Inside Ralph Lauren’s Corner of Jamaica, Where Style and Legacy Live by the Sea

There are places that trade in flash, and there are places that don’t need to. Round Hill is the latter. This isn’t a resort that tries to keep up with the moment—it’s a destination that helped define one.

Set on 110 acres of lush hillside just west of Montego Bay, Round Hill wears its legacy lightly. It doesn’t flaunt its past, but it doesn’t hide it either. The jet set knew this place long before it was called that. JFK and Jackie stayed here (we stayed in their magnificent villa and adored it). Grace Kelly visited. Noel Coward wrote letters from one of the villas. And for decades, tastemakers and travelers in the know have quietly returned, drawn by something that can’t be manufactured: authenticity.

The Ralph Lauren rooms ooze tropical elegance

At the heart of it all is the Pineapple House, with rooms designed by co-owner Ralph Lauren with the kind of visual clarity only he could bring. These are not stylized hotel rooms—they’re spaces that feel like home, if home had hand-carved mahogany beds, white linen everywhere, and windows that opened directly onto the Caribbean. The design is deliberate but weightless: cool stone floors, plantation shutters, deep soaking tubs, and framed black-and-white photography from Lauren’s own collection. Each bathroom is its own retreat, with rainfall showers, mosaic tilework, and that subtle mix of tropical and timeless you don’t often find outside a magazine spread.

But Round Hill isn’t just about aesthetics. The pace here is unhurried, steady, grounded. You wake with the sun, sip Blue Mountain coffee on a shaded terrace, and move through the day without friction. Swim in the infinity pool, walk down to the beach, or retreat to the spa.

The feel is unmatched

There’s a formality to Round Hill— afternoontea, the clink of ice in a highball glass—but it’s never stiff. This is elegance without ego. Guests greet one another like regulars at a favorite club. Children run barefoot along the lawns. It’s the kind of place where a fashion executive and a novelist might find themselves talking over daiquiris, both dressed down, both completely at ease.

Part of what makes it all work is that Round Hill has never tried to be everything. The resort doesn’t chase trends or overload the senses. Instead, it leans into the things it does best: peace, privacy, personal connection. The villas—27 in total, privately owned—are spread across the hillside, each one different, each with its own view, its own mood. Some have private pools, others open-air living rooms, but all offer the same feeling: you’re not just visiting, you’ve been invited.

The essence of jet-set glamour

Ralph Lauren still keeps a villa here, and you can feel his influence not just in the decor, but in the way the resort breathes. There’s a sensibility at play: American glamour crossed with Caribbean restraint. The color palette is sun-washed. The attitude is casual but exacting. Everything feels effortless—and yet, nothing is left to chance.

Round Hill endures because it doesn’t rely on nostalgia. Its past is a strength, but its present is what keeps people coming back. This is a place that understands that true luxury has little to do with what’s new and everything to do with how a place makes you feel.

And what you feel here is calm. Not the empty kind, but the real kind—the kind that settles into your chest sometime around your second morning, when the sea is flat, the breeze is light, and you realize the outside world has gone quiet. Not because you’ve turned it off—but because Round Hill has given you something better.

Rooms at Round Hill start at $852 in June, according to Google Hotels. Round Hill is a short drive from Montego Bay’s Sangster International Airport.