Situated on Montego Bay, Round Hill Jamaica is a classic in its own right, a resort that evolved from a cluster of private homes built by superstar entertainers (such as Oscar Hammerstein, Mrs. Fred Astaire, and Noel Coward) back in the 1950s.

These luminaries brought more luminaries and their idyllic community located on the Round Hill pineapple plantation became an intimate and exclusive hideaway. Now, celebrities such as Demi Moore and Paul McCartney take their families to relax at this world-class Jamaican resort. We won't mention the myriad other celebs who return over and again with their kids -- it wouldn't be right to deprive them anonymity in such a down-to-earth getaway.

Luxurious Lodging at the Laidback Round Hill Resort

In an haute timeshare concept, Round Hill manages 27 super-luxe two- to five-bedroom, freestanding villas and rents out individual suites when available. Each is unique, tended by its own housekeeper, gardener and cook.

The bright, crisp decor is appointed 'just so' under the influence of fellow homeowners Ralph and Ricky Lauren. Many villas, each within a few minutes' walk of the gold sand beach, have their own plunge pools as well.

For families who prefer to be 'guests' of the very rich rather than live their lifestyle, there are spacious, newly renovated rooms in the Pineapple House, a two-story stucco hotel whose broadstripe window canopies say more about the place than anything.

The Pineapple House contains 36 oceanfront rooms featuring more classic Lauren furnishings, a four-poster mahogany bed, and white stone floors. There is also a grand suite.

Round Hill's Organized Children's Activities

In its isolated cove near busy Montego Bay, Round Hill offers watersports, a pool, 5 tennis courts and easy access to golf and island sightseeing.

In summer, from 9am-5pm, the Pineapple Kids Club offers nature walks, talent shows, reggae and tennis lessons, and other activities for kids from 3 to 12-years-old.  Depending on the number of children in-house, activities and crafts projects are organized by the trained staff, especially after dinner.

For some families, it's not about the kids programs or the nanny service that comes bundled in many of the summer promotion packages.  But as one of the frequent guests (mom of 3-year-old twins and an infant) confided, "It's wonderful to get the children away from their toys and TV and back to a natural kind of play."  She added, "Here they roam the beach, ride the donkeys, play with the staff and wind down from their usual over-stimulated routine. We feel it gives them a chance to vacation the way we did when we were kids."

Dining at Round Hill Jamaica

The gourmet menu changes nightly; some evenings it's a torch-lit beachside grill, others Jamaican cuisine, dancing and music. The Jamaican food, as are all dishes, is imaginatively presented using the freshest ingredients. Much of it is locally sourced from the nearby Pantrepant Farm owned by Chris Blackwell of Island Resorts, and cooking demonstrations are a popular pasttime. 

Meals are also presented in the indoor restaurant or on the broad, beachview terrace, with early dinners available to younger children. Depending on season, a daily meal plan allows families to dine at the resort without much thought about its pricey menu.

Some evenings children disappear with the bevy of longtime nannies, who entertain and feed them in the lounge while parents gossip and trade cigars. On these evenings, guests who've met or reunited continue their conversations into the wee hours in the cozy, wide wicker armchairs at the piano bar named Lauren.

Trip Planning Details for a Round Hill Resort Vacation

Despite the potential for an overwhelmingly obnoxious atmosphere, Round Hill is truly delightful. I imagine that when I return, I'll sit and watch the children searching the gold sand beach for crabs, running up and down the pathways leading to the various villas, leafing through books of the island's history in the paneled library.  Or, maybe they will be playing quietly with others who look upon Round Hill as their second home.

Round Hill Jamaica is located in Hanover Parish at John Pringle Drive, Montego Bay, Jamaica, West Indies.

Villas range in price up to $5,000 per night depending on season and size of accommodation. Rooms are the Pineapple House begin at about $400/night per double.  Summer is a relatively new season at Round Hill, which closed for many years while regulars went to the Hamptons or the south of France, and staff went to work on Mackinac Island. You'll find special values, such as an adjoining room for kids at half price, at this time of year.

For more information, contact your travel agent or get in touch with Round Hill Jamaica (876/956-7050; 800/972-2159)

Photos of Round Hill by David Massey, courtesy of Round Hill Jamaica Resort.