The historic Round Hill Hotel and Villas opened in 1953 as a playground for the rich and famous. Not a whole lot has changed in the last 60-plus years, but the place is far from antiquated.
This luxury cottage complex boasts 36 hotel rooms designed by Ralph Lauren—with his signature clean lines, fresh white interiors and Jamaican-made materials. The cottages—all 27 of them—are dotted along the expansive property and reflect their own vibe with colorful combinations of Caribbean chic, outfitted with natty bamboo furnishings and private pools.
Down at the main resort, the glittering infinity pool lies just above the blue-green sea where you’ll find guests milling about from one body of water to the next—most with an umbrella beverage of sorts in tow. When they’re not perched on a lounger, nibbling ice-cold fruit kabobs delivered by the staff at just the right moment, you’ll find the more ambitious on kayaks or paddle boards, skimming the warm Caribbean waters.
Just past the beach is the spa, tucked away on 10 acres of lush beachfront lawn in a restored 19th-century plantation house—another nod to the old-world elegance found at Round Hill. The signature hot stone massage uses Jamaican aromatherapy oils to create a therapeutic effect, and frankly, smells intoxicating. It’s here that you’ll find the adults-only pool.
In the evening, cozy couples and families spanning countless generations gather in the cocktail lounge (think Dirty Dancing meets Mad Men) to croon with the piano player while others take a spin on the weathered black-and-white checkered floor. You can easily imagine Fred Astaire, once a visitor of the hotel, doing the same.
Below, Round Hill’s managing director Josef Forstmayr tells us about the most sought-after villa on the property and dishes on the storied past—celebs included.
Most requested room:
What makes it special:
“The six bedroom, six bathroom is the most expensive and most desirable room at Round Hill, making it very popular with celebrities. Recently, Meryl Streep and her family stayed there. It’s very large and therefore perfect for a big family—including Goldie, Kurt and Kate Hudson or the McCartneys, who are often guests, too.”
Your personal favorite room:
“This room is easily accessible but completely hidden. It’s a charming two-bedroom deluxe villa with the original black-and-white checkered floors, an outdoor shower, a lovely pool and original bamboo furniture. It’s near the beach and the action, yet completely secluded.
Lupita Nyong’o, Anna Wintour, Heath Ledger and loads more. Ralph Lauren and Leelee Sobieski who were both spotted (separately, of course) on this journalist’s visit.
Cottage 16 is $3,000-7,200 per night, depending on the season.
“JFK and Jackie came to Round Hill for their honeymoon and visited the resort before they were married (scandalous!). JFK wrote his inauguration speech at Round Hill over Christmas while staying in one of the cottages.”
MORE ROOM REQUEST!