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An ancient image of the beach near Round Hill Hotel & Villas
An ancient image of hotel staff greeting their guests

About Us

Learn More About the History of Our Premier Montego Bay Luxury Resort

A true icon among Montego Bay luxury resorts, Round Hill’s roots are rich with history. Originally, the 100-acre peninsula was part of Lord Monson's Round Hill Estate – a sugarcane plantation that later grew coconuts and pimento (allspice). The peninsular bluff’s fertile soil and ideal climate was also home to pineapple groves, which became forever prominent in the Round Hill logo and can be found sprinkled throughout the property.


An ancient image of a photoshoot at Round Hill Hotel & Villas

Round Hill was conceived by Jamaica-born entrepreneur John Pringle, whose vision was to take the 'boutique' concept both onto another level and into a new domain. John was raised with hospitality in his veins, as his mother owned the former Sunset Lodge Hotel in Montego Bay and was a prominent social figure in Jamaica. After John completed schooling and served in the British Army, he spent a few years in New York City where he worked for Elizabeth Arden and ultimately left to open his own men’s fashion boutique. After meeting his wife and starting a family, John wished to return to Jamaica with his family to put his ambition and talents to work.

An ancient image of three men on a boat at the beach

The plan for our luxury resort in Montego Bay comprised the design and development of a luxury cottage complex that, based on John's revolutionary business model, would offer those who purchased a cottage a share in hotel profits. In other words, he envisioned creating a unique Montego Bay resort that would appeal to the very rich who desired a cottage in the West Indies without the concern of absentee ownership.

John worked tirelessly to turn his dream into reality, and in 1953, Round Hill opened its doors to great acclaim with Sir Noel Coward as its first shareholder. Prominent American and European socialites, literati and artists were invited to build 'cottages' and invest in the hotel. Shareholders included Adele Astaire, Bill and Babe Paley, Lord and Lady Ednam, Mr. and Mrs. Oscar Hammerstein, Clive Brook, Jack and Natasha Wilson, the Marchioness of Dufferin and Ava, Mr. and Mrs. Henry Tiarks and Viscount and Viscountess Rothermere.

An ancient image of the beach near Round Hill Hotel & Villas

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. This 'cottage colony' model that Pringle had devised at 26 years old has since been widely copied by others all over the world.

Over the past sixty years, Round Hill resort in Montego Bay has maintained its secluded ambiance and classic charm while building upon John’s original vision. Many of the cottages today have been fully upgraded and expanded, include modern fixtures and amenities, and boast the latest technology while still maintaining the authenticity that they were built upon. The Spa at Round Hill and surrounding grounds were acquired in 2001, adding 10 additional beachfront acres to the property including a beautifully restored 18th century plantation house.

Today, the inspired capacities of Round Hill’s Managing Director, Josef Forstmayr, and team of highly skilled and dedicated staff have been able to preserve the history and legacy of this iconic resort while staying at the forefront of the current industry.

Take a peek into the wood-panelled bar in Round Hill’s lounge and you will find an array of black and white photographs of times past – depicting the carefree, whimsical and chic, laid-back style that has come to define us as Montego Bay’s most legendary luxury resort.

An ancient image of the beach near Round Hill Hotel & Villas

Our Villa’s Legacy

An ancient image of the beach near Round Hill Hotel & Villas
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Pineapple House

Pineapple House’s 36 deluxe guestrooms were redesigned under the careful direction of Ralph Lauren.

An ancient image of a photoshoot at Round Hill Hotel & Villas
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Villa 3

Sir Noel Coward, Errol Flynn and Ian Fleming were known to holiday in Jamaica quite often.

Viscount Esmond Rothermere ("Daily Mail" newspaper fortune) was the original owner of Cottage 16 at Round Hill with Lady Anne Rothermere, his wife.

In this villa, history tells us that Ian Fleming's 'good friend' Lady Rothermere heated up their relationship until Noel Coward and Ian decided to move down the coast to Orecabessa to start a property similar to Round Hill.

This property was owned by one of their Jamaican friends - Blanche Blackwell. Blanche wanted to develop a similar resort there. Blanche's son, Chris Blackwell, is continuing this dream with the recent opening of Goldeneye in Orecabessa.

Errol Flynn actually bought Navy Island in Port Antonio, another 2 hours’ drive east of Orecabessa. His widow Patrice Wymore-Flynn still operates her cattle farm there

An ancient image of three men on a boat at the beach
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Villa 10

John F. Kennedy and Jackie Kennedy preferred to stay in this four-bedroom villa with pool because of its privacy, magnificent view and large lawn, great for entertaining and children's play. In fact, JFK and Jackie Kennedy honeymooned in this villa.

An ancient image of hotel staff greeting their guests
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Villa 11

This spectacular cottage was the setting for the big screen picture by 20th Century Fox, "How Stella Got Her Groove Back," starring Angela Bassett, Taye Diggs and Whoopie Goldberg. Taye Diggs later returned to Round Hill to marry the famous actress Idina Menzel

An ancient image of the beach near Round Hill Hotel & Villas
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Villa 12

Many musicals have been written in this cottage by the original owner Oscar Hammerstein. History tells us that it is at Round Hill where he met Maria von Trapp and "The Sound of Music" was written.

An ancient image of a photoshoot at Round Hill Hotel & Villas
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Villa 25

This villa was originally owned by dancer and entertainer, Adele Astaire. Later, John F. Kennedy edited and rehearsed his now famous inauguration speech by the pool. You can view several artefacts of his stay and speech in the villa today.

Our Staff

Hotel staff at Round Hill Hotel & Villas

We are proud of our lasting legacy, unmatched product and unique offerings at Round Hill, however nothing matches the pride we feel for our staff. We learned a long time ago that the most important part of our business is building relationships and this could not be possible without a dedicated team of enthusiastic and hospitable staff. To this end, every member of our team is committed to providing exceptional customer service at all times. With pride of ownership, our staff members boast lengthy years of service.

We are guided by our vision statement, mission statement and core values which define who we are and transcend to our customer promise.


To be the finest resort in the Caribbean by providing impeccable service and warm Jamaican hospitality in an environment of timeless elegance and understated luxury.


Building on the traditions and history of Round Hill, we seek to provide exceptional memories in a glamourous and stylish setting, personalized by highly motivated staff working with pride of ownership. Our caring commitment to the community ensures guests a uniquely Jamaican experience while preserving our natural environment and creating value for our shareholders.


  • Create exceptional memories
  • Build on our traditions
  • Recognize our guests' individual needs
  • Treat each other with respect and dignity
  • Maintain open communication at all times
  • Develop pride of ownership by investing in our staff
  • Provide a uniquely Jamaican experience
  • Be custodians of the environment
  • Commitment to the community
  • Value our shareholders


Timeless elegance. Understated elegance. Warm Jamaican heart.