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Short-Term & Vacation Rental Discussions

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Derek Davis
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Vacation/ Short Term Rental in the Caribbean

Derek Davis
Posted Jan 24 2023, 11:28

I am interested in buying a beachfront condo in the Caribbean to use as a Vacation property/ Short term rental.  The long term plan would be to hold the property as a retirement destination for longer stays after it is paid for.  Does anyone have experience doing this?  I mostly would like to speak with someone about how they determined which islands they considered investing in and which islands they ruled out and why? Looking for just general advice or conversation on restrictions related to foreign purchases, short term rental data for certain areas, lifestyle and convenience as a retirement location, etc?

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Michael Baum
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#2 Short-Term & Vacation Rental Discussions Contributor
  • Olympia, WA
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Michael Baum
Pro Member
#2 Short-Term & Vacation Rental Discussions Contributor
  • Olympia, WA
Replied Jan 24 2023, 18:43

Wish I had an answer for your @Derek Davis. The easy thing to look at first is which countries allow investment purchases for real estate without actually living there. There are restrictions in some countries. That will narrow it down.

Essentially you just look at where people go the most. What is the crime rate? Bermuda looks good on paper, but the crime rate is outta sight.

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Brooklyn McCarty
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  • Investor
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Brooklyn McCarty
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  • Investor
Replied Jan 25 2023, 03:09

Use Google and the enemy method. Look at other properties for rent in the area, reach out to those hosts. 

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Jeff Wagner
  • Real Estate Broker
  • St. Thomas, USVI
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Jeff Wagner
  • Real Estate Broker
  • St. Thomas, USVI
Replied Jan 25 2023, 05:11

I may be biased, but often times people forget about Puerto Rico and the US Virgin Islands.  In my view, risk is reduced by owning in a US flagged territory.  As example, in the USVI we have fee simple ownership, title insurance + contract and closing process similar to the mainland.  Puerto Rico has more nuances, including spanish language long term ground leases, but is also US territory.  I personally evaluated several central american and caribbean destinations before ultimately settling on the USVI.  To add to @Brooklyn McCarty's point, AirDna seems to be ok for here as well, easy way to check rough numbers.    

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Michael Evans
  • General Contractor
  • Palm Desert, CA
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Michael Evans
  • General Contractor
  • Palm Desert, CA
Replied Jan 25 2023, 05:18

Keep in mind that each island is actually a country. You need to do some traveling and actually visit and spend some time there. I would do some due diligence on an island/country friendly to the US, uses the US dollar as their currency and is not prone to political upheaval. Staying away from socialist government ruled countries would be my main concern.

Good luck!

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Aaron T.
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  • Developer
  • Aguada, PR
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Aaron T.
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  • Developer
  • Aguada, PR
Replied Feb 6 2023, 05:33

We have STRs in Puerto Rico. Buying here is much like the mainland, because its a territory. If you buy in a foreign land, you will be subject to their local laws, etc... some places to buy you must be a citizen, some dont offer financing to foreigners, etc... just be prepared and knowledgeable on what you are getting into. 

If its a place where the government is not stable, just remember they can come take your land and property with no recourse to yourself. Its just how it works in Latin America. 

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Kathryn Morea
  • Developer
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Kathryn Morea
  • Developer
Replied Feb 6 2023, 07:17

We have STR's in Puerto Rico. There's lots of advantages to owning in PR including tax credits for hospitality projects and virtually the whole island is an opportunity zone. Keep in mind that prices here have risen over the last couple years, just like most of the mainland. And you will be searching for the same product that most other people are also looking for, so it's competitive. DM me for more info.

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Account Closed
Replied Feb 21 2023, 21:08

You can do your research through Google. Look for your competitive properties in your area and have discussion with their host.

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Junior Jaquet Hernandez
  • Real Estate Agent
  • Dominican Republic
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Junior Jaquet Hernandez
  • Real Estate Agent
  • Dominican Republic
Replied May 20 2023, 23:12
Quote from @Michael Baum:

Wish I had an answer for your @Derek Davis. The easy thing to look at first is which countries allow investment purchases for real estate without actually living there. There are restrictions in some countries. That will narrow it down.

Essentially you just look at where people go the most. What is the crime rate? Bermuda looks good on paper, but the crime rate is outta sight.


 Dominican Republic allows you to purchase properties without living there, no restriction for international investors and also taxes are very low comparing others countries and by the way you can get it rent it fast.

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Replied May 21 2023, 04:29

The Dominican Republic has laws that ensure foreign owners are treated (under the law, at least) the same as citizens/residents. If the cost of living factors in heavily to your calculus, consider the non-touristy areas of the DR. That's where we bought our home.

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William Arrington
  • Gainesville, VA
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William Arrington
  • Gainesville, VA
Replied May 23 2023, 04:19

I looked into this last year. The British islands charge a crazy tax on your purchase if you're not a citizen. I can't remember the percentage but it was enough for me to just close the webpage and realize I would never buy. I then focused on my favorite place in the world St. John. All I can say is beware the hidden costs. Places like this grow like a jungle and you will pay an enormous amount to keep the property up (you're not there and have to hire a company full time or its built into the (HOA... not always called this) All of these are a lot more than you think they will be. Materials are also an issue... not like the mainland where you can just run down to a massive big box store and get whatever you want. By no means am I telling you not to do it... I didn't look at all the islands but a handful that were all pretty close to st john but prices are pretty elevated right now and even the math on a flood-damaged 6 bedroom 6 bath with a crazy view and me doing 50% of the work was still not workable. Also remember that its normal for something to take a year or even more to sell on some islands so you might not have an easy way out if its not working out. Condo fees in st croix run between $750 and $1100 on average per month. Do your diligence and then have it checked again.... and if you get one... send me pictures... I am always looking for new vacation spots.
https://www.seaglassproperties...
to get you started on your research.