They may not be the biggest, or have the most amenities. They may be brand new, they may be centuries old.
But the coolest hotels in the Caribbean are the ones that have that indescribable x-factor; where, no matter how many times you come back, it feels at once fresh and timeless.
Cool can mean so many things; but for these hotels spread across the Caribbean, it’s about a sense of place, a sense of purpose, and a sense of personality.
The ninth annual edition of the Cool List spotlights unique, special, one-of-a-kind hotels across the Caribbean.
They may not be the biggest, or have the most amenities. They may be brand new, they may be centuries old. But the coolest hotels in the Caribbean are the ones that have that indescribable x-factor, the one that keeps you coming back, that can only be explained by actually experiencing it. Cool can mean so many things; but for these hotels spread across the Caribbean, it’s about a sense of place, a sense of purpose, and a sense of personality.
The ninth annual edition of the Cool List spotlights unique, special, one-of-a-kind hotels across the Caribbean.
Rockhouse, Jamaica The essence of Caribbean cool. What’s not to love about this cliffside retreat in Negril? The waterside cottages; the sweeping ocean-view suites; the bold, fantastic Pushcart restaurant; and that endlessly feeling that somehow become part of the landscape, even or a few days. There’s a reason after all, that everyone from the Rolling Stones to Bob himself used to come here back in the day.
Anegada Beach Club, British Virgin Islands A combination of glamping tents perched right above the sand and breezy rooms, this is the British Virgin Islands’ bucket list getaway, a stunning place to stay on an island that remains the BVI’s best-kept secret.
Coral Beach Club, St Maarten This all-villa resort is set on a pristine stretch of Dawn Beach, with some rooms abutting Oyster Pond; it’s sleek and modern, with beautifully-designed units that make you feel like you’re living in your own private resort.
Lovango Resort + Beach Club, USVI Lovango started as a private-island beach club just off the coast of St John; now it’s a full-fledged hotel, with a mix of villas, treehouses and luxury tents, the brainchild of Little Gem Resorts, which operates sought-after hotels in Nantucket and Martha’s Vineyard.
The Landing, Harbour Island, The Bahamas It’s one of the first things you see when you get to the dock in Dunmore Town, and it should be: this historic inn, home to the island’s signature restaurant, is home to 13 rooms, all of which you could easily write a novel in. And then there’s that oh-so-lovely pool…
Les Ilets de la Plage, St Barth Secreted away from the rest of the island on its own corner of St Jean beach is this little gem, a clutch of whitewashed bungalows that exemplifies the spirit of St Barth: barefoot chic, carefree, fun.
Golden Rock Resort, Statia The under-the-radar island of Statia has its first “it” hotel, with the debut of the Golden Rock Resort, a stunning, crisp, full-service resort that’s all about Dutch Caribbean hip, including its terrific flagship eatery, Breeze.
Coulibri Ridge, Dominica The newest hotel in Dominica is, true to the island’s spirit, an eco-hotel, but it’s also one of the most design-forward places in all of the Caribbean, all of it solar powered, with out-of-this-world views of the island’s southwestern coast.
Karibuni, Saint Martin Set in the hills in the Cul-de-Sac neighborhood of Saint Martin is this rustic-cool boutique hotel with vibrant rooms (most of which have plunge pools) and a clever flag system that brings fresh pastries right to your door. But the real reason to come here is the private beach club on nearby Pinel Island.
Peace n Plenty, Great Exuma, The Bahamas It’s two destinations in one: a historic, throwback waterside hotel in the heart of Georgetown; and a private beach club on the jaw-dropping beaches of Stocking Island, just acros the bay. In other words, it’s pretty hard to beat.
Delfins Beach Resort, Bonaire When it first opened in 2018, Delfins brought a new kind of personality to the island; since then, it’s cemented its place as the island’s hottest hotel destination, with its #1 in the Caribbean restaurant (the Brass Boer) its beachfront food truck and a fresh, hip aesthetic across its rooms and villas.
Saba Rock, BVI This storied little private island in the heart of the North Sound is finally back and better than ever, with a brand-new look and nine delightfully colorful rooms. What hasn’t changed? The destination bar and restaurant and the hip kitesurfing vibe.
La Casa de la Playa, Riviera Maya This just-opened Riviera Maya adults-only is a far cry from the large-scale resorts that surround it; here, the emphasis is on the Mexican story: star-powered, chef-driven gastronomy, a world-class spa and even little touches like an on-site chocolatier. Oh, and every room has its own plunge pool.
Admiral’s Inn and Gunpowder Suites, Antigua There are few, if any, more beautiful historical towns in the Caribbean than Nelson’s Dockyard, and right at the core is the Admiral’s Inn, a magnificently cultivated boutique hotel in two parts: one in the main part of the harbour, and another across the bay with a fabulous infinity pool deck.
Graycliff, Nassau, The Bahamas It’s hard to make any list of must-visit hotels in the Caribbean and not include Graycliff, the legendary boutique in the heart of Old Nassau; it’s just that it do so well in so many categories – food, drink, history, chocolate, cigars; and can make you happy in so many different ways.
Caerula Mar Club, Andros, The Bahamas The “Renovation Island” hotel has quickly become one of the jewels of the Out Islands of The Bahamas, with lovely bungalow-style accommodations, a crisp, modern look and a a jolt of buzz to far-off South Andros Island.
Love Hotel, Saint Martin The love is back at this popular boutique, finally revived, still smack-dab in the heart of Grand Case Boulevard, with 11 rooms: six on the ocean, five looking out on the always-bustling street. And yes — you can even take excursions on the hotel’s Love Boat.
The Fred, St Croix The hotel that almost single-handedly kick-started the renaissance of Frederiksted is a world on a single block that somehow marries historic charm, South Beach energy and Key West funk, with brilliant service to match.
Rabot Hotel, Saint Lucia Lots of hotels love to talk about experiential travel: here, it’s the real deal: an immersive, thoughtful, creative hotel on a working cacao farm, home to one of the most spectacular pool decks in all of the Caribbean.
Palacio Provincial, Puerto Rico San Juan doesn’t lack for unique places to stay: but its newest entrant, Palacio Provincial, ups the bar; set in a 19th-century diplomatic building in the heart of Old San Juan, with a rooftop pool, a library, revolving nightly cocktail hours and even custom in-room scents.