Shimmering blue waters, sugar-sand beaches, and near-endless sun are just a few of the reasons travelers love the Caribbean. Its breadth and depth of offerings also make it an attractive destination for families.
Whether you’re traveling to Anguilla, St. Barths, St. Martin, or Turks and Caico, you’re in luck. These islands claim more than their fair share of world-class private villa rentals.
Wondering where to start when it comes to deciding where to vacation with kids? You’re in the right place. Read on for our insider’s guide to luxury family vacations in the Caribbean.
The Caribbean is home to more than 7,000 individual islands. (Yes, you read that right.) While they all share some things in common, they also differ in distinct ways ranging from size to offerings. Each Caribbean island also has its own flavor.
While St. Barths may be best known as a haven for the rich and famous, drawn to its exclusivity, it’s also a fantastic destination for families. Gorgeous white-sand beaches, crystal-clear turquoise waters, and the bustling town of Gustavia all offer plenty of fun for families. Love to sail? St. Barths also boasts some of the world’s best sailing conditions.
Despite its glamorous reputation, you’ll find this French-speaking island to be remarkably family-friendly. Babies and children are welcome nearly everywhere. And if you crave an adult night out in the town, WIMCO St. Barth Properties’ concierge team can arrange a babysitter.
Turks & Caicos more than earns its reputation as a romantic getaway. However, it boasts equal allures for families.
Adventure-seekers will find plenty of thrills amidst Turks & Caicos’ beautiful beaches and pristine waters, including world-famous snorkeling, incredible reefs and marine wildlife. And watersports like parasailing, paddleboarding, windsurfing, and more. Many accommodations even include free access to water sports equipment, while others offer convenient jet ski and kayak rentals.
Families will also enjoy exploring the island ruins and plantations, horseback rides, and the weekly Thursday night fish fry at the Bight Settlement on Provo.
Looking to get away from it all with your nearest and dearest? This remote island delivers. While other islands may be more of a “scene,” Anguilla offers an off-the-grid escape for leisure, relaxation, and togetherness.
Warm waters, calm surf, and your pick of kid-friendly accommodations make this tranquil destination an excellent choice for your family vacation.
Home to calm, clear waters perfect for young swimmers, St. Martin may be small in size, but it’s big on culture thanks to a French and a Dutch side. In addition to excellent beaches and accommodations, there’s plenty here for families to see, do, and discover.
A few of our favorite kid-friendly activities in St. Martin? Loterie Farm, the island’s sole private nature reserve; the magical Butterfly Farm; Grand Case village and its quintessential Lolo shacks serving up mouth-watering barbecue; towering Fort Louis; and the thrilling Rhino Safari Excursion.
Overview: This contemporary beachfront sanctuary boasts a plum Lorient location right in front of St. Barth’s hottest surf spot. It offers four spacious bedrooms, an extended pool (with stairs and an alarm), a fully-equipped kitchen with seating for eight, and direct beach access. Making it the perfect escape for families looking for a private retreat.
You’ll Love: Watching the surfers, the dramatic ocean views, and starting every day off with decadent French pastries from Le Petit Colombe—the bakery just across the street.
What to Know: Villa Casa Tua is suitable for families with kids of all ages. In many WIMCO villas, the maid is available to assist with your laundry.
Insider Tips: Want to soak in the island air? The living room window bay fully opens onto the elegant terrace.
Nuts & Bolts: 4 bedrooms and 4 baths; $$$$
Overview: Designed by renowned international Interior Architects Cecconi Simone, this 5-bedroom beach enclave is part of WIMCO’s Private Reserve Collection villas. Meaning your every want and need will be catered to while you are there.
A spacious open-plan great room encompassing the living room, kitchen, and dining areas opens to the terrace and pool for a refreshing and authentic “bringing the outside in” experience.
You’ll Love: The vibrant West End Village location. Restaurants, bars, art galleries, and other attractions are all just steps away. There’s also a home theater and home office—for when recreation or work beckons.
What to Know: Children are anything but an afterthought here. The villa has a huge assortment of beach toys, board games, kayaks, paddleboards, snorkeling equipment (for kids and adults), beach volleyball, a tennis course, and more.
Insider Tips: As a Private Reserve Collection villa, Villa Kishti West includes the unlimited services of a private chef. From drinks and appetizers to gourmet meals. All you have to do? Kick back and enjoy the views.
Speaking of the views, there’s no better location for taking in an unforgettable island sunset than from the furnished rooftop terrace.
Nuts & Bolts: 5 bedrooms and 5 baths, pool, personal chef, concierge, and butler. $$$$
Overview: Villa Coral House, a 12,000 square-foot architectural masterpiece, offers an inimitable combination of refinery and relaxation. It’s mere steps away from the world-famous Grace Bay Beach and within strolling distance of shopping and restaurants.
Part of WIMCO’s Special Reserve Collection, it’s fully staffed for the ultimate in carefree comfort and serenity.
You’ll Love: The separate media room is the perfect place to host family game and movie nights. While the formal dining room overlooking the ocean offers truly stunning daytime and evening views. An outdoor ping pong table will delight both the young and the young at heart.
What to Know: Villa Coral House was recently renovated to new levels of splendor and sophistication. As a Special Reserve Collection Villa, you’ll have access to a private chef and house butlers throughout your stay. You will not have to lift a finger.
Insider Tips: For an authentic taste of island life, gather the family around the outdoor lounge area’s fire pit to watch the awe-inspiring blazing sunset. Traveling with golfers? Coral House is just minutes away from the award-winning Provo Golf Club.
Nuts & Bolts: 7 bedrooms, 7.5 baths, fitness area, pool; $$$$
Overview: Located directly on renowned Flamands Beach, this exquisite private property is just steps away from the golden sand. It’s also within reasonable proximity to everything Cheval Blanc, Baie des Anges, Gustavia, and St-Jean have to offer.
The villa’s eight spacious bedrooms are distributed across several separate bungalows, each of which is its own tranquil retreat.
You’ll Love: The well-equipped modern kitchen, lush covered poolside terrace (for dining and lounging), poolside shower, and playing tennis with the sounds of surf behind you.
What to Know: Need extra shade while lounging by the pool? Villa Ela’s remote-control awnings offer adjustable shade.
Insider Tips: Villa Ela is ideal for gatherings. Plus, we challenge you to find a better sunset view than the one from Villa Ela’s terrace.
Nuts & Bolts: 8 bedrooms, 9 baths, pool, tennis; $$$$
Overview: Enjoy contemporary beachside living at this sophisticated villa in posh Grace Bay. Featuring Europe chic design with island flair, this stunning property boasts direct access to the world-famous Grace Beach. Surround yourself in calming Caribbean hues of white, blue, and verdant green while soaking in tranquil ocean views and breezy trade winds.
You’ll Love: The uber-chic outdoor living space, exquisite infinity pool with built-in sunbeds, and indoor movie room with a high-end sofa and a massive flat-screen TV.
What to Know: Part of WIMCO’s Special Reserve Collection Villa, Villa AWA offers everything you could want or need. This includes unlimited private chef services, house cleaning services, and a high-end security alarm system.
Insider Tips: Don’t worry about gear or equipment. Villa Awa’s got everything from bicycles and kayaks to paddleboards and snorkeling gear. Considering an excursion? WIMCO’s on-island concierge service can organize anything you need.
Nuts & Bolts: 6 bedrooms, 6 baths, pool; $$$$
Overview: Located in lovely Hillside/Terres Basses, this 4-bedroom villa has everything your family needs to enjoy a fantastic getaway in St. Martin. A spacious open-plan living, large outdoor lounge area, well-equipped kitchen are just a few of Villa Ambiance’s outstanding features. The villa also has a large swimming pool with a covered poolside terrace.
You’ll Love: The spectacular sunsets from Villa Ambiance’s hillside perch, the seamless indoor-outdoor flow thanks to its glass walls, spa-like bathrooms, and a large BBQ station.
What to Know: All four of Ambiance’s suites boast king-sized beds, air-conditioning, and ocean views. One suite also has an attached playroom allowing little ones to have their own space.
Insider Tips: Are you planning an extended family trip, wedding, or other gatherings? In addition to being a fantastic family retreat, Ambiance Villa is also an idyllic event venue.
Nuts & Bolts: 4 bedrooms, 4.5 bathrooms, pool; $$$
Overview: If you’re looking for the best of luxurious beach living, you’ll find it—and then some—at this modern and spacious 8-bedroom retreat. Featuring a minimalistic and contemporary design, this bright and airy home is all about relaxation, restoration, and recreation. Plus, it’s just steps from gorgeous Meads Bay Beach.
You’ll Love: The game room; a huge home movie theater that seats up to 16 people (and has its own bar); the upscale gym fitted by Elite Sports Performance; and the gracious welcome platter upon your arrival.
What to Know: Yet another Special Reserve Collection Villa. The Beach House also comes with unlimited access to its own private chef, daily house cleaning services, and a butler.
Insider Tips: Want to keep up your workout regimen? Personal training sessions, yoga, boot camps, and tennis lessons can all be arranged at the Beach House.
Nuts & Bolts: 8 bedrooms, 10.5 baths, pool; $$$$
Overview: Don’t bother trying to decide whether the exterior or interior of this luxury 6-bedroom villa is more impressive; both will take your breath away. Villa Sandyline—located in elite Hillside/Terres Basses—is a wonderland for both the young and young at heart.
From Provencal architecture and inspired Philippe Starck contemporary design to two heated pools, fountains, an infinity Jacuzzi, and more, Villa Sandyline has it all.
You’ll Love: The tropical reef aquarium in the entryway; Two private pools (one with water slide); grand piano; all-weather tennis pavilion; and five magnificent acres of immaculately manicured gardens. And did we happen to mention the fiber optic lit grotto?
What to Know: This property is only available during the Christmas and New Year holidays. There’s also an Art Deco-style private office if remote work calls.
Insider Tips: If you’re looking for an escape from the crowded beach “scene,” Villa Sandyline is a fascinating option.
Nuts & Bolts: 6 bedrooms; 6.5 baths, 2 pools; $$$$
When you reserve a Caribbean resort or villa with WIMCO St. Barth Properties, you get premier concierge service worthy of a five-star hotel. Our friendly staff will handle everything from flight reservations and airport arrivals service to pre-trip arrangements like making restaurant reservations and booking activities.
We bring nearly 40 years of experience and have A LOT of connections on each of these islands. That means you can enjoy absolute peace of mind throughout the vacation planning process.
It’s our business to know everything about luxury travel to the Caribbean. And we genuinely enjoy passing this knowledge and experiences along to you.
Are you ready to book your stay at one of our family-friendly private villas? Or maybe you have a question for one of WIMCO St. Barth Properties’ villa specialists about which villa is the best fit for your family. We’re here to help, so feel free to contact us.
The words “Caribbean” and “luxurious” are practically synonymous. That makes it impossible to narrow it down to one above-and-beyond destination—especially when you factor in their varied allures. But if you’re looking for suggestions, St. Barts, Anguilla and Turks & Caicos tend to be perennial picks on roundups of the region’s most upscale islands.
There’s no clear-cut winner when it comes to the most family-friendly Caribbean resorts and villas. However, many people agree that St Barts, St Martin, Turks and Caicos, and Anguilla are especially family-friendly and welcoming for families.
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