Have you thought about trying for some credit card sign-up rewards card bonuses to take the edge off of the costs? Last year using the Barclay Arrival (and my Disney Visa) I racked up a few thousand $ in rewards.
Just the Barclay rewards travel reimbursement feature erased about $1250 in ticket costs.
I am just about to start doing it again, hopefully with another set of Barclay Arrivals for my DW and I, plus with Chase Sapphire and possibly Ink cards. My ultimate goal is to get super cheap or possibly near-free APs so that I can use them over 2 summer trips in 2019 and 2020.
If possible, I may also try to get a Marriott rewards bonus to get a “free” stay at the Swan or Dolphin too. (Not really free, since using points to stay free means you still end up paying almost $50 a day for resort and parking fees, but still a good deal.)
Since as a rule we do not carry credit card debt from month to month, right now I’m going over my timing so we can earn the sign on bonuses sequentially without spending money on anything we don’t already buy. (Plus, I want to get this all in within a year, since I get cards with no annual fee in year 1 and want to avoid getting hit with those fees next year.)
What is really kinking up my plan, though are my kids’ summer activities - DD11 takes a few classes at the local high school each year right after school ends, then my DS15’s HS marching band camp takes up about 10 days in August. Plus, this year he went to a drum major academy and is already talking up going again next year. Squeezing 2 trips in within 12 months with so little calendar time open is proving difficult.