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Round Hill Hotel and Villas


Private, timeless, oceanfront

John Pringle Drive Montego Bay, Jamaica (876) 956-7050 www.roundhill.com

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At a Glance

Despite its reputation for exclusivity, Round Hill is open to the public year-round with lovely, light-filled hotel rooms right along the water or sumptuous villas with views. 

Indagare Loves

  • The hands-on, longtime staff
  • The room’s easy-breezy décor by Ralph Lauren
  • The family-friendly vibe


A day at Round Hill looks like: a rustling of palm fronds on the roof, the whisper of sprinklers on the lawn, the twittering of songbirds in the garden, the jet trail of a plane arcing high above the cotton-ball clouds. Step out on the patio and see the sun beating down on the Caribbean Sea. While walking toward the main dining area, The Grille, the smell of coconut pancakes and freshly brewed Jamaican Blue Mountain coffee fill the air. Enjoy breakfast overlooking the sea, while planning for a fun-filled day, which may include lounging on the golden sand beach, snorkeling through coral reefs, trying backhand on one of the five tennis courts or taking a ride on the glass-bottom boat that leaves from the dock directly on the property.

Before Round Hill came to be what it is today, it was originally a 110-acre peninsula part of Lord Monson’s Round Hill Estate with a sugarcane plantation and later a coconut and pineapple grove. The hotel’s rich history and connection to the surrounding land adds to its unique character. Look out for pineapples, which have become an emblem of Round Hill and can be found sprinkled throughout the property.

Despite its reputation for exclusivity, Round Hill is now open to the public year-round. There are 36 lovely, light-filled hotel rooms located in the Pineapple House, complete with décor by Ralph Lauren himself. These ocean view rooms are ideal accommodations for those seeking a more traditional hotel-style setting. For something grander, behind the guest rooms are 26 privately-owned, uniquely-decorated villas (ranging from one-bedroom suites to six-bedroom villas) and are available for rent either in part or whole. Most villas are equipped with a private pool, while others are only steps away from the hotel’s infinity pool. Additionally, all villas have a dedicated villa staff that have been working at Round Hill for generations. By the end of your stay, the entire staff will feel like family (which is one of the reasons guests come back to Round Hill year after year).

Note: While villas include a butler, chef and kitchen, it is important to note that guests are not permitted to use stove tops.

At 3:30PM daily, guests can gather at the Cocktail Bar for afternoon tea featuring sandwiches, cakes, scones, tea and coffee while the kids are making a craft or going on a nature walk at the Pineapple Kids Club (for ages 7 and up). For those who prefer to unwind after a day in the sun, get a treatment at the Spa at Round Hill, located in a restored 18th Century estate home on 10-acres of beachfront lawn. Next door is the 2,300 square foot oceanfront fitness and yoga center with an open courtyard for outdoor stretches and cardio.

Before dinner, catch the sunset with a cocktail from the Ralph Lauren Cocktail Bar, with music from Round Hill’s resident pianist and vocalist. Once the sun has set, the lights twinkling from the Seaside Terrace Restaurant lure guests to enjoy a Caribbean-infused cuisine. Most dishes incorporate the fresh produce from Round Hill’s very own organic garden. While dining, local cultural shows and live music are performed, followed by dancing under the moonlight.

Who Should Stay

Families looking to find a life-long vacation spot, couples or individuals wanting a romantic weekend getaway without any technology (there are no TVs in the bedrooms) or those who appreciate a comfortable and familiar environment.

Indagare Plus Amenities

  • $100 USD Spa credit per stay
  • Breakfast is applicable for up to 2 persons per room.
  • Upgraded Room Category on Availability at Check-In
  • Late Check-Out on Availability
  • Complimentary WiFi Internet Access

Comments (1) OpenClose

One Comment

  1. E.K.
    2:43 pm | March 27, 2016

    we had a wonderful time. We had a terrific experience. Our villa was wonderful – the bathrooms were news and beautiful, the pool was lovely and we had a lawn ideal for children. We thought the ac was a little unpredictable but still fine. We loved the landscaping at the villa and the whole property. We felt that the hotel was very private and yet there was so much to do. The infinity pool is absolutely spectacular. The spa was fantastic but a bit overpriced. The beach and sports were excellent. We took tennis lessons and Steve the pro was amazing. We thought the food was exceptional. I took particular note of their greens and vegetables which were perfect – I have not found this in any other Caribbean resort. We thought the service was terrific too. I would say the only criticisms were – burger surprisingly not good but all other food was terrific, airplane traffic was a bit much and planes fly directly overhead and often and overpriced spa though the services were extremely good. So – we would highly recommend!

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