Originally Posted by windhund

Hard to give specific recommendations without knowing the length of the trip and about how many points you want to give them, but generally booking 5 night stays (since you get the 5th night free with bookings made with points) will be the best use of points.

I second SacTownGuy: if a room with a view is important to them, definitely pay for the upgrade when you make your booking so it's guaranteed. If you're unsure about what room types are best, I would suggest calling the hotel. The names and pictures sometimes do not make it easy to tell just how much of an ocean view you'll get.