For fun in the sun, white sand, turquoise tides, lush vegetation, tasty cuisine and rich culture, there are few places that tick all the boxes like the Caribbean. The vacation hotspot region is also famous for its vacation-worthy accommodations. If you’re more into stylish boutique stays than sprawling resorts, we’ve got some amazing options. From dwellings carved into the sides of cliffs to eco-chic treehouses, each of our favorite avant-garde boutique hotels in the Caribbean has its own character and personality.
5 stars | Website | Owen Roberts International Airport
52 | 2 swimming pools; Sea side; Fitness Center | 3
Boatswain’s Beach; seven mile beach; Mar Lagoon
Located along one of the most famous stretches of sand in the Caribbean, heights of palm trees is a dynamic and design-focused stay. Have you ever seen images of sun-yellow umbrellas and loungers draped in matching striped towels laid out on Seven Mile Beach? Unlike many family properties on Grand Cayman, this swish hotel takes a more grown-up approach to things. All suites face the ocean and feature contemporary modular furnishings, “detox/retox” minibars, and marble bathrooms stocked with Aesop toiletries. Tillies draws attention for its warm, elegant atmosphere and mouth-watering regional Caribbean cuisine.
5 stars | Website | Hewanorra International Airport
29 | Sea side; Free WIFI; Outdoor activities | 0
Soufrière beach; Malgretoute Beach; Tet Paul nature trail
Built into the side of a cliff on the island of Saint Lucia, jade mountain shines as one of the most visually striking properties in all of the Caribbean (and that’s saying something). It’s all about the beauty of nature in this legendary luxury getaway. Accessed by private bridges, the guest “sanctuaries” are built without a fourth wall to ensure nothing takes away from the spellbinding views of the UNESCO-listed Pitons rising from the shimmering sea. The best place to soak up the stunning views? Your own private 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 Road Beach; Kimcha Village Bird Sanctuary
Far from the tourist crowds that flock to Grace Bay, Amanyara is nestled in a secluded nature reserve and exudes a private island hotel vibe in an extremely upscale and elegant yet relaxed way. The open-air architecture invites travelers to don flowing clothes and pose like on the cover of a design magazine. Pavilions with floor-to-ceiling glass doors, freestanding bathtubs, wooden 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 | Sea side; Spa; Tea/coffee maker in all rooms | 1
Annaberg Beach; Maho Bay Beach; Maho Bay Beach
It’s hard to imagine anyone laying eyes on Long Bay Beach Resort and not immediately fall head over heels. Because it would require someone to be sheltered from the magnetism of the trade winds, sugary sands, crystal clear waters and modern seaside sophistication at its finest. Rooms bring a sense of simplicity that is both global and decidedly Tortola with a whitewashed palette and rattan furnishings. The airy common areas invite travelers to relax with a refreshing cocktail and a good book. Sure, it’s a bit cliché to call something a postcard that comes to life, but when the flip-flop fits…
4 stars | Website | Sangster International Airport
12 | 1 swimming pool; Full-service spa; Free Wi-Fi | 2
seven mile beach; Beach of Hedonism II; Beach of Hedonism II
Nestled in the dramatic limestone cliffs of Negril’s West End, The cave hotel is an upscale, boutique, all-inclusive vacation sanctuary where people go to get away from the stresses of everyday life, sip rum punch with views of cerulean waves, and savor brown sugar body scrubs in cabins in spa. (The adults-only policy means complete relaxation without the threat of collapse from nearby toddlers.) Individually designed cliffside cottages exude airy charm with thatched roofs, vaulted ceilings, and batik-print fabrics colorful. You can even book a private candlelit dining experience in the grotto.
5 stars | Website | Gregorio Luperon International Airport. Airport (POP)
50 | 1 swimming pool; Full-service spa; Waterfront | 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 & Spaa seaside gem and member of Small luxury hotels on the less crowded north coast of the Dominican Republic, cannot be oversold. This is an absolutely stunning property that offers contemporary design and amenities while providing guests with an intimate boutique vibe. The suites have a balcony and a freestanding outdoor bathtub. There’s also a breathtaking 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; Accepted animals ; bar | 1
the cove of the French; long bay; Rio Grande
Hidden on a hill among towering banyan trees, Kanopi House offers an intimate and secluded eco-chic stay in the rainforest. The treehouses are built with locally sourced, sustainable materials. The furnishings and decor are all made by Jamaican artisans, further emphasizing the deep sense of place. Time stands still and flies by as you walk the leaf-lined paths and listen to the birdsong from your private terrace. Plus, we’ve rarely seen a dreamier place to rinse off than the walk-out waterfall showers stocked with eco-friendly toiletries.
5 stars | Website | Hewanorra International Airport
25 | 1 outdoor swimming pool; Free WIFI; bar | 1
Gros Piton; Anse Chastanet Beach; Sulfur Springs of Saint Lucia
In terms of jaw-dropping settings, it’s hard to beat Hotel Rabot of the Chocolate Hotel, a gem of St. Lucia that rises 1,000 feet above the Caribbean Sea and looks toward the Piton Mountains. It’s a lush, eco-friendly retreat from the hustle and bustle of everyday life, with nature-inspired design and a down-to-earth vibe. The restaurant, bar, and open-air spa all tie into the property’s roots as an organic cocoa farm. There is also a black quartz infinity pool. Nestled in the verdant embrace of the rainforest, the luxury lodges feature four-poster beds and rainforest showers adorned with river rocks.
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