Caribbean Connection, From the Bay to the Blue Ridge

A New Way to Own a Caribbean Vacation Home On St. John

By Alexander Britell

St. John has always been one of the most beloved little islands in the Caribbean.

Since the pandemic, it’s become one of the most sought-after destinations in the world, with a growing number of travelers drawn to its stunning natural environment and fun-loving, beachy vibe.

That also means the island’s real estate market is surging, with a limited number of vacation homes available.

But top investment firm Island Sky is changing that, with its new Residence Club: a way for travelers to own in St. John in a unique way, a special opportunity for the island covered by 7,000 acres of National Parkland.

Island Sky St John is an equity residence club in the heart of St John’s Cruz Bay, where buyers can purchase one-tenth ownership in vacation residences starting at $190,000.

The residence club has all of the amenities of a managed resort: with Club hospitality staff attending to every need (and all ownership responsibilities); every residence is fully furnished, with gourmet kitchens and outdoor balconies, along with full access to a spectacular rooftop pool and lounge.

Each residence has just 10 owners, with the benefits of vacation home ownership and the lifestyle of a luxury resort, as Island Sky says.

Owners have equal opportunity to enjoy their Club Residences within their ownership category throughout the year.

“Island Sky is the first and only residence club in St. John,” says Jason Caraway, founder and CEO of Island Sky Investments. “For an owner, this provides the opportunity to enjoy other locations around the world through the Elite Alliance Exchange Program.  Also, as a benefit of the property being fractional ownership, owners enjoy their time and property without the worry of maintenance and the expense of owning the entire property.  Residence members can rest assured the property will be in pristine condition each time they arrive and the staff with be there to attend to all their needs.”


Island Sky St. John is the first in a growing portfolio of projects for the company, starting with an island Caraway fell in love with as a kid.

“I like the small-town feel and carefree attitude,” he tells Caribbean Journal. “The beaches are obviously second to none, but just as important, the people that live in and visit St. John are a big part of what makes it so special. ‘Love City’ has always attracted interesting and adventurous people and it’s a place where I can relate.”

Island Sky has bigger plans to come.

That includes a new Luxury Fractional Real Estate Fund launching later this year, and talks on acquisitions “both stateside and in several Caribbean locations,” Caraway says.

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Publishers Note: We are happy to partner with Alexander Britell, Founder and Editor in Chief of the Miami, Florida based Caribbean Journal and his staff contributing to the OTC and our Caribbean Connection Section. Check out the popular online magazine/website at for valuable information on all fabulous travel options and things of interest in the Caribbean.

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