Our 19 Most-Booked Caribbean Resorts

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No. 1. Most Booked Resort in the Caribbean: Cheval Blanc Isle De France, St. Barth’s

A photogenic resort with a loyal following—including of Indagare members—Cheval Blanc Isle De France’s popularity is due in large part to the “alchemists” who go all-out in personalizing the experience for every visiting party from families to couples.

Related: Indagare Index: Caribbean Resorts

2. (Tie) Cap Juluca, A Belmond Hotel & Eden Rock–St Barths

It’s all about location at Belmond Cap Julucain Anguilla, whose Moorish style buildings are spread out across the mile-long private beach. Calm waters make for perfect lazy days soaking in the sun.

And in St. Barth’s, a plethora of water activities, top notch restaurants and programming like modern jazz classes and children’s pastry workshops, make the fabulously scene-y Eden Rock a favorite.

Related: Indagare’s Anguilla Destination Guide & St. Barth’s Destination Guide

4. Four Seasons Resort Anguilla

For a sleek, full-service resort with spacious accommodations, look no further than the family-friendly Four Seasons Resort Anguilla, where glamorous villas come with golf carts and a personal lifestyle assistant.

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5.  (Tie) Rosewood Baha Mar & Sugar Beach, A Viceroy Resort

Rosewood Baha Mar is the most secluded and intimate of the three resorts at Baha Mar in the Bahamas. Expect macarons and Champagne in the hotel’s sophisticated library, a serene palm-lined pool and indulgent spa treatments—plus access to a Jack Nicklaus-designed golf course and other amenities from the 1,000-acre Baha Mar complex.

In St. Lucia, the jungle surroundings of Sugar Beach make it an absolute dream for nature lovers. It’s nestled between the iconic (and Jurassic Park-esque) Piton Mountains, with one of the island’s only white-sand beaches.

Related: Indagare’s Bahamas Destination Guide

7. Rosewood Le Guanahani

One of our picks for Best New Hotels last year, Rosewood Le Guanahani returned with a bang in 2021 following its post-Hurricane Irma rebuild (and rebrand). The classic retreat’s private location and charming cottage-style rooms are a hit with couples and families alike.

8. (Tie) Dorado Beach, a Ritz-Carlton Reserve & Le Sereno

Puerto Rico’sDorado Beach has been a hotspot for celebrities since the 1920s (Amelia Earhart was a frequent flier here), and now its three-mile beach, dreamy spa and stunning water views from every room make it a favorite Caribbean retreat.

A haven for design aficionados, the ultra-contemporary Le Sereno on St. Barth’s was designed by minimalist extraordinaire Christian Liaigre. Its straight lines and stark white and dark wood interiors provide a stunning contrast with the verdant surroundings and placid waters of one of the Caribbean’s calmest beachfronts.

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10. (Tie) Jumby Bay & Amanyara

Located on a private island off the coast of Antigua, Jumby Bay’s laid-back vibe is an undeniable draw, as are the uniquely designed Estate homes and the tradition of traversing the island by golf cart or bike (no cars allowed). Guests here can also participate in wildlife conservation through its Hawksbill Turtle Project.

The sleek infinity pool built from Indonesian volcanic rock is the centerpiece of Amanyara, in the Turks & Caicos, but not even that can overshadow the exquisite service or the stunning villas perched on black rock ledges overlooking the water.

Related: Indagare’s Turks & Caicos Destination Guide

12. Amanera

In the Dominican Republic, Amanera is at once grand and intimate. Its 25 free-standing casitas offer a serene escape with a romantic feel, while plenty of water-based activities keep guests of all ages entertained and the Playa Grand Golf Course (set atop 60-foot coastal cliffs) will have golfers ready to play round after round.

13. (Tie) Rosewood Little Dix Bay; Half Moon, Montego Bay & Four Seasons Ocean Club

With rooms and suites tucked into the lush gardens and villas stowed away on hillsides or by the powdery sand beaches, it is easy to embrace the peaceful barefoot luxury of Rosewood Little Dix Bay, which reopened on Virgin Gorda in the British Virgin Islands under Rosewood in 2020.

Whether you’re looking to relax surrounded by tropical plantings at the Fern Tree Spa or enjoy the multitude of activities (including at a popular equestrian center), Jamaica’s Half Moon offers a great escape from everyday life.

As seen in the 2006 James Bond remake of Casino Royale, the elegant Four Season’s Ocean Club is set on a beautiful stretch of Bahamian beach, and is home to Versailles-like terraced gardens. Indagare members love the three beautiful (though frequently sold-out) beachfront villas.

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16. (Tie) Round Hill Hotel & Villas; Grand Hyatt Baha Mar, Nassau & COMO Parrot Cay

Ralph Lauren-designed, crisp-white resort interiors, formal waterside dinners, and family photos found in some of the villas lend a country club vibe to the blissful Round Hill in Jamaica. Members love its divine (though little) beach.

A veritable wonderland for families and groups of friends, the Grand Hyatt Baha Mar is the largest of the three resorts at the Baha Mar complex. It is home to 1,800 guest rooms, seven swimming pools, a casino, massive entertainment center and a 15-acre waterpark.

The luxury to do nothing is at the core of a stay at COMO Parrot Cay in Turks & Caicos. At this elegant and relaxed property, the ideal experience consists of lounging in one of the free-standing villas (which come with butler service), taking naps on your own stretch of beachfront and (if the spirit moves you) enjoying a complimentary water activity or an ever-popular spa treatment.

19. Sandy Lane

Over-the-top luxury and glamour abound at Sandy Lane in Barbados, where a chauffeured Bentley is available for airport pickups, sheets are embroidered with SL and amenities like the three golf courses and extensive programming for kids and teens await.

Contact Indagare or your Trip Designer for assistance planning your Caribbean getaway at one of these resorts.