Seeking Advice on Best Long-Term Investment Locations in the USA or Caribbean for STR

[Richard Foltys]

Hi everyone! 👋

I'm Richard from Toronto, Canada, and I'm looking for recommendations on the best locations in the USA or the Caribbean to invest in for a long-term hold (10-15 years). I'm especially interested in spots with strong short-term rental (STR) demand, where the laws are favorable to investors.

I have around $250,000 USD to put down as a deposit, and I plan to finance the rest through a mortgage. Ideally, I’m looking for areas with a mix of:

1. High occupancy rates for STRs (Airbnb or VRBO),
2. Solid potential for appreciation over the long term,
3. Investor-friendly regulations on short-term rentals.

If anyone has experience with markets that fit these criteria or knows areas where STR is thriving with good investor laws, I'd love to hear your thoughts. Thanks in advance for any insights or advice! 🙏