Five Surreal 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, from a remote villa on a rocky outcropping to an orbital eco-friendly luxury estate on the cliffs of Virgin Gorda.

Cayman Islands

What’s Here: “Tropical Runaway” is the westernmost estate on Cayman Brac — the last house on the tip of the island — and located on an absolutely perfect stretch of beach. Spread out over 2.5 acres, the property has two houses: The main residence has four bedrooms and three bathrooms, split between two floors, while the smaller cottage is a one-bedroom delight with its own lounge, kitchen, bathroom, and screened porch. There’s a large pool and secluded strip of beach (complete with two fun beach huts with a hammock and deck chairs). The current owners rent out the property when not in residence and both units are in high demand. 

Why Here: Cayman Brac is a half-hour flight from Grand Cayman and an exemplar of laid-back Caribbean life, far from the hustle and bustle of tourist hotspots. Tropical Runaway is known for its access to splendid scuba diving and fishing, but more sedentary pleasures are equally enjoyable here  like enjoying a piña colada and watching the sun set on your private beach.

Represented By: Paul Michael Young of Corcoran Cayman Islands


What’s Here: The Glass Onion of the Bahamas. This one-acre parcel of land runs sea to sea, with 400 feet of beachfront on the north side and a small marina on the south side — a marvelous canvas to fashion your tropical compound. There’s a strategically positioned two-bedroom, three-bathroom villa on a rocky elevation, with sliding doors and windows that take advantage of the site’s unobstructed 360-degree views. Residences here are few and far between, affording true paradisiacal privacy. 

Why Here: Rose Island is just three miles east of Paradise Island but feels much farther, with its unspoiled beaches and a handful of restaurants scattered along its narrow length of 11 miles. There are no roads, and most visitors get to and around the island by boat. You may recognize the island from its appearance in 1965’s Thunderball, when the stolen Vulcan crash lands on its shores.

Represented By: Gavin Christie of Corcoran CA Christie Bahamas.

British Virgin Islands

What’s Here: “Lion Heart” is a magnificent property spanning 12.55 acres with two fully furnished villas designed with rounded flowing lines that stand out in the rocky, yet lush, hills of Oil Nut Bay, set against the backdrop of the Caribbean Sea. Halo, the larger villa, has five bedroom suites, an infinity pool, and an enormous great room. Rainbow, the guest villa, is set slightly downslope, and is an opulent one bedroom, with its own infinity pool, gym, soaking tub, outdoor shower, and spacious great room. The estate was built for David V. Johnson, founder of Oil Nut Bay and broker-owner of Corcoran BVI — exemplifying Johnson’s vision for island life.

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: Live in this ecologically friendly two-story estate set among 25 acres of verdant gardens, right at the edge of El Yunque Rainforest. The property served as a boutique hotel for many years and can continue as such, or can be transformed into a single-family house. The main house has seven spacious bedrooms, each with an en suite bathroom, and a private balcony. There’s also a central courtyard and a kitchen with a wood-fired oven, gas oven, and a curved, polished bar. There’s also separate 1,600-square-foot, two-bedroom, two-bathroom villa that is entirely powered by solar panels and watered by two 800-gallon rainwater cisterns.

Why Here: Fajardo is on the north-eastern shore of Puerto Rico and the hotel is about 15 minutes away from the town center or an hour away from Condado. The property has views of the neighboring islands of Culebra and Vieques, and it’s less than a 20 minute drive to the ferry port, if you want to take a trip to Culebra or Vieques. Fajardo is also home to Las Cabezas de San Juan Nature Reserve, which has Laguna Grande, a bio-luminescent bay popular with nighttime kayakers. 

Represented By: Blanca Hebe Lopez Pierluisi and Alma Martinez Quinones of Corcoran Puerto Rico

St. Barth

What’s Here: This six-bedroom, six-bathroom cliffside estate is named “Villa Good News,” and you’ll definitely find all good vibes here — all the time. The garden has a large pool, an allée bordered by royal palms and flanked by two tiger sculptures, as well as a lush lower terrace with a panoramic view of the Atlantic Ocean. Inside, there’s a home cinema, a roomy home gym, and a Sonos sound system.

Why Here: Grand Cul de Sac is a popular neighborhood in St. Barth, and the eponymous beach and lagoon is a favorite for swimming, snorkeling, and relaxing. Grand Cul de Sac is also a favorite spot for sea turtles, who peacefully paddle alongside you in the calm, shallow waters. For adventures on land, there’s a restaurant for every taste, ranging from casual bars to sophisticated tasting menus.

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

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