A Safe, Welcoming Country

What Should You Look For In A Caribbean Home For Rent Long Term

It’s the ultimate dream: steal away from the crowds and escape to a secluded island where you can be free for months on end.

But are there things you need to check before you go?

First of all, check to see how long you can stay on the island without compromising your residency at either location.  US Citizens can be out of the country for 12 months; any longer may result in a loss of residency status.  Canadians can be out of their country for a maximum of 182 days in a year.  You can travel outside the Netherlands for 6 months in a year.  Check with your country before you look at Caribbean homes for rent long-term.

Then, there is the length of stay wherever you are going.

What Caribbean Islands Allow Long Term Rentals in The Caribbean?

Since the COVID-19 pandemic, a select number of Caribbean countries are offering Digital Nomads visas.


Anguilla’s Digital Nomad Package launched in August.  Designed for people who want to get away from it all but stay connected to everything, the program costs $2,000 per person and allows you up to 12 months on the beach.  Internet is fast and the island has excellent cell phone coverage, so you’ll be able to work hard and play hard whenever you choose.

Visit the Anguilla tourist board’s site and search for Bask in the Sun to find details on the Digital Nomad package.

With just 3 cases of COVID19 since the pandemic began, Anguilla is an appealing destination for people looking to stay safe while still enjoying day to day life.

Antigua and Barbuda

In October, Antigua and Barbuda announced their Digital Nomad Residence Program.  The program allows people to live and stay for up to two years as long as they can prove they can support themselves.

The country has good wifi and cellular coverage, and has had just 100 cases of COVID since the pandemic began.

Proof of health insurance, and proof of income are required to apply for their program.  Visit the official Antigua Digital Nomad website here.


One of the Caribbean’s more populated islands, Barbados is also offering a one year digital nomad visa, first announced in July. Call the Barbados Welcome Stamp, it allows people to work from the island for up to one year. The application costs $2,000 and you must prove income of $50,000 and the means to support any dependents in your application. They have had a moderate number of COVID19 cases, and 7 deaths.


If money is no object Bermuda may be a good choice for you.  Their newly-released Global Entrepreneur Work Permit allows you to work or study on the island for a year, with unlimited entries and exits.  Once you’ve cleared your arrival and processed your application, you will still be required to wear masks and physically distance while on island, but you can work easily from just about anywhere on the island.  New Yorkers will not be required to quarantine when they get home, nor will UK residents. If you do test positive while on island, they have a unique way of managing the situation:

Anyone who becomes COVID-19 positive, or whom health authorities believe could be positive, will be fitted with an Aqua electronic bracelet to assist with isolation/quarantine.

Now that you know where you can go, what else do you need to consider?

House Rental in the Caribbean

The best Caribbean beachfront villas come with everything you need to get started.

  • A point of contact on the island
  • Fully equipped with internet and phones that work on-island
  • Easy access to supply delivery to get you through any mandatory quarantining.
  • A pool, for days when the ocean is rough and you just want to laze around on a lounger 🙂

It’s also important to have a good understanding of the island’s vibe.  That sounds a little subjective, but spend some time doing research online.  Is the island friendly to long-term visitors, or does it cold-shoulder them?  Will you feel welcome and make friends easily, or will you be an outsider the whole time?  Look for islands where everyone is welcome.

Consider Accessibility

Do you plan on having friends come and join you while you’re staying at your villa in the Caribbean? Then you’ll want an island that is easy to get to.

Is privacy important to you? Are you looking to get away from large groups of people gathered tightly in one spot? Then an island that is more difficult to get to will ensure seclusion.

It’s a personal choice.

Choose Your Long Term Caribbean Rental With Care

Like most things, it’s best to find rental reviews from others who have stayed there before you. Get a sense of what it is like to spend an extended period of time at the villa. Did the guests find lots to keep them busy or were there amenities lacking that might have created a comfortable nest? What is included with the rental – will you need to bring a lot of things from home or purchase several things while you are there? Figure that into your over all cost (and convenience factor!)

At a minimum, make sure that Public Health has certified the villa or home to be up-to-date with COVID cleaning regulations. If you are not sure, reach out to the public health department on the island you are looking at.

Finally, consider things to do on the island you are looking at. Are there enough adventures to keep you from getting cabin fever? If so, you’ve found a Caribbean vacation rental for long term fun and pleasure.