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I keep a checklist. I pull it out for every trip. It makes me feel slightly more in control!
I also have a travel med bag which goes in every trip
I'd leave as much spare stuff at you can at the beach house and then make a comprehensive list of what you keep there so you don't double up!

If it works with your destination, order diapers, wipes and snacks to meet you there.

We usually pack our family in two bags and on the way home one bag is stuff that's still clean/been washed and the other is only dirty clothes (shoes go with dirty clothes and toiletries with clean.) One bag goes upstairs and one downstairs. Having a drawstring sack on our trip for laundry really helps.

My carry on is a zip top canvas bag (lands end I think) and then in doubles as a beach bag. We buy cheap beach toys and leave them behind, it's worth the $3-5 not to have to worry about it. I have a ton of little zipper bags and I use them to separate everything. I even stash travel toys in them, one activity per bag so it's kind of like they are gift wrapped, she doesn't know what it is until she opens it so she's not digging through and vetoing things because she's grumpy. Target has some that are a bit bigger than a sheet of paper that are clear plastic with designs in the dollar spot for $3 and I love them for a mini diaper bag, I throw in a disposable changing pad, two diapers and wipes and then it doubles as a wet bag of need be.

I think my biggest tip though is screen time limits go out the window during travel to and from!

@Cole: great tips, especially about having things delivered. I also do one suitcase of dirty clothes and one suitcase of clean clothes for the return trip, it makes unpacking so much faster.

Since you are going back and forth to a beach house (and I assume you have laundry access), I would leave as much as possible there, especially for your LO. If you can, leave a few days worth of clothes, toiletries and toys.

We have a packing list and packing cubes. Each person in the family has a different color packing cube set. We have a 3-piece Samsonite set. The boys share the medium suitcase and DH and I share the large suitcase and the carry on is for miscellaneous convenience items. For instance I always carry command strips, a battery powered push light, the white noise machines, thumbtacks, clear packing tape, the baby monitor, a small extension cord, and spare blackout curtains. I've push pinned blackout curtains over windows and set up weird sleep spaces everywhere.

If you're driving I like to pack things like dry food or snacks or toiletries or shoes in sturdy reusable shopping bags because you can just throw extra things or forgotten things into the sacks and then it's easy to unload them later. For toiletries I just keep a full size thing of toothpastes and brushes, deodorants, shampoo, conditioner, face wash, hand soap, and a bar of soap, a hairbrush, plus baby wash and a bottle of Cetaphil lotion, sunscreen, dishwasher pods, a new sponge, bottle brush and straw brush, a bottle of dish soap, and Tide pods for the whole family in a sack. I would just leave that and a similar bag of medicines at the beach house or your car to always have. Those are things I'm fine having duplicates of bc I will always use them. I always take garbage bags and gallon ziploc bags with me. Dirty laundry and beach/pool stuff like jumpers or vests or water shoes all go in garbage bags. We take one small milkcrate of toys and books. I put DH in charge of electronics and he wrangles all the tablets and laptops and chargers in his laptop bag. We got a Verizon wifi jet pack for our last road trip and it was a godsend.

On road trips I like having a cooler with ice with fruit and veggies and drinks and a sack of individual size snacks accessible to me. Everyone gets a full water bottle and I also find having bottled water or a gallon jug of water in the car vital. I like having a playlist of our kids fave songs loaded on both me and DHs phones and play them over Bluetooth for the kids - that keeps them happy for quite a while before we need to break out tablets.

We have a minivan and we like to orient our stuff in such a way that we have a small space in the trunk that fits a changing pad for diaper changes on the go.

We also take the baby's PNP mattress with us to keep him comfy.

Yes on the extra ziplocs and packing cubes! And packing up dirty laundry separately. Or better yet, do wash at the beach house before returning if time allows.