In many ways, luxury villas are the ultimate Caribbean vacation experience. It’s far beyond — and very different — than spending your time in a resort. A villa means you aren’t just staying on an island — you’re living on an island, and in the best possible way. But not every island offers this kind of luxury villa experience — you have to know where to go and you have to find the right villa management company to help you both plan your trip and manage your experience on the ground, from renting a car to stocking your fridge to ensuring the villa is properly staffed. It’s the latter that truly separates the greatest villa vacations — the top Caribbean villas can include everything from butlers and in-house chefs to on-demand masseuses.
Because when you’re staying in a villa like this, just about everything you can imagine is taken care of. And isn’t that what luxury is all about?
Here are our favorite Caribbean destinations for the ultimate villa experience, with recommendations on the top companies to help you create your dream villa vacation.
St Barth This is just about the pinnacle of the Caribbean villa vacation — while St Barth is small, it is filled with spectacular villas, both in the hills and right on the beach. For the most authentic St Barth villa experiences, try St Barth Properties.
Barbados As one of the top Caribbean islands for luxury, Barbados offers a massive selection of villas, from smaller boutique accommodations to sweeping grand estates. To find your villa in Barbados, try Villas of Distinction.
Jamaica From the wonderful villas at Round Hill to the spacious homes at the Tryall Club to tucked-away mansions in Ocho Rios, Jamaica has an almost unmatched breadth of villa experiences. What sets the island apart is the always impressive staffing — to the point where you can even run a wedding in a villa. We recommend Villas by Linda Smith.
Anguilla Anguilla has a striking collection of megavillas, modern, high-end properties that in many ways raise the bar for the whole Caribbean, and they’re the perfect way to experience an island known for its food and its beaches. Try using Luxury Retreats.
Providenciales One of the most upscale islands in the region boasts a broad range of villa options. The villas here manage to harness the natural beauty of the island, with a special focus on modern design and indoor-outdoor living. Try TC Villas.
Nevis The tiny island of Nevis has, more than many islands, retained its Old Caribbean charm, and that’s why a villa vacation here is so special. For the best combination of luxury accommodations and service, try the range of villa options at the Four Seasons Resort Nevis.
St Martin You begin your day with a breakfast of French pastries and finish it with a bottle of rose. The French side of St. Martin is a laid-back, effortlessly gourmet destination, and a villa is a terrific way to experience that — this is a place that begs to be explored. St. Martin also has a spectrum of price levels that can accommodate many different kinds of travelers. We suggest using RE/MAX.
Martinique This is such a unique destination that it almost begs for a villa. From the culture to the food to the rhum, Martinique is a place to be explored, a place to be lived. It’s the place for perfect seaside villas, like the Villa Ifrevana in Anses d’Arlet, above. We like the relatively new villa company Villa Veo.
St John This island is famous for its natural beauty, and a villa is the only way to stay right in the thick of the national park, which covers three fifths of the island. With its quirky community, it’s also an island whose daily life is fascinating to experience. We recommend McLaughlin Anderson (the leaders for the whole Virgin Islands).
Grand Cayman This is a wonderful island to live on thanks to its mix of highly-developed infrastructure and tropical ambience, and that’s what makes it even better for luxury villas. We like Cayman Villas.
The British Virgin Islands What most people don’t know about the BVI is that it has some of the best luxury villa product in the Caribbean, from tucked-away hillside villas in Tortola to sprawling beachfront luxury villas in Virgin Gorda. BVI Villa Rental
Mustique The most exclusive island in the Caribbean, this haunt of celebrities and British royals has a sought-after collection of ultra luxury villas offering unmatched privacy and elegance. Your best bet is the world-class Wimco Villas.