Three Posh Vacation Villas in Jamaica


Sharing costs can make these opulent vacation villas in Jamaica more affordable for a special get-together of friends or family.

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

A one-week stay at a five-star, professionally staffed villa in Jamaica doesn’t come cheap. This is especially true during the 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. Coupled with opportunities for nearby exploration, they are ideal venues for celebrating a milestone birthday, anniversary, or a memorable family reunion.

Sugar Hill

Sugar Hill in Jamaica
Pool at sunset at Sugar Hill Villa in Jamaica

The sprawling one-level private villa is 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 each side, all with hand-carved, mahogany four-poster beds and beautiful ensuite bathrooms. Each master also has an adjoining study/office; 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 has blooming plants and fruit trees, and the sparkling Caribbean is at the bottom of the hill.

An 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, the 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, 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

Rio Chico in Jamaica
Relaxing family room at Rio Chico Villa in Jamaica

Both the villa and the grounds of Rio Chico have a charming patina of age. Initially 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 late owner, Gordon “Butch” Stewart, owner of Sandals Resorts and Beaches Resorts, as a family getaway.

Stewart tastefully refurbished the house, which along with other private villas in Jamaica, is 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 an 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 setting 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 a chef. The chef 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

Ian Fleming Villa at GoldenEye in Jamaica
Bedroom at the Ian Fleming Villa in Jamaica

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 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. Other 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 for 14 consecutive years, producing one of his James Bond adventure novels every year. 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 the 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.


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.

Rio Chico

Located 90 minutes from Montego Bay Airport, outside Ocho Rios in Saint Ann Parish. Sleeps 18 adults.

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.


[This article was published in The Huffington Post.]

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  1. On such a cold and dank New England night, this post was most welcome. I have never been to Jamaica. This post allowed me to imagine I were there, so thank you.

  2. I look outside and it’s cold and gloomy — then back at your incredible photos. These places look like pure heaven.

  3. Wow that’s quite posh, love the details and beautiful appointments add a chef and what’s not to like. I guess I’ll have to round up 14 of my best friends to make it more affordable to my standards 🙂

  4. Villas are my preferred type of accommodation. You’ve got some lovely ones here, Irene.
    Tryall’s a stone’s thrown from where I am, I drive by every so often but I’ve not stayed in any of their villas. It just doesn’t make economic sense so I wait until I can get several friends together and split the rental cost.

  5. Sitting here in the Cold part of winter I drooled over all of your pics from Jamaica….I so wished that I could be there right this minute, sitting on the private beach of Sugar Hill ordering a cold drink from the cafe 🙂

  6. Herb and spice mixtures like this can also be used as gifts.
    Africa and India started to supply Middle Eastern civilization with spikenard
    and ginger. Oftentimes, such food can be bought in different local stalls together with the tarik (pulled tea).

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