Well, we kind of have that planned. You don't have to be super rich, just have to know your places pretty well and buy smart, maybe something that needs a little work.

We bought a house in Richmond, Indiana (more or less where I'm from) for $8000 - that was actually a mistake because it needed too much work, but the principle was sound.

Now we're looking for foreclosures in reasonable neighborhoods in Puerto Rico, we're probably going to build a house here in Budapest, and maybe we'll find something in Indiana in a few years. If you have modest houses in your places instead of putting all your real estate money into a new garage and a pool, it's totally doable.

A lot of not-so-wealthy people have a house in the North and one in Florida, after all.

Or you could sub-rent your place for a few months in winter and rent a place in a warm country. No wealth required.

I always wonder if there is a website to organize this. I have my own house but would like to stay here only 3 months a year and move for other 3 places elsewhere (fixed places). It would be a good idea for a startup.

There's quite a few websites that handle house swaps. Airbnb is also a good option if you have someone to manage the place for you while you're away.

I know someone who runs a hostel in New Zealand in the southern summer and travels in southern winter. Totally doable on a budget.