What happens when you combine the convenience of resort amenities with the seclusion and space of a vacation home? You get a gold star for organizing the best trip ever. When you’re planning a Caribbean resort vacation for family and need more space (especially if your trip includes extended family), booking larger accommodations offers room for everyone, and gives you all more opportunities for intimate family bonding, from room service mornings to evening swims.
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My favorite resorts with villas in the Caribbean are boutique gems that not only offer generous space and more intimate vibes, but also are committed to introducing the local “flavor” to families in sustainable ways. After combing through an array of smaller, more secluded resorts in Caribbean islands that offer vacation home-style digs, I’ve narrowed down the following eight that are sure to please everyone in your party, whether you’re dreaming up a trip with only your kids or an extended family vacation.
1. Windjammer Landing Villa Beach Resort
St. Lucia
Sugar-white buildings with terracotta roofs cascade down a lush hillside, evoking scenes of a Mediterranean seaside village. Everything else about the Windjammer Landing Villa Beach Resort is authentic St. Lucian, and its villas provide the ideal place for families to rest and rejuvenate after long days of exploring. Available in two-, three- and four-bedroom options—as well as ocean view and beachfront locations—the villas come with kitchens, outdoor spaces and even private pools.
Six shared swimming pools, five restaurants, four bars and non-motorized water sports are only the beginning of what’s covered in the resort’s all-inclusive package. What truly sets apart Windjammer Landing Villa Beach Resort are the kid-centric features that make it one of the best family resorts in Caribbean islands for those with smaller children.
Littles will love catching glimpses of Jacquot the Parrot, the resort’s mascot, during select meal times, in addition to activities such as bedtime storytelling and movie nights on the beach. A dedicated kids’ club opens the doors to even more fun experiences, while an optional turn-down service for youngsters includes warm cookies and milk, a souvenir teddy bear and book-reading by Jacquot himself.
2. Frangipani Beach Resort
Anguilla
Like the small, 16-mile-long island it calls home, Frangipani Beach Resort makes guests feel like family the moment they walk through the doors—a nod to its cozy size and family-owned and operated management style. One 5,000-square-foot villa offers four bedrooms whose configurations can be modified to suit varying groups and needs. Highlights include a private pool with a hot tub and lounging deck, full kitchen, bathtubs and outdoor showers, a second-floor balcony overlooking the water, and exclusive dining and activity perks.
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Frangipani is one of the most intimate island resorts in the Caribbean, but it still takes full advantage of its prime real estate on award-winning Mead’s Bay, with various water sports and rental bikes (both complimentary), an exclusive boat tour that hops around the area’s “hidden” islands and coves, and easy access to experience the culture and majestic nature of one of the Caribbean’s best-kept secrets. The resort’s concierge team also can assist families with local babysitting services.
3. The Somerset on Grace Bay
Turks & Caicos
You won’t find any standard hotel rooms at The Somerset on Grace Bay. With all accommodations ranging from three-bedroom villas to five-bedroom “estates,” this Caribbean-British respite affords one of the best family vacations in the Caribbean for those looking for the ultimate privacy. An outdoor space in the form of a terrace or balcony, soaking tubs and rain showers, king master bedrooms, and gourmet kitchens with wine coolers are standard in every villa.
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While there are no private pools, the resort’s “all villa” design allows it to retain a peaceful atmosphere, where the communal pools are never crowded and the beach is pristinely remote. The dedicated kids’ club offers a wide variety of programming for a resort of this size, and babysitting services are optional. Activities like visiting a secluded island, caving, kiteboarding, deep-sea fishing, snorkeling, and culinary and cultural tours serve up fun for the whole family.
4. Sublime Samana Hotel and Residences
Dominican Republic
Among the island’s family resorts, Dominican Republic all-inclusive properties are much more ubiquitous than those with a la carte pricing models. Sublime Samana lies somewhere in between. Families can book various packages that might include staying in one of its accommodations as well as daily breakfast, a spa treatment, an excursion and activities such as a family cooking class or private movie night.
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Sublime Samana is among the most luxurious Caribbean hotels with villas, which are known here as casitas. The casitas come in two- and three-bedroom arrangements are available as either upper- or lower-level units featuring large beds, full kitchens and outdoor spaces with private hot tubs. Beyond their accommodations, families will continue to feel removed from the bustle of one of the Caribbean’s most visited islands, thanks to the resort’s position on the rugged Samana peninsula.
5. Half Moon
Jamaica
Half Moon’s Rose Hall Villas don’t just offer generous space and privacy. The 28 units spanning five, six and seven bedrooms comprise their own “neighborhood,” tucked away from the resort and serviced by its own dedicated team of butlers and personal cooks; nannies are also available upon request. Revered as one of the top luxury Caribbean resorts with private pools, Half Moon ups the ante on how personal outdoor areas can be utilized by offering the ability to host family-style soirees.
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A second “neighborhood” awaits youngsters at the Children’s Village, while unique experiences for the whole family can be had at the resort’s equestrian center as well as through its thoughtfully operated, sea turtle conservation program, and small selection of intimate, cultural tours. Half Moon’s personalized approach and commitment to responsible tourism make it one of the best family resorts Jamaica has to offer.
6. Eden Rock – St Barths
St. Barthelemy
With the largest villas of any resort on this list, Eden Rock– St Barths poises itself to offer the best extended family vacations for larger groups. A plethora of layouts range from one- to four-bedrooms to a whopping five- to 10-bedrooms, all with their own distinct styles and settings. This easily makes Eden Rock the pinnacle of resorts with villas in the Caribbean. Families can build the perfect getaway for their needs, by also choosing from four categories with varying levels of inclusion—the highest coming with butler and personal chef service.
Families will love that all villas include the convenience of daily breakfast, deli meal and snack deliveries as well as beach sets with umbrellas, chairs and cooler boxes making it easier to feed everyone on the go. Reaffirming its position as one of the best family resorts in the Caribbean, Eden Rock upholds the attention to detail for families throughout the property. Kids can join specially curated games and water sports, pottery classes, dance and swimming lessons, yoga, meditation and dedicated spa treatments. Babysitting services are available upon request.
7. Lovango Resort and Beach Club
St. John
Part of the U.S. Virgin Islands, St. John is one of the few Caribbean islands that don’t require a passport from the U.S. This makes it easy to plan a trip with family members who don’t have those little blue books. Reaching Lovango Resort and Beach Club isn’t as simple, but that’s all part of the fun; it’s actually nestled on a private island accessible only by boat, 10 minutes from St. John and St. Thomas.
In line with its super sustainability efforts, the resort offers multi-room treehouse- and glamping-style accommodations in addition to standard villas, making it one of the most unique Caribbean hotels for families. Larger groups can even book the treehouse and glamping villa together—which can comfortably house up to four adults and three kids—as both units are connected by a private boardwalk.
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Family activities are minimal but replete with “wow factor,” and run the gamut from swimming in the resort’s infinity-style pool to hiking trails that are directly accessible from the property or snorkeling, where families can get a first-hand look at Lovango’s coral reef restoration efforts in partnership with the U.S. Virgin Islands. When it comes to dining, the resort goes all out with authentic culinary experiences and themed meals showcasing the local culture and ingredients.
8. Jumby Bay Island Resort
Antigua
All-inclusive resorts with villas can be found throughout the Caribbean, but few cater to families the way Jumby Bay Island Resort does. Beyond the meals, drinks and select activities typically bundled in all-inclusive price tags, the property treats guests to complimentary experiences like round-the-island boat trips, snorkeling and cooking classes — and, for those staying in villas, private water sports and personal service from the kids’ club. Additional highlights of the two-, three- and four-bedroom villas include private pools, full kitchens and personal golf carts.
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Children’s programming puts an emphasis on the outdoors, with organized beach outings; theme parties; consciously guided, turtle conservation excursions; and more. The spa also pampers little ones with manicures and pedicures, as well as massages just for teens. All these offerings collectively make Jumby Bay one of the best family resorts in Caribbean islands for kids of all ages. Want to escape for a romantic day or night out? Drop off your youngsters at the kids’ club, or take advantage of the resort’s babysitting and nannying services.
