One of my friends taught at one school and her two children were at different local schools. They struggled to find two weeks when their school holidays coincided. This was when 'Mill" holidays still took place in our area. The holidays were staggered with local towns starting their break as others returned from theirs. It worked well for us because our break was the last week in June, first in July. We had cheaper, quieter holidays but didn't work for my friend's family.
I retired four years ago but when I was working I knew a number of children from Irish traveller families who were taken out of school in June, returning mid or late September. During the extended break, they travelled using the caravan they lived-in, or kept at the side of their house. Similarly, children with family in Pakistan were sometimes taken out for up to 12 weeks for an extended visit to their family homeland.
I've little sympathy for the father in the current case, who took his child out of school for two weeks to go to Disney World. He could have afforded the premium charged by holiday companies. I sympathise with people whose work patterns don't allow them time off during the set school holidays. I'm sure most head teachers would be sympathetic to that kind of situation, or family ill health/bereavement issues.