I did this and also spoke with local owners on one of the other islands and occupancy was 25+ nights a month. 

Off the top of my head...big destination areas (I moved in 1992 so these may be dated) aside from Big Bear,Lake ArrowheadAny proximity to Disneyland...and potentially Knott'sPalm SpringsSalton SeaAny beach area (Fiesta Island down in San Diego is often overlooked...and pretty much across from Sea World)Lake Isabella/Wofford Heights/KernvilleSolvang (go visit the Good Life and tell them I sent you - I graduated high school with one of the owners)Catalina Island?

I would move to the islands open a bar, run poker events out the back side.

You have to realize, with all of the growth in Belize over the past few years, there has not been a new hotel built in over 14 years, and the actual number of rentable units on the Island has actually decreased over that time.  

In NY, Westchester, Rockland, Long Island and surrounding suburbs.

Galveston Island, TX attract many tourist. 

In Staten Island, they actually pay more than the market rents because they need housing.  

I currently live in the Chicago suburbs but looking into purchasing a property for short term rentals in St Pete Beach, FL or Treasure Island.

HSBC can help you get checking accounts setup in almost any country.We are taxed on our world wide income in the US, but that’s not that big of deal, as we have treaties with other counties to help avoid double tax, and you can always setup up IBC in Cook Island, or St Kitts & Nevis, thus off shoring the income earned outside of the US, if you bring it home you will have to pay taxes on it.

@Mickael Castillo and @Tanya Solomon... we have a Coffee With Investors meetup the 2nd Saturday of every month in Delray Beach.