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Bright, airy living room with white walls and wooden furniture, inspired by Caribbean houses, featuring large windows with stunning ocean views, modern art, decorative plants, and a telescope aimed toward the sea.

6 Surreal Caribbean Vacation Homes

A bright, airy veranda inspired by Caribbean houses, with white walls and ceiling, rustic wooden furniture, a sculpted coffee table, plush seating, potted plants, and open shuttered windows letting in natural light.

Shaken or stirred? Serve guests from the bar at the veranda at the Java Estate, in a listing from Corcoran CA Christie Bahamas.

On the islands of the Caribbean, the water is warm, the palm trees sway, and the rum is flowing — all year round. Dream of a permanent warm-weather escape to one of these idyllic hideaways from across the Corcoran network, including three gorgeous villas on one property on the Bahamas’ iconic Harbour Island, a resort boasting one of the island’s best restaurants in Puerto Rico, a new development in Turks and Caicos, and a unit right on Grand Cayman’s famous Seven Mile Beach.

A covered outdoor dining area with a long wooden table and eight chairs, hanging greenery from the ceiling, stone flooring, and a view of a pool and lush tropical garden—evoking the relaxed elegance of Caribbean houses.

What’s Here: Villa Montaña Beach Resort is a condo hotel set on 32.75 beachfront acres in the Barrio Bajuras of Isabela, Puerto Rico, which has received glowing reviews and awards from both past guests and the likes of Condé Nast Traveler. The sale includes 14 traditional hotel rooms with private terraces and five beach villas that are currently part of the rental program. The sale includes the Eclipse Restaurant (considered one of Puerto Rico’s best), a tennis court, a fitness center, and two pools, as well as an adjacent 8.58-acre beachfront parcel that offers potential for further development.

Why Here: Isabela, on the northwestern coast, is beautiful and low-key — the kind of spot that once you visit, you never want to leave. There are 12 beaches, with options for every kind of beachgoer, whether you’re interested in surfing, swimming, or sunbathing, while nature lovers can hike in the Guajataca State Forest, and joggers and cyclists can enjoy the Paseo Lineal, a 4.5-mile car-free path with smoothie and snack stands along the way.

Listed By: Blanca Hebe Lopez Pierluisi of Corcoran Puerto Rico.

Bright, airy living room with white walls and wooden furniture, inspired by Caribbean houses, featuring large windows with stunning ocean views, modern art, decorative plants, and a telescope aimed toward the sea.

What’s Here: Set high in the hills of coveted Pointe Milou, this property boasts two separate villas. The main villa has two bedroom suites and a living room with three windows on two sides that look out onto a view so staggeringly gorgeous, it seems unreal. A few steps away, there’s a smaller one-bedroom villa. Each villa has its own terrace, outdoor dining area, and swimming pool, allowing for the two properties to be used by two separate parties as income-generating possibilities, or to offer privacy to friends and family when gathering together on this estate. The 7,620-square-meter property gently slopes down to the coast, perching the villas above the sea and Turtle Island.

Why Here: With few restaurants or shops in Pointe Milou, most people drive to nearby Lorient or St. Jean for provisions or to head to the beach. But there is one establishment where people come from all over to visit: Le Ti St. Barth, the island’s go-to nightclub — known near and far for its cabaret dinner shows.

Listed By: Marion Sautereau and Noëlle Carter Dussaule of Corcoran St Barth.

A clear blue swimming pool is surrounded by palm trees, sun loungers, umbrellas, and charming Caribbean houses with porches.

What’s Here: Three individual residences — Java House, Java Cottage, and Java Hut — combine to form the irresistible Java Estate in the heart of Harbour Island. The three homes comprise more than 10,000 square feet of heavenly interior living space, with nine bedrooms and seven bathrooms along the way. Delight in six distinct outdoor spaces, too, including a covered patio with a bar and a poolside pavilion boasting a full kitchen (and a heated pool, of course). A crow’s nest supplies sweeping island vistas, endlessly enchanting at any time of day.

Why Here: Harbour Island, known as “Briland” to locals (say Harbour Island fast and you’ll understand why), is a magical place that’s been the destination of choice for years for those in the know. Located off the northern end of Eleuthera, Harbour Island is known for its New England-style architecture, relaxed and high-end dining and shopping, and a vibe that toes the line between super-chic and wonderfully understated. The residences of Java Estate capture this, contemporary builds that pay homage to traditional Bahamian style.

Listed By: Julian Shaq Gibson and Gavin Christie of Corcoran CA Christie Bahamas.

A modern house inspired by Caribbean houses with large wooden beams and stone accents, featuring an outdoor seating area next to a swimming pool, surrounded by lush greenery and palm trees under a colorful sunset sky.

What’s Here: Cheemaun Beach Villa is the place to get away from it all — a gorgeous three-bedroom, three-bathroom (plus two powder rooms) retreat, covering 3,250 square feet. The great room has soaring vaulted ceilings and floor-to-ceiling glass doors that slide open to reveal a view of the infinity pool and the sea beyond. Feel your shoulders drop immediately when you arrive, and if you need any additional incentives to kick back and relax, just mix up a cocktail from the outdoor wet bar, enjoy your dinner al fresco, and watch the sunset over the perfectly blue waters.

Why Here: Oil Nut Bay is a sustainable, master-planned community on Virgin Gorda’s North Sound that offers private residences with resort amenities. There’s the option of dining at on-site restaurants or hiring private chefs, as well as opportunities for snorkeling, diving, SUP, kayaking, and sailing. There’s also a marina, tennis and pickleball courts, and even an animal sanctuary with an emu!

Listed By: Roz Colthart of Corcoran BVI.

A beachfront resort with a central multi-story building and smaller Caribbean houses, surrounded by palm trees, lounge chairs, and umbrellas along a sandy beach with clear turquoise water under a blue sky with scattered clouds.

What’s Here: This Cayman Islands escape sparkles from beside Seven Mile Beach at the prestigious Caribbean Club. The corner residence affords utmost privacy across its open-concept layout, while also enjoying resort-style living and oceanic panoramas. Its gourmet kitchen is fully equipped and can scale up from cooking a casual evening’s meal to preparing a formal feast with ease. Let the hours tick by on the beachfront balcony, perfect for morning coffee, evening cocktails, and anything in between. Discover further ocean views in the primary bedroom, which also provides a spa-like ensuite and a vast walk-in closet.

Why Here: Seven Mile Beach is a tropical idyll without parallel. From the plush sands, there is nothing but clear, warm waters in front of you, with depths of visibility from 60 to 100 feet. Caribbean Club residents enjoy 300 feet of private beach, plus access to an infinity-edge pool, private loungers and cabanas, and a top-of-the-line fitness center. This section of Grand Cayman is near the island’s capital, George Town, meaning restaurants, shopping, and other activities are in abundant supply.

Listed By: Jessi McNeil of Corcoran Cayman Islands.

Modern outdoor patio with cushioned sofas, a fire pit, and lush tropical plants evokes the charm of Caribbean houses. Glass doors open to a bright dining and living area, while palm trees and blue sky are visible in the background.

What’s Here: Glass and stone go together like, well, the Turks and Caicos Islands at this turnkey four-bedroom home in the boutique Villas at Blue Mountain development. An awe-inspiring indoor-outdoor balance defines life here, from a sloping mountainside overlooking the Atlantic’s impossibly blue hues. Voluminous walls of glass frame the infinite horizon and open to a coral stone deck blessed with covered lounge space, an infinity pool and spa, and a sunken fire pit. Residents also enjoy access to a private beach and a terraced grotto ideal for gatherings of any size.

Why Here: Though 40 islands comprise the Turks and Caicos archipelago, only nine are inhabited. This is a feature, not a bug, giving the Caribbean enclave a stupendously secluded feel. The Villas at Blue Mountain takes full advantage of that atmosphere — Villa 10 is one of only 12 homes in the development, perfect for a full-time, vacationing-centric, or investment property — while residing only 15 minutes from top-tier dining and shopping at nearby Grace Bay.

Listed By: Simon Ferrand of Corcoran Turks and Caicos.

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