I actually took a team to an off-season ski chalet in Chamonix one summer, and it was surprisingly affordable. Airfare included, it came out to less than we'd pay for cubes in LA. Possibly even less than $200/desk/month, considering the place rented for $800 euro per month and slept 10 comfortably in 6 bedrooms.
In SE Asia, I guess you could go 2 ways with pricing. You could look at what the backpackers pay (~$10/night or $200/month for a room), and go with something comparable so that you'd get some overlap (and thus end up with Swedish girls hanging out at the pool). Or you could go for the "Surf Camp" model, where you charge $4k/week to people who have too much money. Personally I'd probably lean towards the first model if it were up to me.
Mostly I'd be looking for something that paid for itself, kept me on the beach, and kept a bunch of interesting people around.
While I wonder about the price (could bootstrapped startups afford it, especially counting the air fares?), I can see this being very successful.