We did family vacations with my parents from the time I was born to the present, it just grew as our family grew, we got married and had kids. My parents still rent one huge (14 bdr) oceanfront house and everyone comes. There are 13 cousins age 15 and under - they have a great time.
When we had jobs as teens, we asked off for the week. It was not optional for us - beach week was important to my parents. There were other short vacations we could (and did) miss, but not beach week. The one time my youngest brother was a camp counselor and couldn't take off during the summer, the rest of us were in college and got out in early May so we went in mid May, once we got jobs it made more sense to go the week after Labor Day when we only had to ask for 4 days off (since we got the holiday). But we always went.