We mostly worked around school schedules, but in middle school my son was in a charter school. We pulled him out twice for extended vacations. Rule was all homework had to be turned in when we got back PLUS he had to write an extra paper or do an extra project. One trip was to Hawaii, another to Disney. Hawaii involved extra work around volcanoes and Hawaiian culture, and Disney's was on rocketry as we took a side trip to NASA. I like a vacation to be a vacation-not stressing because I'm standing in line of hours at a time, smaller crowds, etc., so going at an off-peak time has other benefits. He's learned more outside the classroom than he ever will inside one.
For my son it was no issue-he was still well ahead of his class. We didn't do it in High School-too many rules about unexcused time off as well as the caliber of his classes. Taking all honors and A/P classes doesn't lend itself well to taking time off. Decisions should be made on a trip-by-trip basis and the child him/herself.