Jet Set: A Recap of our Trip to Round Hill in Jamaica

A couple of weeks ago, Fabian and I spent a fabulous, long weekend at Round Hill Hotel and Villas in Jamaica. We tend to vacation in cities and usually try to soak up as much as we can when we travel which is enriching, but also exhausting. For this trip, we were in pursuit of some rest and relaxation. We did not plan a single activity and decided to stay on resort the entire time, which was a first for us. This was hands down, the most relaxing vacation we’ve ever had. We both fell in love with Jamaica and in particular, with the beauty, laidback luxury, and old school glamour fo Round Hill and all of the wonderful people who work there and make it feel like home away from home for its guests.

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, Alfred Hitchcock, Bing Crosby, John F. Kennedy and Jacqueline Kennedy who famously honeymooned in Villa 10– which we were able to tour! It was surreal seeing the same bed that the Kennedys slept in and walking over the same floors they’d walked on since that particular villa has been kept in mostly original condition. “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.

There are stunning vistas everywhere you turn at Round Hill. The landscape is lush and beautiful, the white sand beach features crystal-clear water.

Looking Towards the Beach from the Main House

The Main Reception House

There are beautiful canopies of almond trees all around Round Hill. They are lovely and provide a perfect amount of shade on the beach.

A Pretty Pagoda on the Beach

The Walk between the Main Part of the Resort and the Spa is filled with Lush, Tropical Greenery as well as a Cave 

 The View from the Spa towards the Main Part of the Resort

So Beautiful

Stripes Beckon Guests Towards the Chic Ralph Lauren-Designed Bar


Since we were looking for maximum relaxation, instead of staying in a guest room in the Pineapple House, we opted to rent a small, private villa which is the detached guest house of a larger villa.

Our New Favorite Place

Each of the villas at Round Hill is independently owned and so they each have unique interiors. I was drawn to our little villa for the chic, British colonial vibe made up of white textiles, warm mahogany and caning, and rush rugs. Each room was beautifully and comfortably appointed.

All of the villas at Round Hill are built around the idea of indoor-outdoor living as you can see here between our living room and private pool. Notice the incredible view!

The Master Bedroom in our Villa

The View from the Bed highlights the Pool and the Ocean just Beyond

Our Villa had two full bathrooms which were designed very similarly. The master bathroom was stunning as it was swathed in miles of veiny marble with polished nickel fixtures, and custom mahogany cabinets with caning on the doors.

I love the contrast of the warm, rich woods and the gorgeous marble.

The View from our Pool and Patio

The Outdoor Shower Area

Walking to the beach each day was a treat as we’d walk by our neighbor’s beautiful villas on the way down.

According to Kingsley, the wonderful concierge who has worked at Round Hill for over 40 years. If you visit Round Hill, be sure to take one of Kingsley’s tours of the private villas. It is so fun to see the beautiful gardens, lovely interiors, gorgeous vistas, but above all to hear the stories behind each villa. This one is Pierce Brosnan’s favorite.

This is the main villa to our guest cottage, so you’ll notice that the interiors and finishes are very similar. From what we saw, it is among the most beautiful and luxurious villas at Round Hill.

This villa was also quite beautiful and a bit more modern in style. The tasteful interiors were designed by Meg Braff.

This is one of the most spectacular villas at Round Hill and is Sir Paul McCartney’s favorite place to stay.

I could not recommend staying at Round Hill highly enough! In fact, Fabian and I are already talking about going back and are determined to make it an annual trip because we loved it so much. Thank you to everyone who provided tips and insight about this incredibly special place!

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Tell Me What You Think! leave a comment...

    1. Heather, it was absolutely amazing! I completely understand why everyone who loves it goes as frequently as they can. we are going to make it an annual tradition! Thanks for all of your help and insight prior to our trip!

    1. Thanks, Susan! I wondered about the rugs, but did not ask since each villa is independently owned and everyone uses their own designer. I’ll be sure to ask the next time I am there!

    1. Hi Ned– I am not 100% certain about either as I was not at Round Hill in the 1950s to witness it myself, but there are photos at Round Hill of all these people on property and these stories are part of the history shared by the staff at Round Hill. The Kennedys honeymooned in several places and one of the legs of their trip was in fact spent at Round Hill. JFK returned later on to write his inauguration speech in one of the cottages there.

      1. Incorrect. Sorry. Check with Josef Forstmayr, and use my name. Kennedy’s went to Acapulco, LA and SF on their honeymoon, but not Jamaica. They went to RH in 1955. I have a book coming out in late fall on Jamaica tourism post 1945, and I have researched every high end resort thoroughly.