THE BLOG
12/25/2012 12:18 pm ET Updated Feb 24, 2013

3 Unforgettable Villa Vacations in Jamaica

Sharing costs with friends or family can make these opulent villas more affordable for a special vacation.

The island of Jamaica is a popular tourist destination because of its tropical climate, craggy coastline with white sandy beaches, lush tree and ground vegetation, verdant golf courses, zesty foods paired with reggae and rum and long tradition of warmth and hospitality.

A one-week stay at a five-star, professionally staffed villa in Jamaica doesn't come cheap --especially during high season, which runs from mid-December to mid-April. But the costs of a sybaritic experience can be whittled down substantially when it's split among one or more families, or a tribe of friends.

Each of these exceptional properties is uniquely steeped in history, offering privacy, security, luxury amenities and great views. They are self-contained playgrounds that can comfortably accommodate 10 to 18 guests for a mix of rest and relaxation, on-premise activities and nearby exploration -- making them perfect venues for celebrating a milestone birthday, anniversary or a memorable family reunion.

Sugar Hill

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Dining Al Fresco at Sugar Hill

The sprawling one-level private villa was built about six years ago. Owned by an American family, its spacious, well-designed layout is conducive to guests who want to spend time together and may also want to spend time apart. It has a large, welcoming living room with a peaked ceiling at its center. Two master suites and two guest bedrooms flank it at each side, all with hand-carved, mahogany four-poster beds and beautiful ensuite bathrooms; each master also has an adjoining study/office, and one has an outdoor shower.

An expansive wraparound veranda with wood-shuttered, floor-to-ceiling doors affords commanding views from every room, overseeing the large pool and gracious deck; the carefully pruned tropical garden with blooming plants and fruit trees; and the sparkling Caribbean at the bottom of the hill. The unattached three-bedroom guesthouse nearby has a recreation room with pool, ping-pong and foosball tables.

Guests can dine al fresco under a flower-covered trellis on the terrace, in the formal dining room or at the top of the romantic two-story sugar tower of hand-cut stone. There is also a hot tub, a fully equipped gym, an open-air pottery studio beneath the house and a stone pizza oven outside the kitchen. The tasteful furnishings and decor of Sugar Hill reflect the owner's appreciation of the artistic and cultural heritage of Jamaica. Museum-quality paintings, sculptures and whimsical folk art can be found both indoors and out.

Sugar Hill is one of 67 privately-owned estate villas, ranging in size from two to seven bedrooms, set on the 2,200 acres of land that comprise the Tryall Club, former home of the Johnnie Walker golf championship. Once the site of a coastal fort built by the English to defend against Spanish and French invaders and pirates, it later became a working sugar plantation and then a coconut farm. A stone aqueduct and functioning waterwheel on the grounds date back to 1834.

For a nominal fee ($100 per person, per week) guests at Sugar Hill become temporary members of the Tryall Club, which includes access to the 1,000-foot private beach with a café on the water, reduced fees at the 18-hole golf course, nine all-weather tennis courts, a kid's club and fitness center and the historic 18th-century Georgian Great House, which offers dining and afternoon tea.

Rio Chico

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Relaxing Family Room at Rio Chico

Both the villa and the grounds of Rio Chico have the charming patina of age. Originally built in the late 1800s as a guesthouse for nearby Dunn's River Falls, it went through a series of owners until 1992, when it was sold to its current owner, Gordon "Butch" Stewart, owner of Sandals Resorts and Beaches Resorts, as a family getaway. Stewart tastefully refurbished the house, which is one of four private villas in Jamaica now managed by Sandals.

Upon entering the iron gates and long driveway of Rio Chico, guests are enveloped in a private park-like enclave bordering the Caribbean Sea. Running streams, rivers and cascading waterfalls can be seen and heard throughout the lush, tropical 14-acre property dotted with stone bridges and lily ponds.

The two-story, colonial-style main house has six large bedrooms, which are tastefully decorated with beds covered in Anichini linens. Each room has a private bath and full-length patio overlooking the beach, the sea or the exquisitely landscaped Italianate gardens with stone walls. For privacy, the house is divided, with two separate stairways leading to the front and back bedrooms. An additional bedroom (with ensuite bath) is located on the entry level.

The expansive living space on the first floor includes a formal sitting area; a chandeliered dining room; an informal family room with a billiard table and mirrored, fully stocked bar; and a media room with a library of DVDs. Many of the ceilings are hand-painted by a local designer.

A self-contained two-bedroom cottage is only a two- or three-minute walk from the main house, and is ideal for older teens, or nannies and young children. A charming open-air chapel (made of stone) sits on the eastern side of the property. Rio Chico has welcomed many international celebrities and dignitaries over the years, including UN Secretary General Kofi Annan, Congressman Joe Kennedy, Donatella Versace, Robin Williams, Boy George and Wesley Snipes.

The property has 2,000 feet of protected shoreline with two white sand beaches, two freshwater swimming pools filled by a tributary to the falls, a heated Jacuzzi and a lighted tennis court. Guests can use the "toys" available on site to participate in water sports, which include snorkeling, sailing, kayaking and aqua cycling.

Most impressive, however, is the attentive and professional staff who cater to the whim of every guest -- including a butler, lifeguard, laundress, housekeepers and chef, Ignazio Podda, who hails from northwestern Italy. Chef Podda sits down with guests upon arrival to create inspired menus incorporating both Jamaican and continental dishes. Each evening, the house team finds a magical new dinner setting, either on the beach, in a river or on a romantic patio overlooking the sea.

Fleming Villa at GoldenEye

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Master Bedroom at the Fleming Villa

With no sign marking its entryway, guests need to know where they are headed to find GoldenEye Hotel and Resort. Although this might hint of exclusivity, the tone at this 21-unit boutique resort set on 52 rustic acres is casual and friendly. Both the villa and the nearby wood-framed beach and lagoon cottages appear natural and unpretentious; they almost fade into the densely treed forest.

The Ian Fleming Villa is the historical jewel of this seafront property, now owned by legendary music producer Chris Blackwell, who many credit with introducing reggae music to the world. Fleming entertained playwright Noel Coward and Prime Minister Anthony Eden here and, more recent celebrity visitors have included President and Secretary of State Bill and Hilary Clinton and Pierce Brosnan. .

Ian Fleming came here to work from January to March, producing one of his James Bond adventure novels every year for 14 years. It's hard to imagine the author not being distracted by the picture window that opens onto a sunken garden and the sea. Fleming's original writing desk remains in one of the bedrooms, and aficionados can find other interesting historical artifacts on premises.

The villa, originally a three-bedroom home, has been expanded to five bedrooms set around a pool area (the main house with three bedrooms, and the pool house and the sweet spot, each with one) and a large media room with a stocked bar. All the bedrooms have both indoor and outdoor bathrooms.

Guests can arrange to have their dinner served at Fleming Cave on the beach, but they can also take advantage of the hotel amenities, which include a spa, a sandy beach and pool, a swimmable lagoon, a glass-bottom boat, kayaks and two restaurants: the Bizot Bar, open for breakfast and lunch, and the Gazebo, a tree-house style restaurant that excels at Jamaican fare. Blackwell also operates several other eco-friendly Island Outpost properties on the island, including Strawberry Hill, The Caves, Geejam and several private villas.

If you go:

Check these websites for availability and rates, which vary by season. Be sure to inquire about any extra costs, such as transportation to and from the airport, meals, greens fees, and off-site tour excursions.

Sugar Hill

Located 25 minutes from Montego Bay Airport atop Barnes Hill on Sandy Bay, Hanover Parish.
Sleeps 14 adults, prices start from $2,500 a night depending on season. Shared cost, per couple, for seven couples: approximately $357 per night.

Rio Chico

Located 90 minutes from Montego Bay Airport, outside Ocho Rios in Saint Ann Parish. Sleeps 18 adults, prices start from $6,430 a night. Shared cost per couple, for nine couples: approximately $714 per night.

Fleming Villa at GoldenEye

Located 73 miles from Montego Bay Airport, 20 minutes from Ocho Rios on Oracabessa Bay in Saint Mary Parish. Sleeps 10 adults, prices start from $5,500 per night, including a full breakfast. Shared cost per couple, for 5 couples: approximately $1,100 per night.

Irene S. Levine, PhD is an award-winning travel writer and member of the Society of American Travel Writers (SATW). You can follow her blog for travelers over 50 at More Time To Travel or on Twitter.

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