Building a Roof Top Pool
The following pictures show you the steps to constructing a usable roof top pool
Build the ground floor normally. If you want a two-story house on a foundation you will need to alter setHighestAllowedLevel in your userStartup.cheat file.
Build the first floor normally.
The second floor is the bottom and sides of the pool, and needs to be 4-clicks high - you will need to understand and use "boolprop constrainfloorelevation false" to achieve this. Cover the bottom of the pool in tiles, or the cheap aqua carpet works well.
There third floor can be a mix of full height wall, half height walls and 4-click high walls. The sides of the pool must be 4-clicks high. Cover the pool with a transparent (not invisible) tile, there is one at MTS by RGiles.
Roof/floor as appropriate. You will need to use "moveObjects on" to get the diving board and steps into position.
Sims can dive or enter the pool, but once in will need to use "Go Here" instead of "Swim Here" to move around - body skill is gained. When treading water there is a visual issue - both above ...
... and below. Odd light fitting that!