If you like old fashioned tropical glamour with a view almost as good as that of the opening sequence of the Sound of Music then Hammerstein Highland House is for you. Built in the 1950s by the Oscar Hammerstein, the lyric and book writing partner of Richard Rodgers, and maintained by current American owners, it has the timeless classy vibe of a place trying just hard enough. The décor is largely white with splashes of bold pastels that bring Jonathan Adler and Kelly Wearstler to mind – without the pretense. The staff is sublime, quiet and efficient and the fresh locally sourced meals by the chef – with ingredients from the property’s organic garden are full of traditional Jamaican zest. The pool is fresh as a lake, each room generous and unique. The villa is a ten minute drive up a hill from the bustle of overwrought Montego Bay with its built up beaches and traffic. What a difference a mountain road makes. Yet it’s all happily less than a half hour from the airport and the intensely posh Round Hill — for dinner among the excessive and elite. Unique, divine!

Gardens & Grounds

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 around a marvelous fresh water pool.

Bedroom Suites

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, 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 which can be converted into a king, 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, dressing room and en-suite bath, and cedar plantation doors open to the private furnished terrace.

The Bird Room has a king bed that can be seperated in two twins, 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, 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 which can be converted into a king, an en-suite bath and a walk-in closet. It shares the covered terrace with the Mahogany Suite.

Living Spaces

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.

Dining Areas

From candlelit dinners at dusk on the terrace to formal feasts at the grand roundtable, 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

The Pavilion

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.