Elegance, seclusion and history meet at these elite resorts 

Villa Escapes

Round Hill is a classic stay near Montego Bay
Jamaica

Pre-dinner cocktail in hand, I browse a collection of vintage black and white photos displayed on the wall within the candlelit bar at Round Hill. Among the images of couples dancing, tanned families and hotel guests relaxing on villa verandas, I recognize Ralph Lauren, Michael Douglas and a young Pierce Brosnan, a towel draped over his shoulders. With piano music tinkling in the background, the mood hearkens back to an elegant, timeless era.

Villa resorts such as Round Hill are growing in popularity among luxury travellers looking for privacy, attentive service and decadent comforts. There’s no scrambling for a beach lounger, no buffet lines or shared swimming pools. Guests enjoy the amenities of a world-class resort along with the seclusion of a private estate. Here are three villa resorts – each with posh pedigrees -worth checking out near Montego Bay, Jamaica.

Round Hill Hotel and Villas

Villa Escapes

John F. Kennedy and Jackie Kennedy
honeymooned in four-bedroom Villa 10
Photo: Michele Peterson

Built in 1953 and situated on a sprawling 45 hectare estate west of Montego Bay, Round Hill Hotel and Villas has long been popular among jetsetters, style icons and celebrities due to its seclusion, prime oceanfront setting and understated glamour. The property features 36 guest rooms in the Ralph Lauren-designed Pineapple House and 27 privately owned villas, available for rent in full or as suites.

Tucked among the rolling hills of the property, stone walkways wind through cascades of bougainvillea to hideaways such as Villa 11, featured in the film “How Stella Got Her Groove Back” starring Angela Bassett, Taye Diggs and Whoopi Goldberg, and Villa 12, where Oscar Hammerstein wrote “The Sound of Music” after meeting Maria von Trapp.

Villa Escapes

Enjoy seclusion at the private pool of
Villa 10 at Round Hill
Photo: Michele Peterson

My own temporary digs in Villa 10 are no less storied when it comes to star power. JFK and Jackie honeymooned in the same bedroom I’m in (aptly named the Kennedy Room). It was a favourite of Ralph Lauren, and the preferred stay for Sir Paul McCartney when he wasn’t paddling his kayak in the bay.

At Villa 10, mornings begin with a leisurely breakfast served on the villa wrap-around terrace, prepared by staff who can whip up an American breakfast or the local specialty of ackee and salt fish. Then, options include whiling away the day at the private pool, taking a tour of the bay in a glass-bottom boat or getting active with water sports at the beach.

Villa escapes

Expansive terrace of Villa 10 at Round Hill

It’s also easy to recharge thanks to a bevy of health, wellness and spa resources. The Spa at Round Hill, located within a restored 18th century plantation house overlooking the Caribbean, offers treatments featuring natural Jamaican ingredients as well as the Elemis product line. Complementing this serene atmosphere is a new gym and juice bar offering healthy beverages, refreshing smoothies and wheatgrass shots. For wellness enthusiasts wishing to dine at the spa, the new food menu features light options such as chilled gazpacho, chicken wraps and arugula salad using organic ingredients.

The Tryall Club

A short jaunt along the coast rests another historic luxury resort where the heavenly scent of ylang-ylang trees (a key ingredient in Chanel No. 5 perfume) fills the air. Founded in 1957, The Tryall Club pairs seclusion and luxury living within 75 privately owned estate villas offering a mix of stunning views, private swimming pools and unique architecture. Each villa comes with dedicated staff including a butler, chef, housekeeper, laundress and gardener.

Villa Escapes

Spacious luxury villas at The Tryall Club can accommodate large parties and families
Photo: Michele Peterson

Meandering along the private coastline and through vast botanical gardens is the 18-hole Audubon-certified Tryall Golf Course. The renowned Tryall tennis club features nine championship courts, some lit for night play, as well as a world-class academy. A Kid’s Club, a range of watersports and Afternoon Tea at the Great House, round out the offerings for all ages.

One of The Tryall Club’s largest luxury villas is now even more impressive. A $2 million renovation of the 10-bedroom estate villa “Create Abundance” added a poolside bar and gymnasium near its outdoor heated swimming pool, children’s playground and basketball court. The popular five-bedroom “Sunset” villa, located on a private beach on the edge of the Caribbean, has also been expanded to include an ocean-facing two-bedroom cottage linked by covered walkway to the main house.

Half Moon Resort 

Founded in 1954, this gem located in the parish of St. James on Jamaica’s North Coast has long been the top spot for visiting British royalty (and a Canadian prime minister or two) and it hasn’t lost its cachet. Prince Harry enjoyed a villa retreat at Half Moon during his first official royal tour marking the Diamond Jubilee of Queen Elizabeth II. In addition to its 197 guest rooms, suites and cottages, the resort features 31 luxury villas, offering a relaxed Caribbean ambience ideal for families, groups or friends.

Villa Escapes

Fine dining at atmospheric and historic Sugar Mill Restaurant
Photo: Half Moon

Decked out with private swimming pools and ranging from four to seven bedrooms in size, each luxury villa at Half Moon is staffed with a butler, cook and housekeeper. Golf carts and shuttles (or bicycles if you’re feeling active) offer easy access to a full range of resort amenities and facilities such as beaches, an Equestrian Centre, tennis and squash, the award-winning Half Moon Golf Course and the Fern Tree Spa.

Half Moon’s range of dining options includes Sugar Mill restaurant, one of Jamaica’s finest and most atmospheric restaurants. Opt for a table on the stone patio beside the 17th century sugar mill and its restored water wheel and enjoy a menu that marries modern Jamaican flavours with international flair in signature dishes such as Solomon’s jerk brochette, flambéed with aged rum.

Whether you’re looking for a hilltop hideaway for two or an ultra glamorous space to party, each of these legendary resorts offers a perfect mix of Jamaican hospitality, privacy and luxury amenities.

Travel Planner

Air Transat: Offers non-stop service from Montreal to Montego Bay, Jamaica. www.airtransat.com

Club Mobay: Enjoy complimentary beverages and snacks, Wi-Fi, luggage assistance and escorted fast track VIP access through Immigration and Customs at Sangster International Airport, Montego Bay and Norman Manley International Airport, Kingston at Jamaica’s premier airport lounge. www.vipattractions.com

Round Hill: Round Hill Hotel and Villas, offering 27 individually-owned villas and the 36-room Pineapple House designed by Ralph Lauren, is located west of Montego Bay, a 20-minute drive from Sangster International Airport. www.roundhill.com

The Tryall Club: www.tryallclub.com

Half Moon Bay: Sugar Mill is located at the edge of Half Moon Bay Resort.  www.halfmoon.com

Visit Jamaica: The official tourism site offers a wealth of information on activities, travel and attractions. www.visitjamaica.com