Round Hill Hotel and Villas

"It’s easy to imagine that very little has changed at this 1950s-era resort since John F. Kennedy absconded to Cottage 25 to chip away at his inaugural address and Oscar Hammerstein wrote The Sound of Music while taking in the killer ocean views. The green-striped awnings shading vast terraces and the interiors’ cream-colored paneling offset by dark wood, along with the tea and sandwiches served at four sharp every afternoon, enhance that caught-in-time feeling. That in recent years Ralph Lauren had a major hand in the design is a delightful nonsurprise, with a playful preppiness on display at every turn, like the bar with its deep booth benches upholstered in navy and white stripes and photos of bygone guests, like Warren Beatty, covering the walls. —Charlie Hobbs"

"Up a rocky promontory dense with tropical foliage in Montego Bay, Round Hill Hotel and Villas is a historic Jamaican property that exudes timeless character, elegance, and a strong national identity. The storied estate famously hosted John F. Kennedy and Jackie Kennedy on their honeymoon, John Lennon, Prince Harry and Meghan Markle, and is also home to Ralph Lauren’s two private villas. While the aphorism “if these walls could talk” certainly applies to Round Hill, what if their rackets could talk? The resort enjoys three har-tru and two hard courts, all flanked by dreamy cliffside villas, swaying palm trees, and banana bunches hanging heavy over the courts’ perimeters. The Caribbean seabreeze, soft reggae, and symphony of synchronized frogs make for a glorious surround sound climate, where tennis lessons come with experienced pros and obliging ball boys. Round Hill also hosts an annual tennis tournament for more competitive players, offering guests the chance to play with tennis champions like Bianca Andreescu and Kevin Anderson. Post-game relaxation always follows during daily high tea held in the hotel’s cocktail bar, tastefully designed by Ralph Lauren." - Zachary Schwartz

"Located in Montego Bay, Jamaica, this hotel serves a traditional Jamaican breakfast of ackee and saltfish on the breakfast terrace or poolside in your villa, complemented by fresh-sliced fruit like mango, papaya, and pineapple."

"Stay at the Round Hill Hotel and Villas to get a feel for the island's barefoot luxury." - Travel + Leisure Editors

"Dating all the way back to the 18th century when it operated as a farm, Round Hill opened as a hillside resort in 1953. The 100-acre grounds feature a lovingly restored plantation house, ocean-view villas, suites, and rooms as well as a strip of soft white sand coastline with vibrant coral reefs. In the rooms, interiors have a clean and sophisticated aesthetic for which their designer—and frequent guest—Ralph Lauren is known. This sprawling stay is an ideal option for families, with an array of kid-centric activities, clubs, and dining options, as well as an on-site nanny program. Dining here is also a curated experience, with much of the organic produce grown on the hotel's grounds. Expect fresh Caribbean fare along with great vegan and vegetarian options." - Ruth C. White