. But generally, you have to think about minimums. What is the minimum number of shirts you will need, then add one for good measure. Pants or shorts? Wear one pair on the plane, and then pack one additional. If it is particularly hot, maybe two or three additional…but you can get away with re-wearing bottoms. Consider packing laundry sheets (that is, it is laundry soap, but in what looks like small laundry sheets, which can use, in a pinch, to wash your clothes in a sink if you don’t want to use the resort laundry).
For shirts, if the weather allows it, consider layers. Only the layers closest to the skin really need to be changed when it is cooler. Of course, when it is hotter temps, that’s not going to work because you’ll sweat through both!!!
Don’t forget to take advantage of your personal item. Pack as much as you can in the carry-on, but make sure you take full advantage of the maximum space that your personal item allows to pack additional clothes.
Save space by relying on in-room amenities as much as possible. I know the water in Florida does horrible things to your hair…but maybe relying on a hat or just living with untidy hair (it is vacation) is just something to deal with for a week!
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Are you in a 1-BR villa with washer / dryer, or are you ok with using a resort laundry facility?
Personally, I can travel with 7 days in a carry-on. My wife has more trouble, mostly because of toiletries (many of which are larger than 3 oz, and some that she can fit in a 3oz container would run out).
For me the limit is how many days of clothes I can fit in a bag if there’s no in-room laundry. If there is in-room laundry, I could travel indefinitely with a carry-on, as long as I could buy gel and toothpaste if I ran out.
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LOL I have a feeling @TheSafetyLady will have a different perspective on this point than you. 
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Well, yes. I realize as a guy I have it much easier. My own wife would disagree with me on that point as well. 
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I have two toiletry bags. One of which is full of hair stuff. 
But if you can do it with all of your beautiful hair, I should be able to also.
I appreciate the way you laid this out for me.
Practical? Yes. Could I do it? No.
I will probably be at a mod, but don’t make me Disney math my way into a 1BR villa. This is supposed to be an “economical” trip.
(Is that an oxymoron?)
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Another practical option, which may or may not work for your hair, is to try out (ahead of time) bar shampoo and conditioner. My wife found a company that sells it and we tried several kinds before finding what worked for us. It takes up a lot less room for packing. (Most shampoo is mostly water by volume.) Search for Kitsch shampoo bar on Amazon to see what I am talking about. They have different types depending on your needs.
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This is key!
I carry an average of 1.5 quart size bags of 3 oz. toiletries per person. I have never been questioned. In fact I’ve only ever seen one sign that says 1 quart bag per person. Last trip I had 4 for the 2 of us. I wanted to make sure I didn’t run out of my sunscreen (Cancun after Disney). I didn’t even make it to the second bottle but that’s neither here nor there.
@TheSafetyLady Could you squeeze in an evening or morning of laundry? If so, you can limit clothing. as far as toiletries, my personal bag is a backpack or a small duffle. I can fit all of my stuff (excluding clothing) in it, including my straightener, medications, accessories, my extra pair of shoes (DH’s goes with a carry on), etc. DH and I can share 1 carry on and 2 personal bags for up to 6 nights. Haven’t tried longer because we can’t get away that long, lol.
I use packing cubes and roll a lot of my clothing. I bring a small bottle of wrinkle releaser. But I often iron in the mornings (only on vacation now though). As far as products, I think minimal. I don’t need all the different creams and such on vacation. I have my moisturizer/ sunscreen for my face and a travel bottle of witch hazel. My puffy eye cream and eye drops are small and I often put them in my make up bag if I can’t fit in the quart bags. Never has it been pulled. I keep the make up products to minimums. I use the small round plastic containers for hair smoothing cream and try to use sparingly. There isn’t anything that I can’t live without or buy at Disney. (except for DH meds and we never forget those)
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Good point. Instacart is your friend!
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Are we talking personal item or traditional rolling carryon for overhead bin?
I think either way the thing I skimp on is personal care products. Except for shampoo and conditioner I use what’s available to me.
And packing cubes.
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OMG it feels like straw almost immediately.
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Yes, especially in fair, consistent weather. Three pairs of shorts, one pair of pants if necessary, five tops, one swimsuit, one sundress if a nice dinner is in the agenda, sandals, socks/undergarments, foldable rain jacket. Minimal toiletries - I save samples from Sephora orders for travel and I have a tiny hair straighter if I need it. Maybe sunscreen wipes or stick (to avoid TSA size issues).
Wear sneakers, lounge pants and sweatshirt on the plane.
Of course I’d need a suitcase to bring home souvenirs.
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Well I would never!
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Fellow overpacker here 
. I briefly tried to curb my overpacking and checked bag reliance, but realized it was stressing me out way more than it was worth, and that I’m just not built that way. I get a lot of flack around these parts for my quantity of suitcases though 
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We? Give flack? I can’t imagine who would do such a thing. 
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My issue with checking a bag is the fear it will get lost. It only adds maybe 30 mins to the travel time each way to deal with a checked bag. So if you’re willing to deal with it (and pay if there’s an extra charge) I say do what you want.
I find it more stressful when I have no limits to what I can pack. I used to come home with just as much clean clothes as dirty, lol
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I feel this in my spirit. 
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Lay out the clothes you think you’ll want to bring.
Then put 25% back away.
My difficulty is shoes. 
It is possible to ship (full size toiletries) to your resort.
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I did 3 weeks in Europe with just a carry on …to this day I have no idea how I did that
I have done a 5 day trip to WDW with just a carryon when I flew a budget airline a stupid amount got luggage. I just wear the same things on multiple days. I’ve got toiletries down pat and I have curly hair too … just lots of little containers.
…and that Disney shopping bag in the way home usually doesn’t count against you 
(I now have credit cards for the 2 airlines I fly to get free checked bag …so I travel with a suitcase…and MCO really needs to fix there system! Took over an hour to get my bag last month)
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