The Best Family-Run Caribbean Hotels Have Personal Service, Historic Charm and True Island Roots

You arrive to check in — and the owner is the one handing you the key.
Or maybe they’re walking you to your room. Or setting a place at the dinner table. Maybe it’s their daughter greeting you at breakfast, their son pouring your rum punch. These are the Caribbean’s great family-run resorts — where hospitality isn’t a brand, it’s a way of life.

Across the region, there’s a quiet but deeply rooted network of resorts where the owners live the work. You’ll see them in the kitchens, by the pool, in the garden, walking the beach with guests. Or maybe they’re ensuring that their legacy continues. It’s a style of hospitality that’s rare anywhere else — and it’s what makes these hotels unforgettable.

These are the best family-run hotels in the Caribbean right now.

Bay Gardens Resorts, St Lucia

What began as a single hotel — and a vision by legendary hotelier Joyce Destang — is now a thriving family-run collection — and one of the most successful hospitality brands in St Lucia. Founded and still operated by the Destang family, Bay Gardens includes five distinct properties: the original Bay Gardens Inn, the lively Bay Gardens Hotel, the beachfront Bay Gardens Beach Resort & Spa, the all-suite Bay Gardens Marina Haven, and the luxe Waters Edge Villas. There’s even another one on the way: a luxe, all-villa resort opening later this year. Each one reflects the family’s commitment to community, culture, and value — with warm service, homegrown hospitality, and a genuine connection to the island. Whether you’re traveling solo or with a group, there’s a Bay Gardens for you — and you’re likely to run into a Destang family member while you’re there.

Boardwalk Boutique Hotel — Aruba

Just off Aruba’s Palm Beach, this cheerful oasis is run by Stephanie and Kimberly Rooijakkers — sisters who grew up on the island and now run one of its most charming hotels. Boardwalk blends local authenticity with a modern beachy vibe, full of color and care. The service is thoughtful, the casitas feel like private hideaways, and the sisters’ presence makes it all feel intentional and lovingly maintained.

Graycliff Hotel and Restaurant, Bahamas

Step through the gates of Graycliff and into another era. This iconic Nassau hotel is more than a historic mansion — it’s the vision of the Garzaroli family, who’ve turned it into one of the Caribbean’s most legendary hotels. From the world-class wine cellar to the cigar factory and five-star dining, Graycliff’s old-world grandeur comes with a deeply personal touch. Guests are treated like extended family, with service that’s been honed and perfected over decades.

Spice Island Beach Resort, Grenada

Set along the powdery sands of Grand Anse Beach, Spice Island Beach Resort is one of the Caribbean’s most refined all-inclusives — and still family-run. Founded by the late Sir Royston Hopkin and now lovingly operated by his daughter Janelle, the resort blends polished luxury with warm Grenadian hospitality. Suites open directly onto the beach or private gardens, the cuisine is elevated but rooted in island flavors, and the service reflects decades of family pride. It’s not just a resort — it’s a legacy, where every guest is treated like part of the extended family.

Montpelier Plantation & Beach — Nevis

There’s a timeless quality to Montpelier — the grand mill (where you can actually have dinner), the gardens, the quiet luxury. But the hotel’s modern spirit comes from the Hoffman family, who’ve helped reimagine this centuries-old estate as a warm, welcoming retreat. They’ve kept its soul intact while adding subtle touches of sophistication, from the polished hospitality to the lovely golden lab named Cosmo who’s become part of the guest experience.

Half Moon, Jamaica

Set on 400 acres of beachfront just outside Montego Bay, Half Moon is one of the Caribbean’s most iconic resorts — and it’s still guided by the same family that helped found it in 1954. The Steuart family, one of the original owners, remains deeply involved in the resort’s day-to-day and long-term vision. Chairman Guy T. Steuart III curates the resort’s exceptional legacy.

Despite its scale — with a golf course, equestrian center, award-winning spa, and multiple restaurants — Half Moon retains a sense of intimacy and legacy. That’s the Steuart touch. It’s luxury, yes, but with warmth and authenticity that only comes when a family has shaped a place for generations

Secret Bay, Dominica

Perched on a lush cliffside above the Caribbean Sea, Secret Bay isn’t just Dominica’s most exclusive resort — it’s also a passion project brought to life by husband-and-wife team Gregor and Sandra Nassief. This family-run sanctuary redefines barefoot luxury, with just a handful of secluded villas, each with a private pool, personal attendant, and sweeping ocean views. The service is intuitive, the design is sustainable, and the experience feels like staying at a private home — because in a way, it is. Every detail reflects the Nassiefs’ deep connection to the island, making Secret Bay as soulful as it is spectacular.

Rollezz Villas, Cat Island, The Bahamas

On a remote stretch of Cat Island between Joe Sound Creek and six miles of untouched white sand, Rollezz Villas Beach Resort offers one of the most authentic family-run stays in The Bahamas. The boutique resort features just five duplex villas in colorful Bahamian-colonial style, each with a private veranda and uninterrupted sea views. But what truly sets Rollezz apart are its owners, Yvonne and Carl Rolle, who are ever-present and deeply invested in every guest’s experience.

Frangipani Beach Resort — Anguilla

Right on the sands of Meads Bay, this luxury boutique resort offers more than just spectacular sunsets. It’s a deeply personal project for Scott and Shannon Kircher, who live on site and operate Frangipani as both a hotel and a home. The warmth you feel here isn’t curated — it’s genuine. Guests return year after year for that balance of elegance and ease, where the owners are always around but never in the way.

Bolongo Bay — US Virgin Islands

Since 1974, the Doumeng family has shaped Bolongo Bay into one of the most beloved resorts in the Virgin Islands — and maybe the most fun. This isn’t just a hotel run by a family; it’s a hotel filled with family. Eight Doumengs work on the property, creating an atmosphere that’s friendly, unpretentious, and always buzzing. Whether it’s beachside cocktails, live music, or sailing with staff who feel like old friends, Bolongo is the Caribbean in its purest form.

Cap Maison — St Lucia

Perched above the cliffs near Rodney Bay, Cap Maison is a Mediterranean-Caribbean fantasy brought to life by the Gobat family. From the red-tiled roofs to the signature wine dinners and cliffside Champagne zipline, it’s a place that feels curated by people who love good living. Their hands-on approach and sense of style make Cap Maison one of the most distinctive resorts in the region — refined but never pretentious, home to one of the best restaurants in the whole Caribbean: the Cliff at Cap.

True Blue Bay, Grenada

This vibrant waterfront resort on Grenada’s south coast is owned and operated by the Fielden family, who have shaped it into one of the island’s most beloved boutique escapes. Since 1998, Russ and Magdalena Fielden have led the property with a passion for community, culture, and sustainability. Their daughter Marie also plays an active role in management, continuing the family legacy.

True Blue Bay is as colorful in spirit as it is in design — a place where you might take a morning yoga class overlooking the bay, learn to make chocolate, or share a drink with the owners themselves

Fond Doux — St Lucia

Tucked into the rain-forested foothills of Soufrière, Fond Doux is a working 19th‑century cocoa plantation-turned-eco‑resort, wholly owned and operated by St. Lucian couple Lyton and Eroline Lamontagne. Their vision has transformed the 250‑year‑old estate into a sustainable, artisan‑built retreat that preserves heritage while embracing modern eco‑luxury.