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Stunningly perfect white-sand beaches and crystal-clear turquoise water are all too easy to find in the Caribbean. Though the best beaches may be a huge part of why you’ve decided to look for affordable Caribbean real estate, they shouldn’t be the only thing that lures you to the islands.

If you don’t do your research, you could end up living on what you thought was the best Caribbean island to retire to, when instead it is far too populated with tourists and doesn’t offer the laid-back vibe you thought it would.

To find the best Caribbean island to live on for you and your family, start thinking about the things you know you can’t live without.

Tax Laws: Is It Easy to Buy, Sell

How easy it is for foreigners to live and work in the Caribbean varies.

When buying a property in Barbados, you won’t be able to pursue formal full-time work while on the island. And while you can obtain a homeowner’s permit in the Bahamas to legally remain on your property, you cannot work.

The Turks and Caicos, however, will give foreigners a 5-year visa as long as they can do work on the island that Turks and Caicos nationals cannot, making it one of the best Caribbean islands to live and work on.

Natural Attributes

Relocating to the Caribbean islands gives you plenty of opportunities to become one with nature, but what kind of outdoor activities do you enjoy? Many offer the white-sand beaches most people think of, but when it comes to diving or scuba diving, you may want to think past the pristine blue waters that come to mind.

In addition to gorgeous sandy beaches and the famous turquoise water of the Caribbean Sea, the Dominican Republic has mountains, deserts, and rainforests to spend adventure-filled weekends exploring. Other Caribbean islands with varied terrain include St. John, Jamaica, Dominica, and Anguilla.

Culture and Community

Building a new life in a different country can be difficult at times. There are language barriers and new customs to learn. The best Caribbean island to live on should offer the kind of transition that works best for you.

Do you want a large ex-pat community to make your move more seamless? If so, places like the Bahamas or Honduras may be right for you. Then there are the U.S. Virgin Islands, a popular destination for Americans due to their ties to the home country.


Do you enjoy the bustling sounds of a city that is always in motion? You may want to live in Santo Domingo or Kingston.

If you want an island life that is free from tourists coming for Spring Break or New Year’s, you may want to check out the outer islands. Spots like Bonaire and Honduras would be some of the best places to live, as well as South Caicos, one of the smaller islands that make up the Turks and Caicos.

propose in turks and caicos islands

Best Caribbean Islands to Live, Work or Retire

South Caicos

While most people may be familiar with Providenciales, the most populated island in Turks and Caicos, South Caicos provides the best opportunities for people looking to purchase Caribbean real estate. South Caicos is a short 20-minute flight from Providenciales International and has a much more laid back feel.

Purchasers looking for their piece of paradise won’t be short of options at Sailrock Living. A plethora of beachfront, overlook, and oceanfront homesites are available for sale, and Sailrock’s architects will work with you to design your dream vacation home. Purchasers looking for a vacation home that can generate revenue while they’re away may prefer the Sailrock Resort beachfront villas, while purchasers looking for more privacy may prefer the Private Peninsula villas, which offer seclusion and customization.

Ambergris Caye, Belize

Ambergris Caye has been attracting ex-pats for decades – for good reason. When you arrive, you’ll instantly feel the slower-paced Caribbean vibe that is so appealing. During the day, it is the center for ocean sports but at night, parties can be found all over.

Easy to come and go as you please, Belize’s domestic airlines frequently fly into Ambergris Caye from Belize City and there are water taxis available, too.

Roatan, Honduras

An English-speaking island, some of the most affordable Caribbean real estate can be found in this region, making it one of the best places to retire. For much less than in the U.S., you can have a two-bedroom beachfront home in a tourist-free neighborhood. Even if you only stayed here part-time, you could cover your holding costs by renting your place while you were away.

Expats enjoy the sound of gentle waves and palm tree fronds rustling in the morning and seeing the gorgeous Caribbean waters. Amenities are available here such as a pool and private docks and utilities are all in place. There’s also an international airport with regular flights to get you to friends and family or easily bring them to you.

Las Terrenas, Dominican Republic

While most Americans may have never heard of this beach town, Italians and French visitors have been coming here for decades, which explains the hint of European flair and international living it has. Smells of fresh coconut and saltwater mixing with espresso and croissants are common.

The Dominican Republic has a stable government, great weather, and a low cost of living. As a bonus, it is only a 3.5-hour flight to New York City. A great place to retire or relocate and raise a family, couples can live comfortably for around $2,000 per month.

Grand Bahama, the Bahamas

Often thought of as paradise, this is the place to go to see some of the most beautiful beaches. Extremely friendly to foreigners, there is no language barrier, low crime and it is just off the coast of Florida.

That’s the good news.

The bad news is that paradise doesn’t come cheap. Some of the nicest gated communities are located here and a medium-sized residence in one of them costs over $2 million dollars. A haven for divers, water sports enthusiasts, and those who cannot give up world-class nightlife and shopping, living here can be 50% more expensive than living in the United States.

Isla Mujeres, Mexico

Located off Mexico’s Caribbean coast and just ten miles from Cancun, it feels like another world entirely. There is no hustle or bustle and tourism is little to none. You won’t see cars on the road, but instead, golf carts – the preferred mode of transportation.

Enjoy temperatures in the low to mid-80s year-round and boating, swimming, fishing, snorkeling, or scuba diving. There’s also an underwater sculpture museum. Often residents are treated to dolphins offshore and sea turtles basking in the sun’s warmth right on the water’s surface.

Including rent, a couple can live well in Isla Mujeres for around $2,500 a year. Starting a new life can be amazing.

Find Your Paradise

The Caribbean islands offer various lifestyles to choose from and much more affordable prices. Finding the best Caribbean island to live may not always mean the cheapest, but it will mean happiness.