Highland House
Montego Bay, Jamaica

One of Jamaica's most elegant private homes, previously Oscar Hammerstein Estate in the 1960's. This large 7000sq ft home set on 17+ beautiful and private acres.

Highland House's current owners have exquisite taste with high standards and careful attention to detail. The extensive renovations to this grand estate were made to preserve the magnificent history while updating the estate with the latest amenities. The décor reflects the island's Colonial British Indian heritage, incorporating carefully selected artwork, mahogany tables, collectibles, and imported antiques.

The estate can accommodate up to 12 guests for overnight stays and larger parties for special events.

There are 6 deluxe air conditioned bedrooms, each with en suite bathrooms 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 queen size 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.

Enjoy the large 16'x41' private swimming pool with roof top sundeck. 5 VCR's in house, entertainment center, CD player, SONY surround sound, speakers by poolside and sundeck. Guests also have membership privileges at Round Hill Resort.

The grounds are nestled in a mountain setting with mango trees, papaya groves, towering palms and vivid gardens. Highland House boasts some of the most astonishing views of Montego Bay. Its scenic pathways and secret stairways connect the estate's various environments, which are centered around a marvelous fresh water pool.

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.

Professional staff includes chambermaids, butler, cook, laundress, gardeners estate manager and personal concierge. The estates superb quality staff will ensure that your stay at Highland House is carefree.

Optional Services Include:

Events & Catering
The gourmet caterers and gracious servers of the Highland House staff will give your guests an event to remember.

On-site childcare is available upon request.

Private Driver/Guide
For a flat weekly or per-trip fee, you can have the house driver shuttle your party to activities around the island. The air-conditioned van is comfortable and accommodating for large and small groups. Driver Rates.

Gourmet Meals
While the meal plan is optional, it is highly recommended. Menus are created by award-winning chefs, prepared by the house cook of 20 years, and served in courses by the staff, the Highland House offers a luxurious dining experience. Enjoy special creations for breakfast, lunch and dinner. Menu for review.

In-House Spa
Top quality signature In-House Spa service is designed for deluxe pampering – everything from manicures and pedicures to hydrating massages using aloe from the property, all personalized to fit your needs.

Villa Rates

Minimum stay of 4 nights required
Surcharge of $35 pp/night for each addt'l guest over 12

15 April - 14 December
4 bedrooms $6,500
5 bedrooms $7,000
6 bedrooms $7,500


15 December - 14 April
(excluding Christmas and New Year's)
4 bedrooms $8,500
5 bedrooms $9,000
6 bedrooms $9,500 

-- New Year's Week --
1-12 guests . . . . . . . . . . . US$16,000
(15% staff gratuity based on US$9,500 rate)

-- Christmas Week --
1-12 guests . . . . . . . . . . . US$16,000
(15% staff gratuity based on US$9,500 rate)


  • Food and drinks are additional a meal plan is offered to order from the estate chef Meal Plan is based on US$55/adult/day and US$35/child/day

    The meal plan is not mandatory if guests prefer to purchase and bring in their own groceries and the cook prepare meals upon request

Please Add:

  • Staff Gratuity - 15% is added based on rental rate and collected with balance
  • Full-time driver service is available for guests that wish to tour the islandUS$750/week plus 15% gratuity (10 seat van)US$1,550/week plus 15% gratuity (25 seat van)  includes 1 complimentary tank of gas



  • A deposit in the amount of 50% of villa rental will Secure your RE-confirmed reservation.
  • Balance of Villa Rental, Staff Gratuity and Meal Plan is due at least 60 days prior to arrival, 75 days for Christmas or New Year's Weeks.
  • Please inquire for shorter/longer term rentals and cancellation policy.
  • All rates are subject to change without notice

Villa Reviews:

“The food was unbelievable. Every meal surprised us and we couldn’t wait until the next”
~ Laura, Michael and Drew

“By far the best massage I’ve ever had” 
~ David, New Jersey

“From mellow afternoon cocktails, competitive games of scrabble and ping pong – to wild evenings of spoons’ and chatter of secrets around the dinning room table – the entire trip was splendid!”
~ Jennifer, Atlanta, GA

“Nirvana! The experience here is blissful, memorable, tranquil. I will never sing a Hammerstein song again without putting my thoughts at the Highland House.”
~ Kimberly