Highland House - Montego Bay 5BR

From $1,000 / night

Description from the manager

  • House
  • 5 bedrooms
  • 12 bathrooms
  • Sleeps 10

Bedrooms: 5

Bathrooms: 12

Sleeps: 10

Type: House

Highland House - Montego Bay 5BR


Oscar Hammerstein Estate - fabulous refurbishments makes this one of Jamaica's most charming and lavish homes.

Wait! Why you should book this villa?

You have found a villa that has a first class Tryall Club Beach and Resort membership available for all guests!

(Direct bookings with Jamaican Treasures )

The Tryall Club is one of Jamaica’s premier private resort club offering:

Complimentary beach, 9 tennis courts, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, art gallery, jogging trail, afternoon tea & Manager's Cocktail Party. For various fees: Reduced green fees for world championship golf, tennis lessons, ...Read more

About the manager

Jamaican Treasures

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Highland House - Montego Bay 5BR
Wiltshire, Jamaica

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Oscar Hammerstein Estate - fabulous refurbishments makes this one of Jamaica's most charming and lavish homes.
Wait! Why you should book this villa?
You have found a villa that has a first class Tryall Club Beach and Resort membership available for all guests!
(Direct bookings with Jamaican Treasures )
The Tryall Club is one of Jamaica’s premier private resort club offering:
Complimentary beach, 9 tennis courts, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, art gallery, jogging trail, afternoon tea & Manager's Cocktail Party. For various fees: Reduced green fees for world championship golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, beach parties Mon-Wed-Fri. For discerning guests the luxury and hospitality of a true villa lifestyle. Read the amenties you will enjoy here. Tryall Club Resort
Highland House is one of the most beautiful luxury villas Jamaica, an exquisite estate with an enchanted history. The six bedroom Jamaica villa is located on 17 acres of lush hillside terrain that overlooks the sparkling Caribbean Sea. Vacationing at Highland House is a memorable and extraordinary experience due to picturesque scenic beauty, luxurious accommodations and lavish service.
Highland House was originally constructed for the English actress, Gladys Cooper in the 1940s. Since then, the villa has seen numerous momentous occasions. One of the most historic occurrences was when the lyrics to ‘The Sound of Music’ theme song were written from its terrace by the second owner and Broadway legend, Oscar Hammerstein II. Hammerstein and his wife used Highland House as a retreat to get away from New York and its fast-paced lifestyle. They entertained frequently, inviting their celebrity friends to enjoy the tropical environment and the fabulous scenery.
The current owner of the Highland House, Brenda Isaac of Atlanta, has carried out extensive renovations recently ensuring that the magnificent history of the villa is preserved, while adding the latest amenities and facilities. Brenda led a team of leading artists and distinguished interior designers to fulfill her vision of creating a series of charismatic environments complemented by elegance and comfort. The décor incorporates meticulously selected artwork, collectables, mahogany tables and imported antiques that reflect Jamaica’s British Indian heritage. Most of the period furniture from Dorothy Hammerstein’s collection has been retained, along with Oscar Hammerstein’s ingenuity. Highland House is even more spectacular in its current form, reflecting artistic influence, sophisticated beauty and contemporary luxury.
Vacationing at one of the most spectacular villas in Jamaica is a luxurious experience indeed. The elevated views, elegant accommodations and the gracious hospitality of the staff make Highland House the perfect escape with family or a special group of friends. The staff ensures that guests receive individual attention with privacy when desired, while the activities available locally offer a diverse collection of adventurous pastimes. It is also the perfect destination for romantic getaways and honeymoons. Fresh tropical flowers, indulgent massages and candlelit dinners make any couple’s time together truly magical. Solitary travelers seeking star treatment and ample space to themselves also love Highland House. Quiet reflection, soul-searching and relaxation are at their best done in the serene environment at this villa.
Couples looking for the perfect setting for their wedding, the most special day of their lives, find Highland House to be a fairytale setting. Wedding guests cannot help falling in love with the meandering driveway with borders of bright flowers and the luxurious ambience of the villa. The villa’s staff is trained to receive the guests graciously and attend to their every need. Highland House weddings are glamorous, beautiful and charming, particularly when the couple takes their vows in the midst of the rainforest or by the glorious pool setting.
The Jamaica villa also provides an amazing setting for reunions, where people come together from all parts of the world. The six bedroom suites are built in four individual structures, providing a sense of privacy. Several living areas provide the opportunity to reconnect conveniently. Guest can enjoy cocktails under a star filled sky on the rooftop terrace, or enjoy lavish island cuisine by the pool, while they are entertained by a live reggae band. Highland House can organize casual and formal parties, gatherings and events.
Highland House is one of the few villa rentals in Jamaica that has been designed for meetings and retreats, with a secluded pavilion in the trees that is perfect for yoga classes and group meetings. The serene environment and scenic beauty, complemented by the staff’s gracious hospitality makes each event memorable. Yoga and spiritual teachers repeatedly choose this amazing villa for their group retreats. The pavilion is ideal for instruction and meditation, soothing the body, mind and soul with luxurious suites, uplifting views and on-site spa treatments.
Team-building efforts can be carried out at Highland House in the best possible manner as team members find common interests in the fantastic scenery, the delectable cuisine or local activities, such as horseback riding, waterfall hiking or catamaran cruises. Team connections built after only a few days at the beautiful setting will be long-lasting. Meetings and sessions can be organized for thinkers and executives from across the globe to work together in the picturesque, private and stress-free environment. The villa’s staff will organize every aspect of the stay, ranging from meals and transportation to entertainment, so that guests can brainstorm in the same setting which inspired Oscar Hammerstein.
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This has got to be one of the most gracious homes in Jamaica today...
With the careful attention to detail from this current owner, the service from her staff is superb in every way. This owner has a high standard in the design of the interiors. From the fabrics of the soft furnishings specially selected by her team of interior designers from Atlanta, the soft fern leaves which delicately shadows the walls of the master bedroom, to the special menus which have been created by professional chefs from Los Angeles and is prepared specially for the guests who stay at this most wonderful home which is so steeped in history.
Highland House is an exquisite private home, owned by the famous Dorothy and Oscar Hammerstein in the 1960's.
Island Home Magazine has featured this wonderful home in their magazine. In 2000, the current owner began extensive renovations to restore this magnificent villa to its former majestic grandeur. In her vision for the restoration, the owner led a team of Atlanta artists and decorators to artfully redesign each room's décor. The result is a splendid mix of artistic creativity woven together with a playful eye. These renovations have taken Highland house to a new level of luxury. With this team of professional designers, this property is one of the most glamorous estates in Jamaica.
Oscar Hammerstein II is best remembered for his collaborations with Richard Rodgers, including the Broadway musical phenomenon of 1949, "South Pacific." Hammerstein spent his days in Jamaica writing the lyrics to "South Pacific" from this fabulous estate, Highland House. This was his retreat from his New York City home. There is a wonderful sunroom with glorious views, and it is here where Sarah Churchill and Noel Coward played bridge with Dorothy Hammerstein on many relaxing Jamaican evenings.
Luxury Vacations
A private vacation at the Highland House is the pinnacle of luxury. The elegant accommodations and elevated views are perfectly complemented by the gracious hospitality of an on-site staff. Escape with a group or alone - for a long weekend or several months - to mark a milestone or to simply indulge.
Friends & Family
The Highland House creates an incredible shared memory, while also providing the privacy you desire when on vacation. The experienced staff ensures your guests receive individual attention, and the local activities offer an array of adventures.
Romantic Getaways
For honeymoons and special getaways, this paradise is a favorite. With long, indulgent massages, fresh tropical flowers, and candlelit dinners overlooking the sea, your time together is as magical as the setting.
Solitary Escapes
Solo travelers enjoy the ample space and star treatment of the Highland House. Leisurely explore the scenic grounds and take in the unique environments. Experience a signature massage from your choice of balconies. A special place for soul-searching, quiet reflection, and relaxation.
Weddings and Celebrations
High in the hills overlooking the sea, the Highland House offers a fabled setting for your event. As guests enter the meandering driveway bordered by bright blooms, they'll know they're in for a treat. The Highland House butler will greet your guests and an experienced staff will attend to their every need.
Yoga Retreats
The latest additions to the Highland House have been designed with retreats and meetings in mind. A secluded pavilion is tucked in the trees, where yoga classes and group meetings can take place among serene beauty. Numerous private sitting areas encourage conversation and bonding. And with the staff's gracious hospitality, island life has never been more relaxing.
Yoga & Spiritual Journeys
Yoga and spiritual teachers are invited to make this tropical paradise the site of your next group retreat. The property's pavilion offers the ideal setting for meditation and instruction. Soothe mind, body and soul with uplifting views, luxurious suites, and on-site spa treatments.
Guests of the Highland House enjoy complimentary service from an 8-person staff, including a butler, chambermaids, gardeners, and house manager. Thanks to the staff's attentive expertise, your stay at the Highland House is carefree.
Complimentary Services Include:
From serving drinks to arranging activities, the Highland House butler will take care of the logistics and details during your visit.
Maid Service
The Highland House features fulltime maid service.
Wash/fold Laundry
Enjoy freshly cleaned clothes daily. Simply place your items in the hamper and find them waiting on your bed the next morning
Coffee Service
Wake up to a freshly brewing pot of Jamaican coffee in your room every morning.
In addition, the Highland House features optional services you can request as needed.
Optional Services Include:
Gourmet Meals
While the meal plan is optional, it is highly recommended. Nowhere in Jamaica will you find such consistently delicious cuisine. With menus 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.
In-House Spa
The signature spa at the Highland House is designed to fulfill your dreams of pampering. From manicures and pedicures to exceptional massages featuring aloe from the property, you and your guests can choose your pleasures for a personalized experience.
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.
Meal Plan
There are 2 choices for Meal Plans at Highland House. You can simply go on the grocery plan were the cost of the meals, are the items bought directly from the supermarket. The Cook will make the purchases (or you may join the cook at the supermarket if you wish!) and the bills will be accumulated and shown to you. You may simply pay the amount of the bill a day or two before you depart the villa.
If you prefer to go on the Meal Plan, then guests are asked to select a meal plan in advance and prepay for groceries. Read more below on this:
Meal Plan:
The meal service is a defining characteristic of the Highland House experience. Designed exclusively for the estate by award-winning chef Vernon Simon, the menu blends international and local fare for a medley of delicious flavors. Breakfast and lunch are served under the vine-covered pergola by the pool, while dinner is formally presented at the grand roundtable. Attire can be as casual as your mood.
Plan Includes
3 Meals per day*
Iced tea and water
In-room coffee service
Unlimited fruit smoothies
*Breakfast and lunch are chef's choice. The group dinner can be chosen from the available menu.
Age 13+ $55 per person per day
Under 13 $35 per person per day
*No charge for children 3 and under
Hors d'oeuvres upon request at $5 pp
Please note: Costs of soda, alcoholic beverages, mixers, and snacks constitute an additional charge based on consumption. Guests are asked to select a meal plan in advance and pre-pay for groceries. Staff must be informed of dietary restrictions at time of menu selection. Refunds of $10 for breakfast or lunch and $20 for dinner are given if meal is cancelled with 48-hour notice.
The Highland House setting soothes the mind and soul, but it's the spa services that bring your body to a state of total relaxation. With aloe gathered from the property, the masseuse will nourish your skin after a long day in the sun. Secluded from the house, a newly designed spa area offers an outdoor shower and the perfect place to take in the dramatic view of the sea while receiving your personalized treatment.
Spa Services Available:
Manicure pamper your hands with this full manicure including cuticle repair, buffing, smoothing, and polish. Acrylics not available.
Pedicure the complete treatment includes cuticle repair, smoothing and shaping of nails, removal of dry skin, and light massage.
Facial enjoy a deep cleansing and revitalizing treatment to invigorate your face and refresh your skin.
Massage design your own massage to treat the part or parts of your body that need it most. Choose from a deep muscle or Swedish massage that can be full body or specific to the areas you request.
Reflexology known by the Chinese to be the ultimate body relaxation treatment, enjoy the effects of this soothing approach to whole body repair. As the specific pressure points on your feet are massaged, feel the stress and strain slip away.
Half Day and Full Day Rates:
The Highland House spa services are available at Half Day and Full Day rates. For these rates, you can receive any combination of the services above. Please allow sufficient time to complete the treatments requested. Each service is approximately 45-50 minutes with 10 minutes needed to prepare for the next service.
Prices subject to change at anytime.
Rates for Highland House
* Rates are weekly and include all Jamaican Taxes
* Winter Season or High Season, December 15 to April 15 (excluding Christmas and New Years weeks) 7 nights minimum
* Summer Season or Low Season, April 16 to December 14 (excluding Thanksgiving week) 5 night minimum
* Christmas week is defined as (Dec 20 to 27) or (Dec 21 to 28)
* New Years week is defined as (Dec 27-Jan3) or (Dec 28 to Jan 4)
* Thanksgiving is defined as Nov 20-27 (1 week minimum stay)
* Villa rates are weekly and can start on any day of week.
* Rates are quoted in United States Dollars (USD)
* 25% deposit confirms a reservation
* For Highland House: Minimum stay of 4 night required in low season Supplement of $35.00 pp/night will apply to each guest in excess of 12 (2 per room)limit.
Bedroom Room Configuration
Zen Room : King-size 4-poster cedar bed, spacious sitting area, television and VCR, 5 ceiling fans, sliding doors to lower lawn and view of the sea. En-suite bathroom, 2 basins, shower, 4'X8' linen-draped Roman tub.
Jamaica Suite: Best for children. 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.
Owner's Suite: 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.
Mahogany Suite: Queen-size bed, rich coral walls and mahogany trim, kilim rugs, television and VCR. French doors to view of lawns, woods and sea. En-suite bathroom. Shares covered terrace with Deco Suite.
Deco suite: Optional king-size or twin mahogany beds under mosquito netting in glamorous, colourful room. Television. En-suite bathroom and walk-in closet. Shares covered terrace with Mahogany Suite.
Bird Room: The Bird Room has a king bed which can be separted into two twin beds (has a mattress topper), 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.
Tryall Club Membership Inclusions
Tryall Membership offers first Rate facilities on its 2200 acre Resort
Conde Nast places Tryall Club on its Gold List as one of the best places to stay in the world.
* * Tryall's Golf Course measuring 6,221-yards, par 72 course is considered to be the finest in the Caribbean and is the pride of Jamaica. It attracts the game's leading players and prestigious international events including the Johnnie Walker World Championships, Mazda Champions, Jamaica Classic and Shell's Wonderful World of Golf. This world class golf course boast hillside and seaside fairways. In-house greens fees offered to the villa's guests.
* * Complimentary shuttles transport guests from the villa's front door to all locations within the resort
* * Large swimming pool at Great House
* * White sandy private beach
* * Waiter Service on beach, serving drinks/food from beach bar
* * Beauty salon, massages, reflexology treatments
* * Hobie Cat Sailing and Sunfish sailing are complimentary
* * Sea Kayaks which accommodate up to three people are also available at the beach.
* * Snorkels, masks and flippers are provided. Take a leisurely swim to the coral reef just 100 yards off this private beach
* * Tryall's watersport center can arrange for all your diving needs as well as opportunities for water-skiing and tubing. Fees may apply.
* * Gym for workout at Fitness Centre
* * Jogging trails
* * Complimentary internet room
* * Historic Great House with bar, boutiques, art gallery, fax facilities
* * Enjoy Afternoon Teas at the Great House
* * Great House Restaurant for continental and Jamaican dining if you wish to dine away from the villa, with its outdoor terrace.
* * Play tennis on 7 Nova Cushion courts, which are lit for night play.
* * 2 Brand New Clay Courts with 2 additional courts for a total of 9 tennis courts!
* * A well-stocked pro-shop, with an international pro, a highly-skilled team of teaching assistants and ball boys, holds regular clinics and hosts weekly tournaments.
* * Kids Club, keeping the kids happy. Children are entertained, cared for and close at hand. The Kids' Club offers daily activities which make full use of Tryall's amenities and the expansive grounds of the estate.
* * Friendly, caring and professional babysitters are available for hire for a few hours or full-time service
TRYALL CLUB, MONTEGO BAY- (HIGHLAND HOUSE villa is an 8 minute drive from the Tryall Club were you can enjoy these resort amenities!)
Tryall is a private club is one of Jamaica's premier resorts in Montego Bay. Amenities include tennis,18 hole championship golf course, beach, water sports, the excellent gym, the Kids Club, Great House afternoon tea and various special events.
The Tryall Club, Jamaica's premier private club, offers members and discerning guests the luxury and hospitality of a true villa lifestyle.
Set amid 2,200 lush acres, The Tryall Club provides all the ingredients necessary for an exquisite experience: world-renowned golf, private beachfront, exceptional cuisine, and the best views in Jamaica.
For players of any age, The Tryall Club offers the ultimate tennis experience. Tryall offers facilities of the highest quality, including four Classic Clay™ courts and five Nova-Cushion hard courts that have played host to numerous Davis Cup matches and an annual Legends event. Our large in-season tennis staff—24 pros, hitting partners, ball boys and others—provides exceptional service to guests in the classic Tryall tradition.
The 18-hole, 6836-yard, par 71 course, designed by Ralph Plummer, has been rated "among the most beautiful golf courses in the world." This tricky, wind-swept course offers stunning views, unique natural hazards and challenging greens. With the front nine holes bordering the Caribbean Sea and the back nine winding through verdant hillsides, Tryall offers stunningly diverse topography.
Enjoy the beach and non-motorized watersports at the Tryall Club
The 18-hole, 6836-yard, par 71 course, designed by Ralph Plummer, has been rated "among the most beautiful golf courses in the world." This tricky, wind-swept course offers stunning views, unique natural hazards and challenging greens. With the front nine holes bordering the Caribbean Sea and the back nine winding through verdant hillsides, Tryall offers stunningly diverse topography.
Children enjoy daily activities that make full use of Tryall's amenities and expansive grounds. Your children will love the Hummingbird Kids Club, offering complimentary daily activities for kids from 5 to 12 years old. Kids can also participate in various activities, including treasure hunts, talent shows, face-painting, beach Olympics and more. Toddlers (accompanied by baby sitters) and teens are also welcome to join in selected activities.!
Caribbean sea and tradewinds, the beauty of the Caribbean!
Tryall Club with Great Plantation House and Beach restaurant
Enjoy our sandy white beach at the Tryall Club. Sailing, kayaking, tubing, waterskiing, a water trampoline — all are available in the waters immediately off the shore of the Tryall Club. Just a short swim from the beach, a coral reef offers stunning underwater views for snorkelers.
Enjoy our 18 hole Championship course. Golf for adults and also, for the kids!
Enjoy tennis on our clay courts and hard tennis court - Day and lit for night play!
Exquisite cuisine served when and where you like—yet another example of the Tryall experience. Our dining options range from breakfast at the great House to intimate gazebo dinners with the Caribbean Sea and cool tropical breezes providing a romantic ambience. From Breakfast at the Great House (during season) or at the Beach Café (off season), to dinner on Seafood Night or Beach Barbecue Night on the Lawn with entertainment, or a quiet family dinner at the Gazebo (max of 12 persons required), our professional gourmet chefs offer a variety of tastes for the discerning palate, serving the finest and freshest meals in Jamaica. You'll have your choice from among a broad menu of West Indian or Continental favorites. Or, simply ask for a dish prepared especially for you.
Great House Restaurant and Great House Terrace Start your day with breakfast at the Great House, where you can enjoy service as unique as the view, from this historic architectural landmark. High tea, served daily at the Great House, remains a highlight for our visitors. For a memorable dining event, try dinner at the great house terrace – an elegant, candle-lit affair featuring international and Jamaican cuisine with beautiful views of the lights of Montego Bay. Later at the great house, enjoy night time at the bar – a lively gathering place for Tryall guests. The great house also hosts weekly events, including a cocktail party hosted by the club's management and members.

Getting There

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