To get this trophy, you must build hotels on two different monopolies. Start a two player game and play both players. Get player one two monopolies and build them up to hotels to get this trophy. If you need to, simply trade money from player two to player one.
While the wording suggests that you can have the hotels built at two different times as long as they are on different monopolies, that might not be true as the wording for trophies in this game aren't always the best or most accurate.
Because of its nature, this trophy can pretty easily be done alongside the "Out of Stock" trophy and the "Business Master" trophy.