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Looking at a Caribbean Getaway? Try a Timeshare

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Posted on December 21, 2021

We’ve all seen the pictures. Images of azure blue water lapping up against the white sand beaches. The sunny days and always warm weather. Amazing natural scenes of palm trees leaning over the beach. Wonderful food and unique cultures. The Caribbean has everything you need for an amazing timeshare getaway.

So, what do you do now?

First things, first. What island do you want to visit? The Caribbean as a region covers an estimated one million square miles with about 700 islands, so you have some decisions to make.

Fortunately, many of these islands are uninhabited or just too small to consider. But that still leaves a large range of destinations, so let’s look at a few items you may want to consider.


While English is spoken throughout the Caribbean, there are places such as the Dominican Republic that can offer more of a challenge, especially if you like to head out off the beaten path.

Any possible language barrier won’t be an issue at your timeshare resort in the DR, especially at timeshare resorts such as those in the Lifestyle Holidays Vacation Club. But the more adventurous you get with your itinerary, the more likely you may run into issues.

Islands which are territories of the U.S. or with affiliation to the U.K., such as the U.S. or British Virgin Islands, Grand Cayman, Jamaica and Barbados are good to go. Even islands with French or Dutch heritage like St. Maarten and the ABC islands (Aruba, Bonaire, Curacao) are not a problem.  

Philipsburg St Maarten


This is one area you really don’t have to worry about, since the islands take U.S. dollars nearly everywhere. Since the U.S. Virgin Islands and Puerto Rico are U.S. territories, you will use your U.S. dollars just as if you were at home.

Sometimes it can be better to use the local currency. The Cayman Islands is known to have a stronger dollar than the U.S. dollar due to its status as a tax haven.

Canadians may have more of a problem, especially if Canadians are traveling to the U.S. Virgin Islands or Puerto Rico. Canadians traveling to Cuba will also run into currency difficulties and need to exchange into the local Cuban currency.

One rule of thumb is to always have some small amounts of local currency with you in case you venture into places such as local markets or want to tip. Also – using a major credit card will take the hassle out of spending money and many no longer charge international transaction fees, but best to check with your card provider.


For American travelers, you’ll need your passport to travel to the majority of Caribbean islands. Notable exceptions are the U.S. Virgin Islands of St. Thomas, St. John and St. Croix, along with Puerto Rico.

Some islands require a visa prior to travel, so check with the government website of the island you want to visit to review any potential visa requirements.

COVID Passport Image


Yes, the pandemic is still an issue, but fortunately due to vaccination rates this isn’t the major problem it was at this time last year. Many islands no longer require quarantine if visitors can prove their vaccination status, but most still require a negative PCR test prior to arrival regardless of vaccination status.

The vast majority of Caribbean nations are well under their previous peak of COVID cases, so this doesn’t appear to be a problem as of the time of this writing. Reuters has an excellent website tracking the case levels on each island as well as throughout Latin America.

The larger issue is returning from the islands back to the U.S., since the CDC still requires a negative COVID test taken within three days of departure back to the States. Many resorts offer onsite testing facilities, so best to check with your resort and the CDC website before leaving the U.S.

Type of Experience

hammock on beach

Ah, now we are to the good stuff. Are you more of a beach person, or would you rather explore into the mountains? Want a more diverse cultural experience? How about snorkeling, which we have covered in a previous blog post here.

Contrary to some beliefs, not all Caribbean Islands are the same. The Dominican Republic has the highest mountain in the Caribbean, Pico Duarte at over 10,000ft. Jamaica has the fourth highest, Blue Mountain Peak at about 7,400 ft. Conversely, Grand Cayman is flat as a tack.

Puerto Rico has incredible history dating back to the 16th century, with the El Moro fortress protecting San Juan since 1539. The island is also home to the tropical rainforest of El Yunque.

Aruba has long been known for its magnificent beaches, and you can check out the unique mixed Dutch/French cultural heritage of St. Maarten. Or Sint Martin. Whichever one you prefer.

This is where timeshare points programs such as Marriott Vacation Club can really be an advantage, since Marriott points owners can stay in properties such as the legendary Marriott's Frenchman's Cove Resort on St. Thomas.

Same with Wyndham timeshare points owners vacationing at Club Wyndham Elysian Beach Resort or Capital Vacations Club members staying at Bluebeard's Castle.

Exchange companies can provide similar options, so even traditional timeshare weeks owners can exchange into a resort on islands such as Barbados.

Bluebeard's Castle Resort

So, Why Timeshare?

The terrific benefits of a timeshare vacation can be as subtle as an in-unit washer/dryer for handling wet bathing suits and towels. Or balconies overlooking some of the most spectacular sunsets on the planet.

Separate bedrooms give you the privacy you need while living rooms and dining tables give you the space the whole family needs. Kitchens let you prepare healthy meals if that’s your choice, or onsite restaurants in case you want to eat out. Plus, resort amenities and Kid’s Club programs give you the full range of activities.

Where to Stay on a Caribbean Getaway

We have the answers, thanks to our website visitors who tell us through their inquiries and offers to buy timeshares. Below is a list of the popular Caribbean timeshares based on their activity, with the most popular showing at the end of the list.

Divi Village Golf and Beach Resort

This amazing resort on Aruba near Druif Beach has everything you need for a terrific beach-based vacation, along with a high quality 9-hole golf course and all-inclusive on-site amenities.

Aruba Beach Club

Stunning Eagle Beach is the site for this resort, which was the first timeshare resort in Aruba. Renovated suite-style accommodations will keep you comfortable throughout your stay.

Divi Aruba Phoenix Beach Resort 

Located on legendary Palm Beach, you’ll have your choice of watersports, multiple swimming pools, Pure Indulgence Spa and oceanfront dining. Plus, you can enjoy the Bubali Bird Sanctuary with over 80 species of bird life.