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! 🙏

[Travis Timmons]

You have to do your own research and form an investment thesis. The days of following the crowd and making easy money are over. 

I think that we are in a "what can you do that is really hard?" real estate market right now.  One form of that is finding a specific niche subject matter expertise...something like an ice fishing cabin that those of us who don't know a thing about the category would never think of investing in. Or it could be something like dialing in on and area and figuring out exact requirements for parceling off additional lots - find an old house that nobody wants on 5-10 acres. Fix it up and parcel off the additional lots to either sell or build. 

Other ideas that have captured my attention are finding a 4 bed/1.5 bath house that has room to add a stand up shower to make it a proper 4/2. 

I'm spit balling a little, but you have a create a deal to get the outsized returns that STRs offered a few years ago.