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I'd say to bring infant Tylenol, thermometer, teething tabs (if he's teething), nose bulb sucker, nail clippers, & baby monitor. Those are all things we've forgotten in the past and it was a bummer.

I would pack a few outfits in your carry on for baby and an extra for you and DH as well. You don't want to be stuck without extra clothes for everyone if baby gets sick while traveling or has a crazy blowout. I recommend bringing a couple extra gallon ziplock to put yucky clothes in so you aren't stuck with the smell on the plane. You can bring a purse as your personal item in addition to a diaper bag and pump for a lap infant (plus a carry on suitcase per adult plus the laptop bag can be DH's personal item). I recommend gate checking or carrying on everything you need if possible (especially the car seat). Also- don't buy diapers and wipes until you get there so you don't have to it to transport them. They are super bulky- 2 weeks worth of diapers can fill a carry on bag! I bet you can skip bringing a rock and play/ bouncer/ swing. Between hanging at the beach and being held by family, there won't be a lot of down time for baby to bounce. He can hang in the pack and play with toys if you need him to sit while you shower or something. Also- I usually don't bring a changing pad when I travel because they are pretty bulky. I just use a recieving blanket folded in half.

We loved this when we traveled - you can have it shipped to your family's house. It folds flat and super easy to travel with.

Mommy's Helper Drain 'N Dry Bottle Drying Rack https://www.amazon.com/dp/B000056J1C/ref=cm_sw_r_cp_api_LC6rxbXPRBT4H

We keep a Dream on Me mattress and sheet at each grandparents house to stick in the PNP - DS always sleeps super well with it.

If you bring the video monitor, get the Velcro picture hanging command strips - makes mounting the camera a breeze without damaging walls.

Wear the baby through security in an Ergo. Check everything else through to the final destination. Also bring a washcloth - the baby ends up laying and sweating against your clavicle in the Ergo and a washcloth as a little pillow will keep both of you more comfy.

Pack a blanket or wear a shawl and you can lay it out if your baby needs a place to roll around on a layover. Shawl also works as a nursing cover. I also packed a large zip up hoodie of DH's and would wear it over my pumping rig when I had to pump at the airport.

Carry a normal size pack of wipes - not a 10 sheet travel pack - you use them for everything.

We had massive poop blowouts up the back on the plane for some reason so our solution on the trip back was tucking a cloth diaper up the back of DS' diaper inside his sleeper (we dressed him in footed sleepers for travel) to catch the poops.

The bathrooms with the infant changing table is usually towards the front of the plane but check Seat Guru to make sure and try to sit near it.

Make a diaper go bag for the plane - gallon size Ziploc bag with a diaper, the flimsy travel pack of wipes, a tiny hand sanitizer, and a onesie, plus a quart size Ziploc bag for disposal (the flight attendants get stanky about diapers in the trash) - and tuck that into the seat pocket so you don't have to drag the whole bag to the bathroom with you.

For diapers, I always brought at least one for each hour of the flight.

In your carry on, bring some small bags to use as garbage bags. If you have a serious blowout, you'll want to bag everything and put it in the garbage that way, plus you might accumulate trash or need to put something back in your carry on to launder.

I didn't see sleepwear on your checked bag list. I also typically will buy things at the destination or send them ahead via an amazon order.