12 Awesome Villas For Making Your Caribbean Vacation An Unforgettable Family Affair

Celebrating something big? Catching up for lost time? These tropical resorts have just the right settings.

Whether you're looking to escape for a relaxing week with friends or much-needed fun in the sun with your family, a spacious private villa is an ideal way to connect with those you love as you enjoy the Caribbean. Better yet, what if that villa offered access to resort amenities, such as on-site restaurants, spas and watersports? 

Resort-based villas throughout the Caribbean range from pocketbook-friendly to five-star luxurious and feature amenities many independent, stand-alone villas do not. Here are a dozen top resort-based villa accommodations on eight popular islands.

ACOYA Curacao Resort, Villas and Spa

Conveniently located just 10 minutes from Willemstad's photogenic Queen Emma Bridge but surrounded by lush landscaping and built around a lake, ACOYA Curaçao Resort, Villas and Spa offers upscale seclusion in a relaxed village-like setting with a mix of hotel rooms and spacious one-, two- and three-bedroom villas. 

Each is set amid tropical garden and features a patio, full kitchen and an option to book an all-inclusive package (three meals a day plus snacks). Some villas also have a private plunge pool. On-site amenities at the family-friendly resort include three restaurants, a large pool with dedicated pool bar, a full-service spa and salon, and a water sports and dive center.

Delfins Beach Resort, Bonaire

Bonaire has always been a top dive spot, but with the debut of 13 contemporary luxury villas set on a golden-sand beach, newcomer Delfins Beach Resort offers appealing options for a family or group vacation. Each villa—with either three or four bedrooms, all with their own bathroom—is edged with lush green gardens and palm trees and features a modern kitchen and airy beach-chic décor. Some also have a private pool. 

Villa guests are welcome to enjoy amenities at the resort (which also offers 148 apartments), including an expansive pool, a five-star dive center and the property's al fresco restaurant, Brass Boer, whose owner, Jonnie Boer, is a renowned Michelin-starred chef. 

Coral Beach Club, St. Maarten

The colorful Dutch island of St. Maarten is a convenient spot for a friends getaway or family reunion and Coral Beach Club, located next to its sister property, Oyster Bay Beach Resort, and directly across from the Oyster Pond marina, offers 24 condo-style beachfront villas and townhomes with two-, three- or four-bedrooms—allowing for a budget-friendly stay with plenty of privacy. 

The villas' backyards are steps from white-sand Oyster Beach and it's just a 10-minute drive to the capital, Phillipsburg, where duty-free shopping and eclectic dining await. The villas all have private pools, full-size kitchens (both indoor and outdoor) and complete access to the neighboring Oyster Bay Beach Resort's amenities, which include an infinity pool, spa, fitness center, restaurant and bar.

Villas at Simpson Bay Resort, St. Maarten 

There are 83 condo-style villas set amid the landscaped grounds of St. Maarten's Simpson Bay Resort, Marina & Spa, which also has 272 resort suites. The Villas at Simpson Bay, all renovated in 2020 and accommodating two to six guests in suite and one- or two-bedroom floor plans, offer access to a sheltered private beach and an extensive pool area, creating a tranquil and lush waterfront setting for relaxing and socializing. 

The sprawling Simpson Bay Resort is home to six restaurants, a spa, a fitness center, numerous shops, AquaMania Adventures (a water excursion provider), Thrifty Car Rental, a casino and more. 

Round Hill Hotel and Villas, Jamaica

Welcoming Jamaica-loving sun-seekers since 1953, 110-acre Round Hill Resort and Villas in Montego Bay is known for its 26 private villas, most located on a lushly landscaped hillside overlooking the sea and each featuring its own Caribbean-style design with a blend of retro-romantic and modern elements. Some come with storied histories (JFK and Jackie stayed in Villa 10, Noel Coward and Errol Flynn in Villa 3, and designer Ralph Lauren, who decorated the resort's 36 Pineapple House guestrooms, currently owns a villa here). 

They range from two to six bedrooms (the exclusive Estate Villa can accommodate up to 14 guests), and feature private pools, spectacular views and dedicated staff. Villa guests can enjoy their privacy or the entire atmospheric resort, with amenities that include two restaurants, bars, a spa and infinity pool. 

Private Pool Villas at Cap Juluca, A Belmond Hotel, Anguilla

Set on one of the most photogenic white-sand beaches in the Caribbean, Cap Juluca, A Belmond Hotel, has long lured travelers seeking an escape that combines five-star service and amenities with ultimate privacy. The property's distinctive white Moorish-style architecture is amplified in its villa accommodations, which range from 1,700 to 5,500 square feet and from Beachfront Plunge Pool Two-Bedroom Casitas to Beachfront Three- or Five-Bedroom Pool Villas—all featuring distinctive interior design, spacious indoor-outdoor bathrooms, private kitchens, direct beach access and a 24-hour villa host. 

The resort also has four restaurants, plus private dining options, a spa, tennis courts and watersports.

Villas at Hotel Le Toiny, St. Barth

New at Hotel Le Toiny, the chic hillside boutique hotel on St. Barth, Villa Over the Ocean is a 7,000-square-foot, four-bedroom accommodation that features a 900-square-foot heated pool with an adjacent bar area and gazebo offering splendid views. To be closer to the vivid blue sea, guests can book the unique, four-bedroom Villa Nureyev, constructed in 1970 by the famed Russian dancer with a floating deck surrounded by the ocean. It is located right on the sand near the resort's Beach Club. 

Like guests in the 22 smaller Villa Suites, clustered on a hillside, those staying in both larger villas have access to the property's award-winning restaurant, stunning infinity pool, private beach club, fitness center and spa.

Altamer’s Blue Diamond Villa, Anguilla

Altamer's palatial, 13,000-square-foot Blue Diamond Villa recently celebrated its grand reopening after a renovation that updated its interiors, including the appliances in the chef's kitchen. Up to 11 guests can sleep in the five-bedroom, seven bath villa and enjoy a beachfront pool and hot tub, an entertainment area, movie theater and private fitness center along with 30 pieces of contemporary art. 

While not located within a resort complex, Altamer's five-star amenities include complimentary beer, wine and select spirits, daily continental breakfast, butler service, laundry and turndown, watersports equipment and tennis and basketball courts.

Villas at Palm Island Resort, St. Vincent and the Grenadines

For that private-island experience that truly feels private, Palm Island Resort has two villas located away from the main resort area, each overlooking the sea on either side of the 135-acre island, and a new two-bedroom villa set to open in the spring. Sea Feathers is set right on the sand and features three bedrooms with airy contemporary décor, while Southern Cross is a two-bedroom villa elevated atop scenic cliffs with an infinity pool and access to a nearby beach. 

Both come with a golf cart for easy transport to the resort's beachfront social heart with its restaurant and watersports. Palm Island, which welcomes guests ages 16 and older, is priced on an all-inclusive basis.

Villas at Four Seasons Resort Nevis

Gorgeous golf greens and playful green vervet monkeys are two of the atmospheric perks of a villa stay at the 350-acre, family-friendly Four Seasons Resort Nevis. The property's family-friendly villas all feature private pools and are most are located on the verdant slopes of Nevis Peak while a few are close to the beach. There are two Plunge Pool Studios, each a one-bedroom cottage nestled amid greenery on the lower slopes, and four Sunset Hill Villas with two-to-five bedrooms, located at higher elevations. 

Two Pinney's Beach Villas feature three and four bedrooms and are a short walk from the beach, while eight Palm Grove Villas have two to six bedrooms and are set around the golf course. Four Seasons Resort Nevis also has four showpiece Estate Homes, ranging from 2,905 to 7,025 square feet—the largest sleeps 10 adults and eight children.

Azzurra Castle at Mount Cinnamon Hotel and Beach Club, Grenada

And now for something entirely different. Azzurra Castle at Mount Cinnamon Hotel and Beach Club is easily one of the most unique and charming accommodations you'll find anywhere in the Caribbean. As spacious as it is colorful, it will have guests spending hours after check-in, taking pictures of every nook and cranny, as each room is more fascinating and creative than the next.

At more than 25,000 square feet, guests can get lost in this castle. Up to a dozen friends or family members can stay in the six bedrooms, and they'll enjoy incredible meals from the on-site cook in two dining areas before retiring to the cinema room for movie night or the small beach for fun under the stars.

Villa Diane, Hôtel Barrière Le Carl Gustaf, St. Barth

This newer and extremely popular hotel already sits above Gustavia like a miniature kingdom, and that would make Villa Diane the magnificent castle. This property is already extremely proud of its insanely great views of the island and her surrounding waters, but until a guest has ascended the winding stairs to the top floor's stylish, spacious living area, no one can truly understand just how picture perfect an experience can be in this unparalleled accommodation. 

With five rooms—three of which are suites—this is an ideal situation for the destination wedding of a couple's dreams. As many as 12 guests will sleep and relax comfortably, with the sprawling patios begging everyone to enjoy the St. Barth sun until it sets, which is another beautiful perk. A hidden kitchen is where one of the resort's talented chefs will create amazing meals, all while the party lounges in the cherry on top infinity pool.