How is it possible to create a hole in an overlay where you can see through to the actual website?
No. This is not possible, not in most browsers.
CSS Masking
You can use masking, if you are interested only in new browsers:
Specs: http://www.w3.org/TR/css-masking/
Compatibility: http://caniuse.com/css-masks
Border / Outline
You can also use border or outline css properties if you want to create simular effect and set color of them to transparent so it looks simular.
Position Absolute
You can also use position:
// top div is over child of this one
Transparency and elements
http://css-tricks.com/non-transparent-elements-inside-transparent-elements/
http://css-tricks.com/examples/NonTransparentOverTransparent/
-- this is not what are you asking for, but it can helps you :)