Booking
I rented points from David's in mid March for Aulani in December. It took a day to hear back. I hear about 7 or 11 month booking windows, but I have no idea how that works or if it is hard to snag rooms this way. Either way, I was happy to get exactly what I wanted so quickly. Rack rate for Aulani was $3271 for 5 days. I paid less than half that using points. David's was prompt and answered all my questions and put in my room request with the owner.
Now that I've been to Aulani. 5 days is waaaay to short of you have preschool age children. There was so much to do for this age range. We are already thinking of going next year for a few more days.
Flights
Husband and I signed up for Hawaiian airlines credit cards. With the bonus points and the 50% off companion flight offers we were able to cobble together discount and points to buy flights for the three of us (me, DH, and DS 3). We just spent $1000 on each card within the first 3 months of opening the card and immediately paid it off once the points were credited. We paid the upgrade fee to sit in comfort class. Soooo much leg room! It was nice to have plenty of space with a toddler who needs to get up often to use the restroom. Note: We didn't buy all these seats in one transaction. Husband had 2 one way tickets and the kid and I flew as a round trip. We booked early enough to still get seats together, no problem. Note: I am a big time 0% APR credit card hopper due to some unexpected family law costs a few years ago that needed to be paid with a credit card, so I am used to playing the credit card point game. I can see this being a little bit of a nuisance to track...but it was well worth it for me to get discounted or free flights.
We debated on the bringing a car seat but ours are really wide and bulky. So we opted to buy a CARES harness. I got one off eBay for half off and it was awesome. It's a little seat belt attachment that converts the airplane seat lap belt into a harness. Very easy to install and gave me piece of mind in regards to safety on the plane without a car seat.
Rental Car
I made a reservation through Costco months before the trip for about $500 for the 5.5 days. I checked back often to watch for price drops and ultimately got a medium size car from Enterprise for $200 a month before the trip. My final price was a little higher because I had to rent a car seat.
Budgeting
I am a big Target shopper and a coupon clipper. I used my free Target gift cards (from buying my weekly groceries) and Redcard (5% off) to slowly, over the course of many months, buy Disney gift cards. Target also has a December 20% off Target gift card sale so I bought the max amount of those and then turned around and bought Disney gift cards with the Target cards. YMMV, Target recently changed their policies. There's a disboard forum that talks about the discounts you can do to buy gift cards. I found it helpful. Saving a bit over time was really good for me. It was nice to have over $600 in gift cards to use at Aulani without having that hit my bank account all at once. Note: Again, we also have
Disneyland passes. So I knew I could spend it there if I didn't use all the cards at Aulani. Second note: I say "cards," but ultimately I consolidated them onto one card. Very easy to do online.