The Caribbean of yesteryear—before the clunky beachfront high-rises, jet-choked airports, and comically sized cruise terminals—is not so easy to locate. In most cases, it requires memberships to clubs such as Tryall, Lyford Cay, or Mill Reef, or an invitation to a private home—preferably one that’s been in the family for generations.

The beach at Port Antonio’s cruise pier, near Goblin Hill.

But Goblin Hill, which abuts the idyllic San San Bay, in Jamaica’s Port Antonio parish, is a little bit of both. It’s clubby, as it was originally built as a condominium development by a few couples from Kingston who fancied a weekend escape. And it’s private-ish, as it’s still owned by co-founders Rosalie and Marvin Goodman and frequented by many of the same families.

Fortunately for those who prefer immersion in nature and bottom-shelf rum punch to an infinity pool and tequila concierge, Goblin Hill is open to the public. But, warns Marc Goodman, who now handles development and strategy for his parents’ 28-suite hotel, “there’s no Frette stuff here. It’s a springboard to explore the area—the last quiet, upscale part of Jamaica.”

Rooms that blend outdoors with indoors.

This year, Goblin Hill celebrates its 50th anniversary, and it retains all of its charm. An unapologetic relic of the 1970s, it’s decorated in funky furnishings, wild Italian peacock chairs, and textiles that Warhol and Halston would have loved. “It’s become one of those classic old hotels,” says Goodman with a laugh. “Older people come and wonder why it looks outdated. The younger clientele thinks it’s ironic and cool and hip, and we’re going to embrace that.”

The objective here is to spend as much time outdoors as possible. On that front, Goblin Hill delivers. Occupying two lots on a 700-acre estate, it’s surrounded by a blue lagoon, a 300-foot waterfall, seven beaches, and ample outcroppings to explore on foot.

Green views from anywhere you look.

And then there are the neighbors. Amanda Feilding, the septuagenarian Countess of Wemyss and March (and a renowned researcher and habitué of psychedelics), has a home nearby; the American producer and D.J. Diplo is constructing a large estate.

Pull up a chair.

Meanwhile, at Goblin Hill, very little has changed since it opened, on Easter weekend in 1972. “My parents, through blood, sweat, and tears, have had a good thing going,” says Marc Goodman, who is planning a series of festivities that will run throughout the summer. “There’s a costume shop in Kingston that has hideous 70s clothes,” he says. “Maybe we’ll have a costume party?”

Ashley Baker is a Deputy Editor for Air Mail