18500 will always work in the space of 3xAAA, and provides about 60% more energy than good NiMH cells.
Not always, it really depends on the light.
Take
this one, for example.
A 3AAA carrier is slightly longer than a 18500; it doesn't matter in some lights, but this one needs its contacts stretched to reliably contact a 18500.
Also, it is completely unresistored. I did
some testing in my review of it, and current draw from a fresh 18500 is way too high for those poor LEDs.
In other words: if a light is resistored, then it's probably ok to run it from a 18500 or 18650 if it fits. If it's not resistored, doing that is asking for trouble.
It would be easy to build a spacer containing an appropriate resistor, though, which would also solve the problem of the shorter length of the 18500 cell.