If diving into your next Caribbean, Costa Rican, or Bermudan vacation includes a desire to experience a destination on a more local level, your first consideration should be your resort choice. Loyalty programs might steer you toward a favorite hotel brand—and earn you coveted reward points—but when planning to chill out in paradise, why not ditch the familiar and opt for something unique?
Staying at a smaller property owned and managed by a family with roots in the community promises not only a more personalized welcome but also insights into island culture. You’ll get insider tips and feel like you’ve gotten to know the destination as a friend rather than a tourist.
Here are 10 hotels and resorts in the Caribbean, Costa Rica, and Bermuda that offer family-owned hospitality.
Boardwalk Boutique Hotel Aruba
Owned since 2011 by sisters Stephanie and Kimberly, who were born in Aruba before moving to Belgium as young children, Boardwalk Boutique Hotel Aruba is a unique oasis that has been expanded and refined with a focus on eco-friendly practices (it has 80 solar panels) since it first opened on a former coconut plantation just off of Palm Beach more than 30 years ago.
Now featuring 46 private casita-style suites decorated in island-inspired pastel hues, two pools (one with over-water hammocks), an outdoor yoga deck, beach huts with sunbeds just a three-minute walk away on Palm Beach, and healthy vegetarian and vegan breakfast and lunch options at Eduardo’s Beach Shack, the property is perfect for travelers looking to dine around at night (there are walkable options nearby) and experience the Dutch-Caribbean flavors of Aruba.
Bolongo Bay Beach Resort, St. Thomas
Set along 1,000 feet of golden sand on the southern coast of St. Thomas about 4.5 miles from Charlotte Amalie, Bolongo Bay Beach Resort has been owned and operated by the Doumeng family since the 1970s. The 74-room resort features beachfront, oceanview, and garden rooms decorated with a tropical touch, which can be booked on a room-only or all-inclusive basis.
Complimentary snorkeling, kayaking, and stand-up paddle boarding is available right from the beach and guests can also book Bolongo Bay’s 53-foot custom catamaran, Heavenly Days, for sailing trips to swim with turtles, explore St. John National Park, or enjoy a sunset cruise. The Oasis Restaurant and Pool Bar serves locally inspired menus for breakfast, lunch, and dinner and the property is working to rebuild its famous Iggies Beach Bar and Grill, which has been shuttered since back-to-back hurricanes slammed St. Thomas in September 2017.
Frangipani Beach Resort, Anguilla
Featuring just 19 rooms and suites, including a new four-bedroom villa, Frangipani Beach Resort overlooks Meads Bay on one of Anguilla’s most idyllic beaches, where powder-soft sand is washed by calm aquamarine water and a neat row of fringed palapas provide shade—whether you opt to swim in the ocean or in the beachfront pool. The hotel, owned by the Kircher family and managed by Shannon and Scott Kircher, invites sun-seekers to “come as a guest, leave as a friend.”
It is home to the award-winning Straw Hat restaurant, which serves breakfast, lunch, and dinner (with menu options such as blackened shrimp, mahi mahi, lobster tacos, and goat gyoza dumplings). Activity-wise guests can enjoy complimentary watersports, both motorized (tubing, wakeboarding, and waterskiing) and non-motorized (kayaks, stand-up paddle boards, and Hobie Cats) or book a beach-hopping excursion to tiny Sandy Island for snorkeling and lunch.
It’s also easy to stroll along the sand to one of Meads Bay’s beach bars/restaurants to mingle with locals while enjoying an Anguillan sunset.
Graycliff Hotel and Restaurant, Nassau, Bahamas
Wine aficionados likely know about Graycliff Hotel and Restaurant—its award-winning cellar holds 250,000 bottles—and foodies flock here for excellent Bahamian cuisine. But this historic, family-owned hotel is also a serene and romantic place to spend a few nights right in the middle of downtown Nassau.
That means the beach is a taxi ride away, but the lushly landscaped and hand-painted pool serves as a cool oasis for sipping a cocktail between dips and its 18 rooms and suites are decorated with antique furniture befitting a nearly 300-year-old home. The original mansion was built in 1740 by notorious pirate Captain John Graysmith, first became an inn in 1844, and was purchased by Enrico and Anna Maria Garzaroli in 1973, who with their family have built it into a luxury mecca for lovers of food (including chocolate, with a daily Chocolate and Spirits Pairing), wine (stay on a Friday to enjoy a weekly cheese-paired tasting of eight wines), and cigars (the Garzarolis also founded Graycliff Cigar Company).
Jake’s Hotel, Jamaica
Jamaica is famous for its cookie-cutter all-inclusive resorts, but it also has several smaller hotels that offer a less-filtered view of the island and its culture. One of the most welcoming, eclectic, and feel-good is Jake’s Hotel, located not in Montego Bay or Negril but in Treasure Beach on Jamaica’s South Coast.
Its mix of 49 bohemian-style hotel rooms, cottages, bungalows, and villas—each artistically decorated in bright and uplifting island hues with touches of Morocco and Antoni Gaudi—was the vision of Sally Henzell, who was later joined by her son Jason and daughter Justine. Starting with a restaurant and then a single villa in the early 1990s, they have since created a vacation enclave unlike any other.
As guests strike up new friendships around the saltwater pool and lively bar, the vibe is hip yet easy-going and authentic. Even better, Jake’s supports the surrounding community in many ways, from sourcing ingredients for its three restaurants and bars (Jack Sprat, Jake’s Restaurant and Dougies Bar) from local farmers and fishermen to employing residents and supporting the Breds Treasure Beach Foundation, which fosters community empowerment through education and training.
Montpelier Plantation and Beach, Nevis
Montpelier Plantation and Beach, a luxurious hideaway located 750 feet above the Caribbean amid a former 18th century sugar plantation, is owned and managed by the Hoffman family, who have resided on this small Caribbean island for four generations. There are 19 airy rooms and suites, each with elevated décor that feels more contemporary than historic, and a two-bedroom Tamarind Villa with its own private plunge pool.
A spacious and serene pool overlooks a historic stone windmill and guests who prefer the sand and sea can hop a shuttle to the property’s private beach just six miles away. Equally indulgent is the cuisine in Restaurant 750, where specialties include butternut bisque and pan-seared line-caught wahoo, and Indigo, a more casual poolside eatery. But the ultimate culinary experience is the Mill Privée, an intimate, candle dinner for two inside the 300-year-old windmill.
Ti Kaye Resort and Spa, St. Lucia
What began in 1991 with a land purchase by St. Lucia resident Nick Pinnock, became a dream that he eventually transformed into reality years later when he built and opened Ti Kaye Resort and Spa, a secluded, adults-only boutique resort located cliffside above Anse Cochon on the west coast of St. Lucia.
Designed in traditional cottage style—“ti kaye” means “little cottage” in the local Creole language—the property features 33 oceanview rooms and cottages, some with private plunge pools, designed to face the sunset. Romantic mahogany four-poster beds, large balconies with hammocks and rocking chairs, and private outdoor garden showers provide an unplugged, back-to-nature vibe, but air-conditioning and Wi-Fi are fully 21st century.
There are two restaurants: elegant Kai Manje offering stellar views and locally sourced menus, and more casual Ti Manje on the beach serving lunch and pizza. There’s also a pool and a small Kai Koko Spa, which uses locally sourced ingredients to complement Ti Kaye’s authentic St. Lucia spirit.
Villa Beach Cottages, St. Lucia
Now managed by the founder’s grandson, Colin Hunte, Villa Beach Cottages is the kind of small, independent resort that you might stumble upon by chance—and then be so glad you did. Set along a quiet beachfront on Choc Bay on St. Lucia’s northwest coast, just four miles from Castries and three miles from Rodney Bay, the property features 20 villa suites with island-inspired colonial architecture such as gingerbread gables and jalousie-framed windows, along with fully equipped kitchens (stocked upon request with starter pack or custom grocery lists).
This makes the property perfect for families and ideal for travelers who like to prepare breakfast and lunch themselves and then dine around at dinner time (several restaurants are within walking distance, and many are within a 10-minute drive). There’s a small plunge pool and a heated Jacuzzi and complimentary kayaks and snorkeling gear.
Adventure-lovers can book an array of excursions and sweets lovers shouldn’t miss the “bean-to-bar” chocolate tour to La Dauphine Estate, also owned by the same family.
Hotel Belmar, Costa Rica
Costa Rica isn’t an island, but this popular Central America country attracts tropics-loving travelers who appreciate its wild-at-heart rainforest lapped to the east by the Caribbean and to the west by the Pacific. And set in the middle amid the Monteverde Cloud Forest is Hotel Belmar, a family-run boutique property that mixes upscale sustainability, farm-to-table dining, eco-conscious adventure, and artistic culture—all under the enthusiastic watch of general manager Pedro Belmar.
He grew up at the property, which his parents opened 37 years ago, and now oversees its 26 rooms and suites, which range from terraced Peninsula Rooms to a Penthouse Suite with 270-degree views. There’s no pool, but there are soaking tubs in the rooms that are perfect for Monteverde’s crisp evenings and a natural spring-water swimming pond that guests are welcome to use. Nine acres of cloud forest with resident monkeys and sloths along with SAVIA, the hotel’s new 17-acre nature preserve featuring hiking trails and canopy bridges suspended amid the treetops, supply plenty of active adventure for nature lovers as do daily early morning bird-watching walks.
The hotel also has an onsite microbrewery with regular music events and an Artist Residency program during which artists create works inspired by nature and interact with hotel guests.
The Reefs Resort and Club, Bermuda
Owned for more than 40 years by native Bermudians, the Dodwells—David Dodwell, Sr. purchased the resort in 1981 and his son, David Dodwell, Jr., is currently general manager—The Reefs Resort and Club dates to 1947 and occupies a prime cliff-top perch overlooking a postcard-perfect cove on the island’s South Shore.
Featuring a salmon-hued exterior and a pink-sand beach, the boutique resort offers 62 rooms, suites and cottages (there are also 19 private condos available for rental) and its staff is known for the kind of welcoming hospitality long-associated with this 21-square-mile British overseas territory. Guests can choose to dine at several on-property restaurants, including Aqua Terra for seafood and farm-to-table specialties and Coconuts (open seasonally) for more casual local fare along with tropical cocktails prepared at The Sand Bar.
A photogenic infinity-edge pool and hot tub, complimentary snorkel gear and stand-up paddle boards, two all-weather tennis courts, and a La Serena Spa round out the leisure offerings. And the view? It’s definitely sublime.