For fun in the sun, white sands, turquoise tides, lush vegetation, flavorful cuisine, and rich culture, there are few places that tick all the boxes quite like the Caribbean. The holiday hotspot region is also famous for vacation-worthy accommodations. If you’re more drawn to stylish boutique stays than sprawling resorts, we’ve got some stunning options. From dwellings carved into the sides of cliffs to eco-chic treehouses, each of our favorite design-forward boutique hotels in the Caribbean has its own unique character and personality.
5 Stars | Website | Owen Roberts International Airport
52 | 2 swimming pools; Beachfront; Fitness center | 3
Boatswains Beach; Seven Mile Beach; Laguna Del Mar
Set along one of the most deservedly famous stretches of sand in the Caribbean, Palm Heights is a vibrant, design-centric stay. Perhaps you’ve seen images of the sunburst-yellow umbrellas and loungers draped in matching striped towels arranged on Seven Mile Beach? Unlike the many family-focused Grand Cayman properties, this swish hotel takes a more grown-up approach to things. All the suites face the ocean and flaunt contemporary modular furnishings, “detox/retox” minibars, and marble bathrooms appointed with Aesop toiletries. Tillies draws attention for its warm, stylish atmosphere and mouth-watering regional West Indian cuisine.
5 Stars | Website | Hewanorra International Airport
29 | Beachfront; Free WiFi; Outdoor activities | 1
Soufriere Beach; Malgretoute Beach; Tet Paul Nature trail
Built into the side of a cliff on the island of St. Lucia, Jade Mountain shines as one of the most visually striking properties in all of the Caribbean (and that’s saying something). Everything ties back to the beauty of nature at this legendary luxury escape. Accessed by private bridges, guest “sanctuaries” are built without a fourth wall to ensure that nothing takes away from the spellbinding vistas of the UNESCO-listed Pitons that rise from the sparkling sea. The best spot to soak in the sweeping views? Your own personal en-suite infinity pool, adorned with kaleidoscopic tiles that shimmer in the light.
5 Stars | Website | Providenciales International Airport (PLS)
54 | Swimming pool; Full-service spa; Fitness center | 2
Northwest Point National Park; Malcolm’s Road Beach; Kimcha Village Bird Sanctuary
Removed from throngs of tourists who flock to Grace Bay, Amanyara is tucked away on a remote nature reserve and gives off private island hotel vibes in a way that’s extremely high-end and elegant yet relaxed. The open-air architecture beckons travelers to don flowy garments and pose as if on the cover of some design magazine. Pavilions complete with floor-to-ceiling glass doors, free-standing bathtubs, timber decks, and infinity pools are the perfect way to enjoy every second of the warm weather. The entire property almost seems to float above the impossibly turquoise tides.
4 Stars | Website | Terrance B. Lettsome International Airport
20 | Beachfront; Spa; Tea/Coffee Maker in All Rooms | 1
Annaberg Beach; Maho Bay Beach; Maho Bay Beach
It’s hard to imagine anyone setting eyes on Long Bay Beach Resort and not immediately falling head over heels. Because that would require someone to be immune to the magnetism of trade winds, sugar-like sand, crystal-clear waters, and modern seaside sophistication at its finest. Rooms bring a sense of simplicity that’s at once global and decidedly Tortola with a white-washed palette and rattan furnishings. The breezy common areas beckon travelers to kick back with a refreshing cocktail and a good book. Sure, it’s a little cliche to call something a postcard come to life but when the flip-flop fits…
4 Stars | Website | Sangster International Airport
12 | 1 swimming pool; Full-service spa; Free WiFi | 2
Seven Mile Beach; Hedonism II Beach; Hedonism II Beach
Nestled into the dramatic limestone bluffs in the West End of Negril, The Caves Hotel is an upscale, boutique, all-inclusive vacation sanctuary where people go to get away from the stress of daily life, sip rum punch overlooking the cerulean waves, and relish brown sugar body scrubs in spa cabanas. (The adults-only policy means unwinding fully without the threat of toddler meltdown happening nearby.) Individually designed cliffside cottages exude a breezy charm with thatched roofs, vaulted ceilings, and colorful batik print fabrics. Guests can even book a private candle-lit dining experience in the grotto.
5 Stars | Website | Gregorio Luperon Intl. Airport (POP)
50 | 1 swimming pool; Full-service spa; Beachfront | 3
Playa Dorada; Cofresi Beach; Sosua Beach
Instagramability isn’t the reason to book a vacation, but it certainly doesn’t hurt either. The visual appeal of Casa Colonial Beach & Spa, an oceanfront gem and member of Small Luxury Hotels on the less-trammeled northern coast of the Dominican Republic, can’t be oversold. It’s an absolutely beautiful property that delivers big on contemporary design and amenities while still giving guests that intimate boutique ambiance. Suites have balconies and free-standing outdoor tubs. There’s also a jaw-dropping rooftop infinity pool as well as a spa that pampers guests with indigenous honey and royal jelly treatments.
4 Stars | Website | Norman Manley International Airport
7 | Full-service spa; Pet friendly; Bar | 1
Frenchman’s Cove; Long Bay; Rio Grande
Hidden on a hillside amongst towering banyan trees, Kanopi House offers an intimate and secluded eco-chic stay in the rainforest. Treehouse hideaways are constructed with locally sourced, sustainable materials. The furniture and decor is all crafted by Jamaican artisans, which further underscores the deep sense of place. Time both stops and flies by while wandering the leaf-framed pathways and listening to the sounds of birds singing from your private terrace. Also, we’ve seldom seen a dreamier spot to rinse off than the walkout waterfall showers stocked with signature enviro-friendly toiletries.
5 Stars | Website | Hewanorra International Airport
25 | 1 outdoor pool; Free WiFi; Bar | 1
Gros Piton; Anse Chastanet Beach; St Lucia Sulphur Springs
In terms of breathtaking settings, it’s hard to beat Rabot Hotel from Hotel Chocolat, a St. Lucia gem that rises 1,000 feet above the Caribbean Sea and gazes towards the Piton Mountains. It’s a lush, sustainably-minded refuge from the hustle and bustle of daily life with nature-infused design and a down-to-earth vibe. The open-air restaurant, bar, and spa all tie back to the property’s roots as an organic cacao farm. There’s also a black quartz infinity pool. Ensconced by the leafy embrace of the rainforest, luxury guest lodges feature four-poster beds and rainforest showers ornamented with river stones.
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