Chic Destination: Round Hill Hotel & Villas in Jamaica

Ever since our trip to Round Hill Hotel & Villas in Montego Bay, Jamaica last year, I have been planning to return! We had an incredible stay. Our time there was super relaxing and the setting could not have been more beautiful. Round Hill is often associated with Ralph Lauren who has two villas on the property and designed the main guest areas. Grace Kelly and Babe Paley also famously retreated to this magical place. It has that special quality which is rather rare– a high degree of style and service in a laidback setting. I also find some of the old-school rules (gentlemen must wear long slacks at dinnertime) to be refreshing in an age where people choose to fly in their pajamas.

Round Hill is steeped in history. The 100-acre peninsula was originally part of Lord Monson’s Round Hill estate– a sugarcane plantation which later grew coconuts and allspice. Eventually, Jamaica-born entrepreneur John Pringle sought to create a boutique hotel concept on the island that would allow for people to purchase villas on the property and share in the hotel’s profits. Famous guests from the Montego Bay resort’s heyday in the 1950s and 1960s include Errol Flynn and Ian Fleming, John F. Kennedy and Jacqueline Kennedy who famously honeymooned in Villa 10, as well as Alfred Hitchcock and Bing Crosby. “The original architecture was designed by William Ballard and the décor was conceived by Guy Roop. Collaborating with Mr. Pringle, they brought to fruition a collection of impeccably designed, freestanding, whitewashed cottages that capitalized on the incredible views of the bay and warm, Caribbean climate.” The cottage colony model that Pringle had devised for Round Hill at 26 years old has since been widely emulated all over the world. For the past sixty years, Round Hill has maintained its relaxed, secluded ambiance and charm, while many of the private villas have been remodeled and modernized. Most recently, the oceanfront rooms in the Pineapple House were redesigned by Ralph Lauren, whose own villa is located at Round Hill, whose influence can be found in his collections every now and again.

I would love to know if you’ve ever stayed at Round Hill and if you would recommend it? We really just want to go somewhere that is a short, direct flight from Houston, where we can relax for say, three days in chic, comfortable surroundings. All I want to do is go to the beach, catch up on my reading, and enjoy what the Italians call “il dolce far niente”, an expression which roughly translates to “the sweetness of doing nothing”. What are your thoughts? Is Round Hill as fabulous as it looks or would you recommend another destination?

{The Pool}

{The Spa at Round Hill}

{The Beach}

{A Tropical Moment}

{One of the 36 Guestrooms in the Pineapple House which were Recently Redesigned by Ralph Lauren}

{A Bathroom in the Pineapple House}

{A Guestroom in the Pineapple House}

{Private Villa No. 7}

{Villa No. 7}

{Villa No. 11}

{Villa No. 16}

{Round Hill is also a Popular Destination for Discerning Brides}

You can read all about our stay at Round Hill last summer in this post and be sure to keep an eye on Instagram as I’ll share glimpses of this stunning locale during our stay.


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  1. paloma – your comment about people flying in their pajamas had me laughing out loud. I couldn’t agree more! bring back the civility! this destination is on our list after your post last year. Enjoy every minute of your trip.