Luxury Family Vacations in the Caribbean

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, Barbados, St. Barths, St. Martin, Turks and Caicos, or any other idyllic island in the Caribbean, you’re in luck. The region claims more than its fair share of world-class hotels, resorts, and 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. 

What Are The Best Caribbean Islands For A Luxury Family Vacation?

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.

Here’s a look at a few of our favorite spots for family vacations.

St. Barths

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’s concierge team can arrange a babysitter. 

Turks & Caicos

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. 

St. Martin

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. 


A direct flight from many American cities, Barbados offers a perfect combination of convenience and charm. While the beaches offer hours of fun and relaxation, busier little bodies will find action and adventure at attractions like colorful Hunte’s Garden, Barbados Wildlife Reserve, Harrison’s Cave, and its underground tram.

Fancy a swim with local sea turtles against a backdrop of storied shipwrecks? Head to awe-inspiring Carlisle Bay.

Top 7 Luxury Resorts In The Caribbean

1. Rosewood Le Guanahani, Grand Cul de Sac - St. Barths

Overview: Sitting on its own private peninsula, this resort is the perfect destination for solitude seekers. It’s also great for families, thanks to its Rosewood Explorers club. Open to children between the ages of 4 and 11; it offers daily indoor and outdoor activities. These activities also include a taste of local culture thanks to French and English-speaking counselors.

Professional babysitting services are also available through the concierge. 

You’ll Love: The complimentary welcome drink upon arrival, cottage-style rooms with modern amenities, and the on-site children’s playground.

What to Know: If you’re looking for the whole family to be treated like royalty, this newly renovated resort consistently delivers remarkable experiences for guests of all ages. Not feeling up for dinner out? The room service is excellent. 

Insider Tips: Reservations are required in the Rosewood Explorers club, so make sure to book in advance to secure your spots.

Nuts & Bolts: 56 rooms and suites, 10 signature suites (1-3 bedrooms), fitness studio, spa, 2 restaurants; $$$$  

2. Parrot Cay - Turks & Caicos

Overview: This award-winning private island resort offers 1,000 unspoiled acres of unparalleled seclusion. The exceptional service at Parrot Cay is designed to make sure your every want and need is met. There’s also an abundance of activities for kids to enjoy: from the private beach to water sports like kayaking, motor boating, and windsurfing.

Additionally, a dedicated Play by COMO space for kids ages 4-12 is open daily. Babysitting services are also available.

You’ll Love: The daily free full breakfast, free bicycle rentals, game room with pool table, on-site hiking and biking trails, and spacious family-sized villas. 

What to Know: In addition to premier restaurants like Lotus, Terrace, and Como Beach Club, families enjoy Parrot Cay’s themed dining nights featuring live music and creative cuisine. Parrot Cay is also home to the world-renowned COMO Shambhala Spa. 

Insider Tips: A range of accommodations are available for families of all sizes. If you opt for a two-bedroom villa or a larger one, a 24-hour private butler service is available. Don’t want to leave Fido behind? Pets are welcome at Parrot Cay, too. 

Nuts & Bolts: 75 rooms; fitness center, spa, 3 restaurants; $$$$  

3. Sandy Lane - Barbados

Overview: One of the world’s most prestigious resorts, Sandy Lane is celebrated for its outstanding sports facilities, world-class golf, and exquisite spa. Its offerings for families are equally noteworthy, thanks to the Treehouse Club. This vibrant kids’ space is filled with fun activities for kids of all ages. It includes a playground area, daily programs, hourly group swims, and movie viewings. You can also have birthday parties, pool parties, and themed dinner parties for kids. 

The Treehouse Club is also home to The Den, a dedicated space just for teenagers. The Den features a lounge, game room, computer stations, and large-screen televisions. There are also programs for teens, including island tours, water sports, coastal cruises, and more if it's not enough.

You’ll Love: The Gelato Bar; personalized poolside services offering everything from reserved sun loungers to periodic Evian water mistings; and the airport welcome and luxury round-trip transfers. 

What to Know: While Sandy Lane may be best known for its legendary style and prestige, it takes great pride in its family-friendly offerings. 

Insider Tips: In addition to a large gym and training area, daily Pilates, spinning, circuit, and yoga classes are all free. While taxis are always available, you may want to rent a car if you plan on exploring the island.

Nuts & Bolts: 130 guestrooms and suites and a 5-bedroom villa; spa, 4 restaurants, 3 golf courses;  $$$$ 

4. Belmond Cap Juluca - Anguilla

Overview: This exclusive Caribbean hideaway is an ideal place to soak in the sun, have fun, and relax in the Caribbean. Every room has sweeping views, private terraces, and direct beach access—the ultimate convenience for families.

In addition to scheduled supervised children’s activities, Cap Juluca also offers many onsite activities for families, including snorkeling, sailing, island cruises, and kayaking. 

You’ll Love: Luxurious Frette linens; complimentary afternoon tea served “under the dome;” live nightly entertainment. 

What to Know: Traveling with a larger family or group? The multi-bedroom private villas feature their own infinity pools.

Insider Tips: For the most breathtaking views, request a room on the second floor. 

Nuts & Bolts: 69 rooms, 7 patio suites, 6 pool villas; spa, 4 restaurants; $$$$  

5. The Palms Turks & Caicos - Turks & Caicos

Overview: Expect your family’s every need to be meticulously attended to during your stay at this luxury resort on the island of Providenciales. Located on the flawless shores of world-famous Grace Bay Beach, The Palms offers a perfect mix of peace and pampering and adventure and exploration.

Kids are also welcome here, thanks to the Conch Kritters Club, which offers complimentary half- and full-day activities—rain or shine.

You’ll Love: The unbelievable ocean views, the state-of-the-art infinity pool (and swim-up pool bar), and the “mini-village” vibe featuring an assortment of vibrant boutiques, bars, restaurants, and activities.

What to Know: The Palms is slightly removed from the hustle and bustle of other Grace Bay resorts. While this means it’s not as walkable as other resorts, the lack of crowds more than makes up for it. 

Insider Tips: Because of its size, The Palms can be challenging to navigate—especially at night. 

Nuts & Bolts: 72 suites; spa and fitness center; 2 full-service restaurants; $$$$  

6. Belmond La Samanna Resort - St. Martin

Overview: Belmond La Samanna may be known as a mecca for honeymooners, but families aren’t second-class citizens at this luxurious resort. While there isn’t a dedicated kids club, Camp La Samanna offers professional childcare and kids programs, including everything from treasure hunts to water balloon fights. The $100 family rate covers three kids for three hours and includes snacks and drinks.  

You’ll Love: The spacious beach area; complimentary non-motorized watersports like kayaking, paddleboarding, and snorkel gear; and the resort’s resident parrot, Sam. (While sightings are capricious, Sam the Parrot can reportedly be enticed with treats.)

What to Know: Belmond La Samanna has many accommodation options for families, including three-bedroom cottages featuring large outdoor living and dining areas. Additionally, there’s a selection of specialty cottages. Many of these contain convenient mini-fridges, kitchenettes, and sofas. 

Insider Tips: The tropical pathways are illuminated at night, making it easier to navigate them with strollers. While neither the pool nor the beach has on-duty lifeguards, child gates and child alarm bracelets are available upon request.

Nuts & Bolts: 83 rooms and suites, 8 three- and four-bedroom villas; spa, fitness center, 2 restaurants; $$$$

7. Le Barthélemy, Grand Cul de Sac - St. Barths

Overview: This full-scale resort is one of St. Bart’s buzz-worthiest luxury hotels. Featuring stylish contemporary suites and a vibrant social scene, Le Barthelemy is a popular choice for families looking for a true beach resort in a vibrant environment with plenty of action.

Connecting suites are an excellent option for larger families. And pampering here is an equal opportunity experience: Even the spa is kid-friendly.

You’ll Love: The oversized showers and glam Hermès bath products; the tranquil cove views—speckled with kitesurfers—from the serenity of the infinity pool; in-room Nespresso coffee makers; and the all-around youthful vibe.  

What to Know: Different rooms have different allures so take care when booking your lodging. While ground-level ocean suites offer plunge pools, terraces, private gardens, and convenient beach and pool access, they lack privacy, high ceilings, and views of upper-level accommodations.

Insider Tips: Have a family member interested in learning to kitesurf? The well-protected waters of the Grand Cul de Sac lagoon are the perfect place to learn. And the resort’s complimentary kiteboarding, snorkeling, and paddleboarding equipment make it easy to get your watersport on. 

Nuts & Bolts: 44 rooms and 2 suites, fitness studio, spa, 2 restaurants; $$$$  

WIMCO’s resort booking services can help you book your family-friendly Caribbean getaway or answer any questions you may have about luxurious accommodations for families in the Caribbean.

Top 10 Private Villas In The Caribbean As An Alternative To Resort Villas 

Villa Casa Tua (WV CTL) 4 BR - St. Barths

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; $$$$

Villa Kishti West on Meads (AXA KISW) - 5BR - Anguilla

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. $$$$ 

Villa Coral House (PL COR) - 7BR - Turks & Caicos

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; $$$$ 

Villa Windward (AA WIN) 5 BR - Barbados

Overview: This grand villa located in prestigious Sandy Lane Estate offers a consummate combination of glamour and convenience. The main living area opens its gracious French doors to the covered veranda, grand dual staircases, and a well-equipped kitchen. Making Villa Winward an excellent fit for families.

You’ll Love: The immaculately landscaped gardens; and the lotus and koi water feature.

What to Know: As a resident of this villa, you’ll enjoy all the benefits of membership in the Sandy Lane Property Owners’s Association. Including the beach facilities and complimentary beach chairs, umbrellas, washrooms, and showers.

Insider Tips: Situated on a ridge between the third and fifth fairways of premier Sandy Lane Golf Course, Villa Winward is a golfer’s dream.

Nuts & Bolts: 5 bedrooms, 6 baths, pool; $$$$ 

Villa Ela (WV ELA) - 8BR - St. Barths

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; $$$$ 

Villa AWA (PL AWA) - 6BR - Turks & Caicos

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; $$$$ 

Casablanca (BGI CSB) - 5BR  - Barbados

Overview: From beach lovers to shopaholics, there’s truly something for everyone at phenomenal Villa Casablanca. Located in premier Sandy Lane Estate, this 7-bedroom estate is within steps of the beach and close to shopping, restaurants, and more. 

You’ll Love: The well-equipped gym; the ping-pong table, Astroturf tennis, and paddle court; proximity to (and stunning views of) Sandy Lane Golf Course. 

What to Know: As a guest of Villa Casablanca, you’ll have access to everything Sandy Lane has to offer, including the Beach Club and all of its amenities, including private cabanas. 

Insider Tips: Looking for an especially fun (and eco-friendly) way to get around during your stay? A road-licensed, solar-powered golf buggy is available at your request. 

Nuts & Bolts: 7 bedrooms, 7 baths, pool; $$$$ 

Villa Ambiance (SXM AMB) 4 BR  - St. Martin

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; $$$ 

The Beach House (LHE BHS) 8 BR - Anguilla

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; $$$$

Villa Sandyline (PIE SAN) - 6BR - St. Martin

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; $$$$ 

Villa Resort Or Private Villa - Which One to Choose?

If you’ve decided on a family vacation to the Caribbean, you may be deciding between staying at a resort hotel or a private villa resort. There are upsides to both options—the best fit will depend on what you and your family want out of the stay. 

For example, luxury resorts offer a breadth and depth of features and amenities at your fingertips. In addition to upscale accommodations, there are often on-site attractions, including spas, fitness centers, restaurants, bars, and resorts. Additionally, dedicated kids' clubs can make staying at a resort appealing.

Love to socialize and be surrounded by people and activities? A resort hotel may also shine in this area. Finally, there are also resorts with villas for families—which can be a “best of both worlds” solution for some people.

However, private villas have many allures of their own. If privacy is important to you, there’s no substitute for the seclusion you’ll get at private villas. Want to avoid crowds, lines, and waits? A private villa is all yours in every way. 

Private villas may also offer amenities you’d expect exclusively from a luxury resort, such as access to a personal chef, maid service, private swimming pools, in-villa spa services, and more. And WIMCO’s complimentary concierge team is always available to assist you with anything you need.

The takeaway? There is no right or wrong choice. It all depends on your preferences and what an ideal Caribbean vacation looks like to you. 

Why Reserve Your Caribbean Resort Or Villa Via WIMCO? 

When you reserve a Caribbean resort or villa with WIMCO, 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.

Ready To Reserve Your Caribbean Villa Resort Or Private Villa? 

Are you ready to book your stay at one of our family-friendly Caribbean villa resorts or private villas? Or maybe you have a question for one of WIMCO’s villa specialists about which hotel resort or beach 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, Barbados, Turks and Caicos, and Anguilla are especially family-friendly and welcoming for families.

The Caribbean is packed with high-end accommodations, many of which are family-friendly. A few of our favorite Caribbean resorts and villas include Rosewood Le Guanahani, Grand Cul de Sac in St. Barths, Parrot Cay in Turks & Caicos, and Belmond Cap Juluca in Anguilla.