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The Most Stylish Hotels in the Caribbean

Most Stylish Hotels

There are grand hotels and there are beautiful hotels in the Caribbean, small and large, boutique and all-inclusive. But what makes a hotel stylish? It’s that extra attention to detail, that extra emphasis on design and creativity. It’s about seeing a hotel as a piece of artwork in its own right. The Caribbean has no shortage of stylish hotels, places that ooze design flair and inspiration to the point that you feel special just walking inside. These are the Most Stylish Caribbean Hotels.

Most Stylish Hotels

La Suite Villa, Martinique

There’s perhaps no more creatively designed hotel in all of the Caribbean than this boutique in the foothills above Trois-Ilets in Martinique. The brainchild of hotelier Gilles Duplan, everything about this hotel is artful, from the plating of the food at Le Zandoli to the glass floors to the ever-shifting art that sprawls the walls. (And yes, the picture-hanging style is intentional).

Most Stylish Hotels

O:live Boutique Hotel, Puerto Rico

The main inspiration for this hotel was the owners’ honeymoon in the Mediterranean. But it’s so much more than that, from the tassled, color-coded room keys to the outdoor patio fountain soaking tubs. And then there’s the rooftop lounge, which just might be the hippest place in San Juan.

Round Hill

Round Hill, Jamaica

It isn’t easy to make a decades-old hotel stylish, but that’s what’s great about this Jamaican standout: it’s timeless. Of course, it doesn’t hurt that the hotel’s 36 main guestrooms were designed by part-owner Ralph Lauren.

Four Seasons Anguilla

Four Seasons Resort Anguilla

This hotel is opening soon as a rebranded Four Seasons, but it has long been one of the most design-forward hotels in the Caribbean. Its striking lines somehow work perfectly with the beach landscape of Anguilla, and the interior design is inspired, too. Finally, there’s the infinity pool at the Sunset Lounge, one of the most stunning vistas in the whole Caribbean.

Casa Colonial

Casa Colonial, Dominican Republic

In the Dominican Republic’s ocean of all-inclusive resorts, there is a boutique oasis: Casa Colonial in Puerto Plata. This ultra-chic small hotel is the work of Roberto Casoni and his wife, noted designer Sarah Garcia, who have turned the place into a veritable art exhibition.

Carlisle Bay

Carlisle Bay, Antigua

One of Antigua’s most luxurious hotels is also a design stunner, wonderfully executing traditional luxury in a hip, clean, contemporary shell. The best example is probably the hotel’s Library, with a continuously curated collection.

Cooper Island Beach Club

Cooper Island Beach Club, British Virgin Islands

There is something so effortlessly cool about this hotel. The epitome of rustic chic, this is as much an eco-lodge as a private island resort. But the design and vibe here are universally clever, from the delightful Rum Bar to the direction signs.

Ocean View Club

Ocean View Club, Bahamas

This relatively new outpost on Harbour Island has a style that’s at once luxurious and playful, with a decidedly eclectic decor. But like all great stylish hotels, it’s a pastiche of designs that somehow just works. But it also never loses its laid-back, island soul, either.

El Blok

El Blok, Puerto Rico

At first glance, this boutique in Vieques certainly engenders some questions. But that’s the thing about great design — it doesn’t clash with its surroundings — it becomes one with its surroundings. And that’s what this striking hotel, home to a restaurant by celebrity Chef Jose Enrique, has achieved.

JW Marriott

JW Marriott Santo Domingo

A Marriott in a high-rise building above a shopping mall doesn’t immediately make you think “stylish.” But that’s exactly what this hotel is, a modern, energetic hotel that’s among the best executed hotels we’ve ever seen in the Caribbean, from the glass-box rooftop pool to the transparent-floor bar above Winston Churchill Avenue.

Zemi Beach House

Zemi Beach House, Anguilla

Anguilla’s newest boutique hotel immediately brought a new kind of cool to the island, from its minimalist-chic rooms to its spectacularly-designed Taino-inspired Zemi Thai House Spa. Oh, and one of the Caribbean’s most thoughtfully-created rum lists never hurts, either.

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