Caribbean Confidential: The Islands Where Luxury Feels Like Home

When it comes to Caribbean luxury, the most unforgettable escapes are often the ones that fly under the radar. While the region is known for its dazzling resorts and lively beaches, a more discreet kind of paradise is winning over high-end travelers—those who crave seclusion, space, and elite service that feel more personal.

We spoke to top travel advisors who revealed their favorite islands where luxury lives quietly and beautifully.

Where to Send Upscale Travelers

When luxury clients ask for a Caribbean getaway that is off the beaten path, there are certain islands that stand out as superb choices (and well-kept secrets). They deliver privacy, seamless service, and curated experiences.

“I often suggest Anguilla, St. Barths, or the BVI,” says Wendy Faulenbach, director of leisure travel services, Triad Travel Group LLC, an affiliate of Direct Travel. “These islands are less traveled, boast pristine beaches, and offer either exceptional culinary experiences, personalized water-based activities, or opportunities to relax without large crowds.”

Meredith Rothouse, travel consultant, Edgewood Travel suggests: “I love the villa neighborhoods in Punta Cana between Punta Cana Club and Cap Cana—you get luxury accommodations, great staff, and families love adding a golf cart to check out the various beach clubs or just enjoying their property. Plus there’s the ease and availability of a non-stop flight to Punta Cana when bringing in a multigenerational family from various airports.”

The Villa Option

The villa experience on these quieter islands is quite different, more exclusive, than staying at a high-end resort. Islands like Anguilla and St. Barths have become the go-to for villa-seeking clients who want all the comforts of home, elevated by Caribbean charm and five-star touches.

“Villas offer an amazing way to enjoy the comforts of home while on vacation.” explains Faulenbach. “They often come with their own staff, a private pool, luxurious amenities, and ample beautiful spaces within the villa for families or friends to enjoy. If clients are looking for a full resort experience with spas and gyms, some villas offer these options, or private spa services can be arranged in-house. The quieter islands provide the less crowded, less hectic atmosphere that clients are often looking for to escape.”

Rothouse agrees: “When you are staying at a villa, the experience feels much more intimate and personalized compared to a high-end resort. Now don’t get me wrong, the high-end resorts know our clients’ names, they are repeat guests, they get to know the staff, but not like the one-on-one attention you get with a villa—with your own space, often with stunning views, private pools or beach, and a personal chef that rivals the top restaurants.”

She continues with some specific island recommendations offering villa stays: “On Anguilla and St. Barths, they like the nightlife, the restaurants, but want a place to escape back to that is theirs for some privacy.”

Not Only for the Ultra-Rich

Perhaps surprisingly, luxury private villas are not only for the ultra-rich. They can be positioned as an option for travelers who also need to consider affordability in their trip planning.

“I believe these types of trips cater to the specific desires of a family or client, and there is a price point for all. This is not a product exclusively for the wealthy,” reports Faulenbach. “As you know, many five-star resorts are pricey, and with multiple rooms, it’s often worth investigating villas, which can be similar in cost, yet miles apart in experience.

“The goal is to create a memorable, relaxing, private, and serviced experience that remains within budget. It’s like having friends or family at your home—but here, everyone gets to enjoy a lovely, tailor-made vacation with the amenities of a luxury home in an amazing destination, without the maintenance.”

Rothouse gives a perfect example of a villa stay she booked for a client, where affordability was an important consideration. “Recently, I had a multigenerational group looking at an all-inclusive, multiple rooms at a top All-Inclusive. When I was seeing the cost and knowing the matriarch really wanted everyone in a communal space, and a big enough dining table to fit them all, I knew we would find a perfect spot in Punta Cana in the Punta Cana Club, and we did.

“The daughter said that it was going to be so wonderful to have everyone around a table for dinner, from the kids to the grandkids—and not having to make the meal or clean up! And, it was less than the All-Inclusive! And, out of peak season, typically the minimum night stay may only be four nights, what a great birthday idea or celebration. Once you do it, you keep coming back, especially with the multigenerational families!”

How to Present to Clients

The next step is figuring out how to guide luxury clients toward the more discreet, upscale destinations instead of the usual hotspots, especially with so many Caribbean options to choose from.

“I usually begin by discussing whether clients prefer direct flights or are willing to connect via a ferry or small plane. I also consider what the client hopes to do while on vacation, as these destinations tend to be very private, low-key, and quiet in terms of nightlife,” recommends Faulenbach.

She also incorporates conversations about providing insider extras, such as recommended experiences, local contacts, and/or special perks to elevate the private villa stay for clients.

“Once a client expresses interest, I review options such as included staff, whether for housekeeping, bartending, or a private chef,” notes Faulenbach. “If a chef is not included, we provide pricing and recommend this service for at least a few nights. We also advise on excursions that can be pre-booked, such as water sports, boat charters, and fishing trips. Additionally, we review fast-track options, grocery pre-stocking, and dietary requests. The goal is to personalize the vacation.”

Rothouse approaches clients this way: “If our clients have access to private flights, then we look at the lesser-known islands first, so we can take advantage of harder-to-get-to destinations. And we love showing clients the villas, in any of the Caribbean locations. I think once they can wrap their head around how it works, it typically is the best fit for families.”

She also says that, as a Signature agency, they work exclusively with their villa partners, who have a great concierge product and work directly with them and their clients to find the best experiences during their stay.

The Takeaway

As today’s travelers crave privacy, authenticity, and luxury in equal measure, villas on the Caribbean’s hidden gems offer advisors an irresistible product to promote. These under-the-radar islands promise unforgettable experiences that larger, more crowded destinations simply cannot replicate. By leaning into the exclusivity and bespoke service that villa vacations provide, travel advisors can meet the evolving demands of high-end clients while carving out a lucrative niche.

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