Ralph Lauren’s Luxe Jamaican Hideaway

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. Grace Kelly visited. Noel Coward wrote letters from one of the villas. And for decades, tastemakers and travellers in the know have quietly returned, drawn by something that can’t be manufactured: authenticity.

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.

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.

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 colour palette is sun-washed. The attitude is casual but exacting. Everything feels effortless - and yet, nothing is left to chance.