Recognized by the 2026 World Travel Awards
Montego Bay landmark also takes Jamaica’s top villa honor as it opens for the 2026-27 season
MONTEGO BAY, Jamaica - Oct. 11, 2026 - Round Hill Hotel & Villas, a private beach enclave of secluded hillside villas and ocean-view rooms and suites, has been named ‘Caribbean’s Leading Villa Resort 2026’ and ‘Jamaica’s Leading Villa Resort 2026’ by World Travel Awards™, recognizing excellence across the travel, tourism, and hospitality industries since 1993. Winners are determined by votes from qualified industry professionals worldwide together with the traveling public.
The dual honor arrives as the iconic Montego Bay resort opens for its 2026-2027 season and marks more than seven decades as the Caribbean’s ‘original private club.’
“John Pringle opened Round Hill in 1953 as a gathering place for an extraordinary circle of friends, which made this the original vetted club long before belonging became something you could purchase,” said Round Hill Managing Director Josef Forstmayr. “Seventy-three years on, the same families return with their grandchildren, and many of our team members carry on work their parents began here. Recognition from our peers across the Caribbean belongs to them.”
That founding circle drew a who’s who of midcentury society, along with the creative figures who shared its sensibility. Grace Kelly found her privacy on the hillside. Cole Porter sang in the bar, Clark Gable and Alfred Hitchcock retreated to the same stretch of coast, and John and Jackie Kennedy spent the early years of their marriage at Round Hill. Princess Margaret learned to waterski in the bay. Celebrity arrived on its own rather than by invitation of a publicist, and the discretion that allowed it remains the operating principle today. Cottage owners, longtime staff, and families now on their fourth generation of Christmases sustain the sense of community that today’s private clubs work to manufacture.
A Season of Gathering
Following a successful inaugural launch this summer, the resort’s exclusive Moët Private Beach returns this winter in partnership with Maison Moët & Chandon. An adults-only stretch of sand beside the spa lawn will entice guests with cushioned double daybeds, signature red and white parasols, and a custom champagne cart pouring Moët & Chandon Ice Impérial, Ice Impérial Rosé, and Impérial Brut by the glass.
Looking ahead into 2027, Round Hill will continue its popular Celebrity Michelin Chef Series across two weekends: James Beard Award winner Chef Rocco DiSpirito over Spring Break, March 17 to 20; and Chef Nello Cassese of the Michelin-starred Ristorante Cipriani at Rio de Janeiro’s Copacabana Palace for Thanksgiving, November 24 to 27. Each weekend pairs an intimate cooking masterclass with a five-course dinner designed by the visiting chef.
Still Time to Book the Festive Season
Limited availability remains for Round Hill’s festive season, themed this year as ‘High Society’ after the Grace Kelly film and the Cole Porter songbook that scored it. Santa arrives by boat on Christmas morning, greeted on the sand by every guest young and old. The tree will be lit at dusk with music and cocktails, candlelit dinners will take over the Seaside Terrace, and the New Year’s Eve Countdown Gala will include a champagne tower, white-gloved canapé service, a live orchestra, Round Hill’s signature Blue Danube Waltz at midnight, and fireworks over the bay. Daily cocktail journeys at the Cocktail Bar, a New Year’s Eve round robin tennis tournament on the clay courts, and programming for younger guests will fill the days between.
For resort reservations or more information, please contact reservations@roundhill.com, call 1-800-972-2159, or visit www.roundhill.com. High-resolution images are available upon request.
About Round Hill Hotel & Villas
Round Hill Hotel & Villas has set the standard for luxury in Montego Bay since 1953, welcoming heads of state, designers, and artists with authentically warm island hospitality. Nestled on 110 verdant acres of former pineapple groves, the resort’s ocean-view rooms and suites are thoughtfully designed and inspired by Ralph Lauren. Guests savor local Jamaican cuisine at the Seaside Terrace restaurant, sip carefully crafted cocktails at three distinctive bar concepts, and dine in-villa for the ultimate in private dining. Offering an idyllic base from which to explore the area, the resort arranges rafting down tropical rivers, ziplining through lush island foliage, and private sunset cruises. Younger guests enjoy a supervised children’s program and on-site nanny services. The Round Hill Spa occupies a restored eighteenth-century house on ten acres above the sea, featuring Elemis aromatherapy products alongside an extensive treatment menu infused with natural and indigenous influences. Five tennis courts, an open-air yoga pavilion, and a fitness center with panoramic floor-to-ceiling ocean views help guests keep to their routines while away. For more information, visit www.roundhill.com.