You can check VRBO it is a website of private residences for rent usually costing as much or cheaper then a hotel, and many homes have pools. Re Mexico Carribean latin America, please be aware of the crime rates you must stay in a place that also has private security. In many of the countries in latin america and mexico tourists are walking targets. Wherever you go, have fun and be safe!p.s. Mazel Tov!(BTW how about a vacation villa in Eretz Yisroel i am sure outside of yerushalayim you can find a residence with pool.)