It’s one of the best-kept secrets in the Caribbean: the boutique Round Hill Hotel and Villas in Jamaica, the luxury resort where Ralph Lauren is a part-owner and even designed the hotel rooms. 

But what you may not realize is just how extensive the villa portfolio is: all staffed, all serviced and with a legendary pedigree that includes stays by everyone from Paul Newman to John F. Kennedy (see more from our stay in the JFK-favorite villa). 

Now, the venerable Montego Bay villa resort has added a major new accommodation: Villa 14, set on the historic site of John Pringle, who founded Round Hill. 

The villa is actually a three-villa complex (along with a staff building), anchored by a 4,800-square-foot main house, a tree house and a one-bedroom unit. 

The vision for 14, according to Alexander Wiederin, Creative Director at Buero New York, was to “seamlessly integrate bohemian and campaign styles within a lush jungle backdrop.”

“This was an extraordinary opportunity to help Round Hill create an immersive jungle sanctuary for guests with unique, curated villas and expansive Caribbean views,” said Agatha Habjan, principal at Habjan Studio.

There is everything from private pools for each villa to outdoor showers and even a lap pool and a yoga platform. 

So what does it cost?

Rates start at $4800 per night, including daily breakfast prepared in your villa by the staff. 

— CJ