Five Fabulous Vacation Homes
For Sale in the Caribbean


In 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 five idyllic hideaways from across the Corcoran network, including an award-winning architect’s own abode in Bahamas’ Harbour Island, a collection of sleek glass cottages in Puerto Rico, and a lush retreat on Grand Cayman

Cayman Islands

What’s Here: This Balinese-style retreat in the jungles of Grand Cayman’s North Side has three bedrooms and three bathrooms in the main residence, along with a separate one-bedroom, one-bathroom apartment with its own parking. Live a true indoor-outdoor lifestyle here with doors that open from all parts of the living space to the inner courtyard and the back deck. The primary bedroom has a fully screened patio, while the garden has a large deck, a spacious and deep pool, and an outdoor kitchen. Nature trails wind around the property, including a path to an elevated deck with a hot tub. There’s even an indoor-outdoor shower.

Why Here: North Side is a primarily residential district in Grand Cayman. It’s a place where homes rarely come up for sale, as people who have discovered this side of paradise tend to stay put, enjoying their spacious villas on large and secluded lots. Favorites among the locals include stopping by Starfish Point, with its starfish-filled waters and hiking the Mastic Trail, a centuries-old 2.3-mile path. 

Represented By: Tarah Lawson of Corcoran Cayman Islands


What’s Here: House on a Dune is a spectacular residence built by a noted architect for himself and his family. The two-story structure is set on a sand dune, 33 feet above sea level, and has five bedrooms and five bathrooms. The philosophy behind the house is that the architecture serves a frame for nature and uses elements of the lcoal architectural language — pitched roofs, deep overhangs, and shuttered windows  to create a modern home. The heart of the house is an internal great room or breezeway with sliding doors that open fully to two expansive wooden decks on both sides, with a view of the ocean from one side and tropical forest on the other. 

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 its super chic, yet completely understated vibe. House on a Dune is located on a very private 1.5 acres that has its own path down to the island’s famous pink sand beach. 

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

British Virgin Islands

What’s Here: Unwind in Winedown, a spectacular contemporary two-bedrom, two-and-a-half bathroom villa with sweeping views of Deep Bay and Eustatia Sound. The central living area is flanked by two primary suites, each with its own luxurious bathroom, with both bedrooms and the great room facing the deck, plunge pool, and water views, The line between indoor and outdoor living in almost entirely transparent, thanks to floor-to-ceiling glass doors that showcase the magnificent spectacle of BVI’s sky and sea.
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!

Represented By: Alexander Dobbs of Corcoran BVI.

Puerto Rico

What’s Here: Hacienda ‘La Nube,’ or The Cloud Ranch, is an amazing estate of 53 acres with five separate one-bedroom, one-bathroom 485-square-foot lodges, each with its own balcony, kitchenette, living and dining area, framed with glass walls that overlook the amazing surrounding mountain landscape. There’s also a central atrium, with a state-of-the-art outdoor kitchen and a full bar, as well as an outdoor pool, a fire pit, and numerous open spaces for friends and family to gather together. There are also stables with capacity for 20 horses and a training ring, a water cistern, a full power generator, and parking for more than 20 cars. 

Why Here: Morovis is a hillside town known for La Cabachuelas Natural Reserve, which has more than 60 entry points to a series of caves and caverns, filled with stalactites, stalagmites, and other archeological marvels. Though this secluded estate is tucked away amid the mountains, it’s a short drive to the center of town or just an hour’s drive from the airport in San Juan

Represented By: Blanca Hebe Lopez Pierluisi and Ernesto Santos of Corcoran Puerto Rico

St. Barth

What’s Here: A striking six-bedroom, six-bathroom modern villa offers a perfect mix of private and shared spaces, ideal for multiple families or friend groups to share. The bedroom suites  three suites are on the upper level and another two suites are on the lower level  are designed to serve as almost self-contained cottages. Each suite has a dressing room, bathroom, and private terrace. (There’s a sixth bedroom meant for staff, but can be used as a guest bedroom as well.) There’s a large outdoor terrace, complete with an outdoor kitchen, a very long and heated infinity pool, and inside, a home gym, a lounge, and a sleek kitchen and stylish living room. 

Why Here: Lurin is a mostly residential neighborhood, perched up in the hills, offering stunning views of Gustavia and St. Jean below. It’s also just a short drive from Lurin to Shell Beach or Gouverneur Beach, if you want to relax on the beach or take a swim in the sea. 

Represented By: Guillaume de Corlieu and Marion Sautereau of Corcoran St Barth.

Ready for more?

Get up close and personal with thousands of incredible homes at