Highland House

Montego Bay, Jamaica


Set among grand estates, coconut plantations, and thick bamboo forests, the Highland House features a panoramic view of the bay and village during the day that lights up to reveal a star-like scene at night.

Rising from the hills, the seven rooftops of the Highland House cover over 7,000 square feet. With six bedroom suites, the estate can accommodate up to 12 guests for overnight stays and larger parties for special events. Neighboring villas are available for additional overnight guests.

The Highland House is located in an exclusive area of Jamaica aptly named Content. Rich with history and made famous by the Royal Windsor Family, Content is in the parish of St. James located just 15 minutes from Montego Bay and the airport - but it seems worlds away.

Nestled in an idyllic mountain setting with mango trees, papaya groves, towering palms and vivid gardens, the Highland House boasts some of the most astonishing views of Montego Bay. From three stories, a groomed green lawn draws your eye toward the sea. Scenic pathways and secret stairways connect the estate's various environments, which are centered on a marvelous fresh water pool.

You would be hard-pressed to pick a favorite from the six Highland House suites. Each offers an en-suite bath, an individual ambiance, and a sitting area for quiet moments alone.

The Zen Room features a king-sized 4-poster cedar bed, spacious sitting area with satellite television and VCR, private bath, 2 sinks, shower, 4' x 8' linen-draped Roman tub, 5 ceiling fans, sliding doors to the lower lawn and a panoramic view of the sea.

The Jamaican Suite connects with the Zen Room. It's a smaller room designed for children with twin beds, en-suite bath (lower sink and toilet for a children's theme) walk-in closet, and private entrance. Wonderful collection of Jamaican and Haitian art.

The Owner's Suite features a queen-sized 4-poster mahogany bed, satellite television and VCR, dressing room and en-suite bath, and cedar plantation doors open to the private furnished terrace.

The Bird Room has a queen-sized 4-poster canopy bed, sitting area, satellite television, en-suite bath with shower and walk-in closet, and private deck surrounded by lush foliage. This room is totally secluded from the remainder of the house.

The Mahogany Suite offers a queensize bed, satellite television and VCR, large en-suite bath, French doors opening to a view of the lawn, jungle and sea. This room shares a covered terrace with the Deco Suite.

The charming Deco Suite features twin mahogany beds, an en-suite bath and a walk-in closet. It shares the covered terrace with the Mahogany Suite.

The numerous living spaces provide something for everyone. Enjoy a bird's eye view of the sea from the rooftop sundeck. Play card games or take an afternoon nap in one of the many quaint cushioned sitting areas on the terrace and around the pool. For movie time, the main gathering hall features comfortable sofas, high-peaked ceilings, and large plantation doors that invite the scenery and breezes inside. Downstairs you'll find a wet bar, darts, and pool table.

From candlelit dinners at dusk on the terrace to formal feasts at the grand round table, the Highland House dining areas are as delicious as the cuisine. Breakfast and lunch can be served next to the pool under a canopy of vines and greenery.

A short walk from the house takes you to the newly added pavilion designed to immerse you in tropical beauty. The wooden screened structure seems one with the landscape, and provides a secluded place for yoga, Pilates, ecstatic dance, and even special events.


Appoximate location



Babies welcome
Children welcome
Toddlers welcome
Pets welcome


12 people
4-6 bedrooms

Bathroom facilities

6 bathrooms


Outdoor pool
Ping pong table
Secure parking
Swimming pool


Coffee machine
Iron and ironing board
Music player
Satellite or cable
Washing machine
Built-in fans
Tailor your stayUpgrade your stay with extras when you book with our Travel Advisors.
Every stay includes
Sheets & towels
24/7 Support
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Home truths

The following additional costs apply, please speak to a Travel Advisor for more details.

$500 Security Deposit


For a complete set of policies for this home, please get in touch with our Travel Advisors.

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