Nestled on a former pineapple plantation along the pristine shores of Jamaica, the Round Hill Hotel and Villas has long captured the hearts of travelers seeking understated luxury and timeless charm. Officially opening its doors in 1953 under the vision of John Pringle, a Jamaican entrepreneur, this iconic resort has since attracted Hollywood royalty and discerning guests from around the globe. Today, Round Hill continues to shine as a beacon of elegance, offering a serene escape steeped in history and sophistication.
Round Hill’s legacy as a retreat for the elite is evident from the moment you step into the Cocktail Bar. Walls adorned with photographs of celebrities such as Pierce Brosnan, Paul McCartney, and designer Ralph Lauren tell the story of a resort that has seamlessly blended Jamaica’s vibrant culture with international allure. Lauren’s influence is particularly visible in the design of the Pineapple House guestrooms, where crisp navy cushions, white furniture, and rich dark wood create an ambiance reminiscent of a classic American country club.
Guests often arrive drawn by nostalgia or the cinematic allure of the resort Villa 11 famously served as a filming location for How Stella Got Her Groove Back. However, what keeps them coming back year after year is the exceptional service and the sense of belonging cultivated by the staff. “We have many repeat guests, some whose parents used to vacation here,” says resort manager Jeremy Zuber. “The history and the dedicated service make Round Hill truly special.”
Spanning 110 lush acres, Round Hill retains its original charm while introducing thoughtful updates to enhance the guest experience. Among its latest additions is Villa 14, a five-bedroom, two-story residence that epitomizes chic Caribbean elegance. Designed collaboratively by Habjan Studio and Buero New York, the villa blends bohemian and campaign styles against a lush jungle backdrop. Guests at Villa 14 enjoy personalized service, including private kitchen staff, a housekeeper, and a gardener, ensuring a bespoke experience.
Other accommodations range from cozy one-bedroom guestrooms to expansive six-bedroom villas, all supported by a responsive villa services team. Whether it’s booking spa appointments, reserving sports courts, or organizing transportation, the team is just a text away, making every stay seamless.
Round Hill offers a blend of relaxation and recreation. For sports enthusiasts, the newly added pickleball courts complement the resort’s well-loved tennis facilities, which now feature professional-led monthly clinics. These sessions provide an opportunity for guests to refine their skills under expert guidance.
Food lovers are equally spoiled, with the resort hosting unique dining events that elevate the culinary experience. During Thanksgiving weekend, I was fortunate to partake in a Michelin-starred dining series led by Chef Marcelo Fukuya. The event showcased an inspired fusion of Jamaican and Japanese flavors, culminating in a magical five-course dinner under the stars. Signature dishes like Kagoshima wagyu and lychee salad left an indelible impression, with Round Hill planning similar events for Easter weekend.
While Jamaica offers countless attractions, Round Hill encourages guests to pause and savor the moment. From reading by the infinity pool overlooking the resort’s private beach to strolling its manicured grounds, the atmosphere invites relaxation. It’s a retreat where the noise of the world fades, replaced by the gentle rhythm of the Caribbean.
With its enduring commitment to quiet luxury, exceptional service, and timeless appeal, Round Hill Hotel and Villas stands as a testament to the transformative power of thoughtful hospitality. For those seeking another side of Jamaica one of elegance, history, and tranquility this iconic resort is the perfect destination.
