There are strong disputes on the pages of religious publications about the over-the-top vacations people take. Those in favor basically say "It's MY money and don't tell me what to do with it". So there!!!
I get it.
But there is another angle. Actually - many other angles. One is that it turns out that it is not your money. My money is not my money. Like many things in life - it is an optical illusion. It is actually Hashem's money that He gave me with His Infinite kindness in order to use to serve Him and make the world a better place. That is a different perspective. But I will be honest [in Modern Hebrew they say "עם יד על הלב"], I know very few people who really view their money that way [despite their protestations to the contrary]. People feel very strongly that the money is theirs and fiercely protect it and try to increase it. I get it. I suffer from the same illness. I need a refuah .... and am not alone. It is not mine. Nothing is mine. I breathe approximately 22 thousand times a day and each and every breath is a gift that I don't deserve and take for granted. One day, my breath will be taken from me and at the same moment - "my" money.
So the first question is if these vacations are the will of Hashem. If they are - גיי געזונטעהייט ["party hardy" in Yiddish]. If not - ...... Of course the answer would depend on the vacation and the circumstances around it. Sadly, I am not aware of Rabbonim receiving shylos about whether to go on a vacation in Cancun or anywhere else. Instead, people ask world changing questions such as whether Quinoa is kitniyos. If when I get to shomayim the first aveirah they catch me on is eating Quinoa on Pesach - I am in good shape. Sadly, I don't eat Quinoa on Pesach - or ever. Mostly b/c the spelling of the word annoys me.
Something else to consider is whether the teachers of your children have enough money to make Pesach. Many of them are being paid far less that what they need to cover basic living expenses. Giving to teachers is not mere Tzdaka. It is common decency to make sure that the most idealistic group in Klal Yisrael [besides possibly the Chabad Shlichim in places like Nepal] who are insuring OUR CHILDREN with the most important thing in life - a Jewish education - are taken care of, before we live in the lap of ultra-luxury. I am no longer involved in chinuch [probably b/c, among other reasons, I am really bad at it...] but when I was, my "salary" was less than my rent - and I didn't own an apartment and my wife didn't work. Then came the Yomim Tovim with the myriad of expenses Baruch Hashem and there were no bonuses or anything of the sort. The expectation was that just like I made it on starvation wages until now - keep it up. [Although I must admit that I WAS asked to increase my hours without receiving a raise of any sort]. One of my employers told me that not one employee lives off the salary he is paid. Wow, maybe do something about that??
Thankfully, back in those lean years - Hashem helped [His angels looked EXACTLY like my parents]. But when it comes to caring about other Yidden we drop the Bitachon thing ["Hashem will help you"] and dig deep into our own pockets. Bitachon is for ourselves [among other things to believe that the money we have is from Him and act accordingly] - not in order to shirk basic obligations.
Brought to you by the "Society For The Preservation Of Mechanchim And Mechanchos Of Am Yisrael".