Round Hill Hotel and Villas

A classic Jamaica stay that never shows its age

History runs through Round Hill Hotel and Villas almost as freely as the breezes off the Caribbean Sea. In the early 1950s, when Jamaica was coming into its own as a sought-after vacation destination, Round Hill Hotel and Villas opened its doors. The pride and joy of Jamaica-born entrepreneur John Pringle, the Montego Bay playground would go on to host the Kennedys for their honeymoon, serve as the site where The Sound of Music was written and provide the backdrop for the 1998 movie How Stella Got Her Groove Back.

Even today, take one look across the property’s social media feeds and you’ll see Hollywood stars and professional athletes who still can’t get enough of the property’s island charms. But you don’t need to have an agent to fall in love with the Round Hill. Its open-air suites, let-me-grab-my-camera views and pampering service are enticing to anyone looking to take a break from the ordinary.

Our Inspector's Highlights

  • The 27 villas are independently owned but they all have characteristics — semi-private pools, personal housekeepers, Elemis bath products, a pillow menu — that demonstrate a cool sense of cohesion around the 100-acre peninsula.
  • Maybe even more memorable than the Jamaica hotel’s setting is its service. From the young lady leading the fitness class to the gentleman pouring at high tea, everyone on staff makes you feel like a beloved friend who’s been gone for far too long.
  • As a show of just how committed the romantic resort is to personalized service, it has a policy of only hosting only one wedding per weekend.
  • The spa, which sits in an 18th-century plantation house, has seven treatment rooms where a host of localized options (Citrus Spa Manicure) and signature services (Pineapple Body Buff) are done.

Things to Know

  • Though this is exactly the kind of place you go to do nothing, if you ever feel so inclined to get out of your lounger, the resort offers tennis, provides shuttles to Montego Bay and happily transports you to neighboring Tryall Golf Club.
  • Couples may find the tranquility intoxicating, but families are more than welcome to enjoy the resort, too. Little travelers, especially, will enjoy the children-only activities, the Pineapple Kids Club and themed seasonal parties.

The Rooms

  • While all of the accommodations deliver an authentic Caribbean experience, if you want to feel an added sense of nostalgia, reserve Villa 10 (where Jackie and JFK honeymooned) or Villa 12 (originally owned by musical icon Oscar Hammerstein).
  • Villas may steal the headlines here, but the Ralph Lauren-designed Pineapple House, which features 36 guest rooms, is no slouch. Every unit includes four-poster mahogany beds, white stone floors, deep soaking tubs and waterfront views your Instagram followers won’t get enough of.

The Restaurants

  • The resort delivers dining options in the way of The Grill (modern Caribbean), Seaside Terrace (Jamaican, themed buffets) and the seasonal culinary standout, The Restaurant at Round Hill. The latter is where top chef Martin Maginley really showcases what he can do with organic herbs, local vegetables and fresh catches between mid-December and March.
  • If you don’t want to worry about any aspect of eating during your stay, you have the option of choosing between three different dining plans.
  • The drinks are great from all of the Montego Bay hotel’s many bars. But if you want a special splash of Caribbean sunset in your cocktail, make your way to the Infiniti Pool Bar around 5 p.m.

Outdoor pool
Getting There
John Pringle Drive Montego Bay, Jamaica
MBJ (10 min)   KIN (2 hr 50 min)  
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