One tip I used when my DS was 10 months old: we were staying at a Ritz resort in Maui (we lived on Oahu), and they brought us up a high chair. I took a bedsheet (called housekeeping for an extra) and spread it under him every time he ate. Then I could shake it out to lessen the crumbs on the carpet! If you have your condo you can get an extra sheet and do that, then wash it every day or so too. It helped us and them.
I used to have a nice little plastic chair thing that attached to a regular chair - wish I could remember what the brand was. We'd take it to relatives' houses when out - it had a tray and was very safe - it had a strap to attach both under and to the back of a regular dining chair. I don't know if they make those anymore. It also folded up very nicely.
Definitely call the resort ahead of time, or look into a travel one maybe.