Best Caribbean Islands if You Are Traveling with Kids

Traveling with kids to the Caribbean Islands can be pure joy: swimming together, cooking together, playing games in the sun or by sundown… and staying in a villa can make that experience pretty simple. Whether you’re traveling with a little one and looking for a villa on a gentle beach, or pining for a house with all the amenities to keep energized kids happy, we may know just the villa. Looking to get away with the entire extended family? Be sure to take advantage of WIMCO’s Air department, who can arrange all of your flights and connections. Our villa specialists will be delighted to find you a home that fits everyones (big and small!) wants and desires.

Traveling with Young Children…

Villa Les Sables, St. Barths

2 BR, Lorient

WIMCO Villa, Les Sables, WV CHL, St. Barths, Lorient, Family Friendly, 2 Bedrooms, 3 Bathrooms, Pool, WiFi
WV CHL, 2 Bedroom, St. Barths (Lorient)

Have two children under the age of 5? When kids wake up early, you’ll be steps from the gentle water of Lorient beach to build sandcastles and wade in the warm water. Enjoy lunches outside on the large deck, watching the surfers in the distance where the beach breaks.

Villa Sea Dream, St. Barths

1 Bedroom, Marigot

WIMCO Villa Sea Dream, WV DRE, St. Barths, Marigot, Family Friendly, 1 Bedroom, 1 Bathroom, Pool, WiFi
WV DRE, 1 Bedroom, St. Barths (Marigot)

Marigot, a small cove located in between Pointe Milou and Grand Cul de Sac, is a gem of a beach. Truly ideal for small children with its protected corners, the sea here has a different shade of green-blue that you can’t peel your eyes away from. At this one bedroom villa, you’ll have a dock that extends onto Marigot Bay, as well as a private pool.

Villa Sea Breeze, St. Barths

2 Bedroom, Lorient

WIMCO Villa Sea Breeze, WV EZE, St Barths, Lorient, Family Friendly, 2 Bedroom, 2 Bathrooms, Pool, WiFi
WV EZE, 2 Bedroom, St. Barths (Lorient)

At this peaceful two bedroom, bask in a warm breeze from Lorient beach, an ideal spot for young children. Across the road you’ll find a patisserie baking daily croissants and pastries, perfect for cozy breakfasts en famille.

Traveling with Little Adventurers…

Villa Twelve Palms, Turks & Caicos

3 Bedroom, Ocean Point

WIMCO Villa Twin Palms, IE TWE, Turks and Caicos, Ocean Pt/Taylors, Family Friendly, 3 Bedrooms, 3.5 Bathrooms, Pool, WiFi
IE TWE, 3 Bedroom, Turks and Caicos (Ocean Point)

Located on the west side of the island of Providenciales, this Turks and Caicos villa is great for families. With the swim deck in front of the house (kayaks included), plus a tennis court across the street, kids will have a blast staying active.

Villa Sous la Falaise

4 Bedroom, St. Jean Beach

WIMCO Villa Sous la Falaise, HEN SOU, St. Barths, St Jean Beach, Family Friendly, 4 Bedrooms, 4 Bathrooms, Pool, WiFi
HEN SOU, 4 Bedroom, St. Barths (St Jean Baie)

You may just be in the ideal location at this villa. Perched above the quieter section of St. Jean Baie, a private dock allows kids to swim to shore, or snorkel around the villa’s cove. Plus, you’re in walking distance to Village St. Jean with its beaches and restaurants, including the best pizzeria (and family-favorite) Andy’s Hideaway.

Villa La Nina, St. Martin

2 Bedroom, Terres Basses

WIMCO Villa La Nina, C LAN, St. Martin, Hillside/Terres Basses, Family Friendly, 2 Bedrooms, 2.5 Bathrooms, Pool, WiFi
C LAN, 2 Bedroom, St. Martin (Terres Basses)

Have a budding Federer or Sharapova on your hands? This two bedroom villa has its own tennis court and gym. Whether you swim poolside, practice your volleys, or take the 3 minute drive to two nearby beaches, you’ll have plenty to do in St. Martin. (Did we mention it’s a direct flight from New York, too?)

Villa Sol y Sambra, Virgin Gorda

4 Bedroom, Beachside the Baths

WIMCO Villa Sol y Sombra, MAV SOL, Virgin Gorda, British Virgin Islands, Family Friendly, 4 Bedrooms, 4.5 Bathrooms, Pool, WiFi
MAV SOL, 4 Bedroom, Virgin Gorda (The Baths)

If you’re looking for a truly exotic and stunning getaway, but love the idea of a quick flight, think about a family trip to Virgin Gorda. The sand in front of this beachfront property is actually white, and the water unbelievably clear. Take advantage of the amazing snorkeling available in the Baths region, and have fun practicing your strokes at the villa’s lighted tennis court. Night tennis, anyone?


Villa Coyoba, Anguilla

6 Bedroom, Lockrum

WIMCO Villa Coyaba, RIC COY, Anguilla, Lockrum Estates, Family Friendly, 6 Bedrooms, 6.5 Bathrooms, Pool, Wifi
RIC COY, 6 Bedroom, Anguilla (Lockrum)

Anguilla is a great island for extended families traveling together because there are so many large villas. Not to mention that the food is world-class, and the beaches are remarkably clear and picture-perfect. This villa has views of St. Martin, and has a great outdoor area for lunches under the sun.

Villa La Fleur Sur La Mer, St. Barths

5 Bedroom, Colombier

WIMCO Villa La Fleur Sur La Mer, WV BWH, St. Barths, Colombier, Family Friendly, 5 Bedrooms, 5 Bathrooms, Pool, WiFi
WV BWH, 5 Bedroom, St. Barths (Colombier)

With a view over stunning Colombier, this villa is minutes from shopping and dining in town, and lunches and boogie boarding at Flamands beach. You’ll catch amazing sunsets and sunrises here (for the early rises out there). Kids will love hiking down to Colombier and ‘discovering’ its beach, which is only accessible by foot or by boat. At night, teens can see live music in town, or the whole family can snuggle up in this villa’s home theater.

Villa Alila, Barbados

4 Bedroom, Sandy Lane

WIMCO Villa Alila RL ALI, Barbados, Sandy Lane, Family Friendly, 4 Bedrooms, 4 Bathrooms,, Pool, WiFi
RL ALI, 4 Bedroom, Barbados

Barbados is famed for its amazing service, friendliness and hospitality, and so large family groups will truly feel like they’re on vacation here. Villa Alila has beautifully landscaped gardens, and its own private cabana at Sandy Lane Beach.

We’d love to know, what Caribbean island most appeals to your family?