This Iconic Jamaica Resort Is Back Again, With Ralph Lauren-Designed Rooms, Staffed Villas, and Timeless Charm 

One of Jamaica’s most storied hotels is officially back. Round Hill Hotel and Villas has reopened, welcoming guests once again to its private peninsula just west of Montego Bay and marking the return of a property that has long set the standard for charming Caribbean luxury. The reopening brings a full revival of the resort’s accommodations, dining, beach and wellness offerings, restoring a landmark that has shaped Jamaica’s tourism identity for decades.

The announcement was shared with a message that reflected the significance: “The moment we have all been waiting for is finally here: Round Hill Hotel is officially ready to welcome you, our doors are open, and our hearts are full.” It signals not just a reopening, but a return to form for a resort whose appeal has always rested on continuity, discretion and place.

And yes, it really is open — the property even hosted a wedding this past weekend, a sign that it’s firing on all cylinders. 

Set on a secluded stretch of coastline, Round Hill resumes operations with the same low-density layout and emphasis on privacy that have defined the property since its early days. The reopening reinforces Jamaica’s position at the high end of the Caribbean market, where legacy resorts are increasingly valued for their authenticity, heritage and restraint.

The Resort

Round Hill’s accommodations include oceanfront rooms and a collection of private villas spread across the hillside above the bay. While the historic buildings themselves reflect the resort’s original architecture, the interiors of the guest rooms were designed by Ralph Lauren, giving them a residential feel defined by clean lines, crisp palettes and an enduring sense of ease. The focus remains on the setting, with wide views of the Caribbean anchoring nearly every space.

The villas are a defining feature of the resort and have long been part of its allure. Each villa is fully staffed, typically including a cook, housekeeper and gardener, allowing guests to experience a level of privacy and service that feels closer to a private estate than a traditional hotel stay. Many of the villas come with private pools, expansive terraces and sweeping sea views, making them ideal for longer stays and multigenerational travel.

Over the years, these villas have hosted a remarkable list of guests, contributing to Round Hill’s quiet celebrity legacy. Past visitors have included figures such as John F. Kennedy, who famously spent time here before his inauguration, along with writers, musicians and actors drawn to the resort’s discretion and sense of remove. The atmosphere has always favored privacy over spectacle, allowing notable guests to blend seamlessly into the rhythm of the property.

In other words, it’s always about timeless charm, something I feel more deeply every time I stay here.

So how do you choose between the rooms and the villas? Honestly, it’s hard. I will admit that on one trip my family and I actually started in a villa and then extended our trip to stay in one of the rooms for a few days. We loved both.

What We Like

Round Hill’s reopening restores a version of Jamaica that feels increasingly rare. This is a resort defined by proportion and permanence, where space, privacy and service take precedence over trends. The fully staffed villas remain one of the strongest draws, offering a deeply personal experience that works equally well for couples seeking seclusion or families traveling together.

The beach continues to anchor the stay. Sheltered waters, a gently curving shoreline and a setting framed by palms give the property a sense of continuity that regular guests recognize immediately. Dining, spa and wellness offerings round out the experience without overwhelming it, reinforcing the idea that Round Hill succeeds by knowing exactly what it is — and by staying true to it.

How To Get There

Round Hill is located approximately 30 minutes from Sangster International Airport in Montego Bay (which is open and operating again, too). Transfers are straightforward, and the drive along Jamaica’s north coast provides a clear transition from the bustle of town to the resort’s private peninsula.

What It Costs to Stay Here

Rooms are about $1,312 per night right now, according to Google Hotels, in line with what you’d expect for mid-December.