If you haven't booked your vacation spot, don't wait!! It's easier to find what you want the earlier you start.
I recently organized a family vacation for my parents, my siblings and their families and our family. If you are working with others besides your own family, take into consideration location, location, location. Our family is spread out and we chose a place somewhat between us.
You also need to consider special needs - sleeping arrangments - couples, children, single adults, gender; pets coming along; price; interests of those coming along (golfing, tennis, etc.); and the dates when everyone is available.
If you have friends who have been to the location you chose, get their advice. I looked online for suitable housing. Needing a place that accepts dogs narrowed down the field. I looked at the "touristy" sites as well as places offered by individual property owners. And a couple of siblings offered websites to look at, as well.
We had to weigh price with amenities - we could get a couple of townhouses, with pools, tennis and golfing. But we chose a large house instead so we could all be together and have a common place to eat, play games, etc. It was a little more expensive, and there was no pool, tennis courts, or golfing on site, but they are available nearby. But there were other amenities we hadn't counted on - a pool table, foosball table, and horse back riding.
I found it very helpful to talk to people onsite at the various locations we were considering to get all our questions asked. You certainly don't want surprises when you arrive!
I communicated with family members via email at each decision point so we could make choices in a timely manner. It took a couple of weeks before we waded through everything, but everyone seems to be happy with the choice. If you are just planning for your own family, it will be much simpler!
Thanks for visiting my blog. Hope you find some helpful hints for organizing your time and space. My passions are to help you make home a refuge instead of a crisis center, and to help you function in peace rather than chaos - at home or at work. I have switched my main blog to 1-2-3 ... Get Organized on WordPress, so please visit me there.