Trip Planner

Villa Rentals (Please note holiday rates November-January are available upon request)
  • $1,075.00-$1,200.00 per night, (12 adult maximum, 4 nights minimum)
  • $75.00 per person for exclusive meet & greet airport to villa transfers, round trip
  • $75.00 per person, per day for chefs fresh breakfast, lunch and dinner
  • 15% gratuity, for high touch service shared amongst five full-time staff
  • Complimentary WiFi, Welcome Rum Punch, Tea, Coffee and a 24-hour on-site contact


While reservations can be taken less than a month in advance, it is recommended that you reserve the Highland House at least 6 to 9 months before you travel to ensure availability.
Please note: A deposit equal to 25% of the rental fee must be paid within 10 days of contract signing. The remainder of the rental fee, plus 15% staff gratuity and any transportation or meal plan purchases must be paid 60 days prior to arrival.

The meal service is a defining characteristic of the Highland House experience. Designed exclusively for the estate by two notable chefs, 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.

The Highland House features a special organic garden. You are encouraged to accompany the gardener to pick fresh vegetables for your meals. In addition to the plentiful garden, you’ll find trees with mangos, coconuts, bananas, plantains, avocados, and papayas to enjoy!

Meal Plan

3 Meals per day*
Iced tea and water
In-room coffee service
Fruit smoothies

*Explore the new house menu by clicking here


Age 13+ $75 per person per day
Under 13 $55 per person per day
*No charge for children 6 and under
Appetizers upon request at $10 per person per day
Unlimited Rum Punch at $25 per person per day
OR Appetizers and Unlimited Rum Punch at $28 per day (Value!)

Please note: Costs of sodas, alcoholic beverages, mixers, and snacks constitute an additional charge based on consumption. Guests are asked to select meals in advance and pre-pay for groceries. Staff must be informed of dietary restrictions at time of menu selection. We can cater to both vegan and vegetarian dietary requirements. Refunds of $10 for breakfast or lunch and $20 for dinner are given if meal is cancelled with 48-hour notice. We ask that you pre-select your menu choices as the garden is seasonal, and we may need to supplement the items necessary to deliver fresh fish and vegetables.


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.

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.

Half Day – 3.5 treatment hours $150
Full Day – 6 treatment hours $250


Airport Transfer

$70.00 round trip per person

Full-time Van & Driver

At your request, the Highland House coordinator can reserve a van/driver for you. Rather than renting a car or taking a taxi, a driver service is the most economical and reliable option in this region.

During your stay, you can have a driver and van available for all your transportation needs. An air-conditioned van can seat up to 10 or 25 passengers. One tank of petrol (gasoline) is complimentary for all full-time service.

Full-time van and driver – 12-Seater  Rate: $925.00

contact Highland House for more individualized rates.

Please note: Full-time service is offered for a minimum of 4 consecutive days. Trips beyond Negril and Ocho Rios incur an additional cost.

Per-Trip Service

If you choose not to reserve full-time service, the following rate applies:

$25 per hour with a 2-hour minimum


If you can bring yourself to leave the comfort of the Highland House, you’ll find there are all forms of adventures in Jamaica. Sun-soaked beaches with luminous turquoise waters are just 10 minutes away, as are resort golf courses, horseback riding tours, catamaran cruises, watersports, and more. You can pre-arrange your activities before you arrive with the help of the Highland House coordinator, or ask the butler to organize spontaneous activities.

Appleton Rum Distillery

Take a guided tour of the distillery and sample various rums. Combine with a visit to Y.S. Falls.

Black River Safari and Y.S. Falls Tour

Located on the south side of the island – a twenty-minute drive from the villa. Take boat ride up Black River to see crocodiles in their natural habitat. Visit spectacular and picturesque Y.S. Falls ($14.75 entrance fee).

Croydon in the Mountains

Tour a working coffee plantation and enjoy tasting samples.

Deep Sea Fishing and Sailing Charters

411′ Viking tournament-equipped sport fishing boat plus SunCat Catamaran for up to 60 guests with crew of 5. Snorkeling, sunset, and private party charters. Rates and Reservations: 876-995-2921 or page at 876-936-6207.

Duty-free Shopping

Montego Bay or Freeport (where cruise ships dock). Also, Half Moon Shopping Villa and Holiday Inn shopping arcade. Big craft markets in Montego Bay, Ocho Rios, and Negril. Dealing for the best price is expected.

Greenwood Great House

Built by the Barrettes of Wimpole Street in 1790 for entertaining. The “greatest” Great House in Jamaica. The finest antique museum in the Caribbean plus amazing view from the veranda of the curve in the earth’s surface. Well worth the trip to Falmouth. $10


Tryall Golf, Tennis, and Beach Club 876-956-5660
Half Moon Golf Club 876-953-2560
Wyndam Rose Hall Country Club 876-953-2650
Ironshore Golf Course 876-953-2800
Ritz Carlton 888-281-3778

Horseback Riding

Half Moon 876-953-2211
Rocky Point Stables (mountain riding) 876-953-2286
Good Hope Riding (jungle & waterfalls) 876-954-2289
Oasis Riding Stable (mountain riding) 876-953-3013
Martha Brae Rafting
Approximately 1 hr 15 min ride 18 miles east of Half Moon, 2 miles south of Falmouth.

Mayfield Falls

1 and half hr drive. Incredible hiking, waterfall, and ecology tour.

Massage/Spa Service

A full range of services available including full body massage, facials, reflexology, and body wraps, as well as manicures and pedicures.

Mountain Valley Rafting

Float downstream on a bamboo poled raft through Jamaica’s tropical countryside. Jitney tour of the area and lunch are optional.


1 hr 15 min drive. West of Montego Bay. 7 miles of white sand beach, clubs, restaurants, reggae, and beach bars. Totally casual. Watch the sunset from the infamous Rick’s Café. Cliff diving and snorkeling on Negril’s reefs.

Ocho Rios

90 min drive east of Montego Bay. See fabulous Dunn’s River Falls. Take swimsuits and sneakers and walk the falls with guides.

Pier 1

Funky and casual native waterfront bar. Cruise Montego Bay and party every Friday night ($25 per person cash bar). Opposite the craft market in town.


The staff will give you a list of restaurants should you wish to dine out. A good variety is available, from roadside jerk pork to elegant candlelight Continental cuisine.

Rockland Feeding Station

Reach out and touch Jamaica’s exotic Mango Hummingbird, Orange Quit, and Doctor Bird. Bird feeding daily at 3:30 in Anchovy (15 minute drive).

Rose Hall Great House

Legendary home of Annie Palmer (the White Witch) who ruled cruelly and died violently. An exciting tour of the home. Open 7 days/week $15

Round Hill Beach Party

Every Monday, beach barbecue buffet with Calypso band. Every Friday, Jamaica Night with Jamaican buffet plus steel band or reggae band plus Jamaican floorshow. $49 for dinner and music (beverages extra). Children under 12 get 50% discount. Reservations 876-956-7050.

Scuba Diving & Snorkeling

Captain’s waters sports at nearby Round Hill. Poseidon divers give lessons, equipment, and guidance to fish and coral 6′-120′ down plus cave, canyons, and sponges 150 yards off shore. Also, excellent diving at Tryall Beach Club, Half Moon, and on Negril’s reefs. For a special treat, call Ben Baker for a private scuba lesson in your own villa pool. He’ll take you out for a real dive when he has certified you after two or three lessons.

Sunset Cruise, Snorkeling, Fishing

Call Bertrand Sailly at Reading Reef to reserve sunset cruise in a powerboat or fishing trip including gear or boat tour of Negril or Marine Park. Max. of 8 passengers. Full day $600, half day $300. 876-952-5909

Timair Air Tour

See the grandeur of Jamaica’s mountains and coastline from the air. 876-952-2516 (day) or 876-952-8237 (evening).

Tryall Beach Party

Every Thursday (call to check availability). Beach barbecue and dancing, reggae music, entertainment, fun. $35 for adults, $17.50 for children under 12; no charge for children 4 and under. Add 10% service charge. Drinks additional. Call one day in advance for reservations. 876-956-5660

Water Sports Rentals and Sunset Cruises

Tryall 876-956-5660
Half Moon 876-953-2211

Other useful information

The Highland House Villa
Kingsgate Road, Reading P.O.
Montego Bay, Jamaica
Telephone: 876-605-1377

Check-in and Check-out Times

Check-in time is 1:00 PM. Check-out time is 11:00 AM on departure days unless no other guests are scheduled to arrive that day. A Highland House representative can advise you.

Travel Documents

Tourism is Jamaica’s leading industry, so reserve flights early. Your destination is Montego Bay. Air Jamaica, Air Canada, Delta, Northwest, and USAir are major carriers. British Airways flies non-stop from London. Several charters operate from the East Coast, the Midwest, and Europe. Proof of citizenship in the form of a passport is required.


Jamaica enjoys typical Caribbean weather with temperatures in the 80′s and 90′s by day and in the 70′s by night. Winter to summer variance is only 10 degrees. You may need a sweater during the winter evenings.


Jamaican dollars, British pounds, US dollars, and traveler’s checks are accepted island-wide. Commercial establishments accept credit cards. The current conversion rate is approximately Jamaican $44.00 = US $1.00.

Air Conditioning & Electricity

All suites have air conditioning. Electricity is essentially the same as US: 110 volts, 50 cycles (US is 60 cycles). Converters are not necessary for US appliances.

Telephone – Overseas Calls

Highland House offers FREE long distance dialing from HH to US, Canada and Great Britain. Most cellular phones will work in Jamaica, but be prepared to pay roaming charges.

Satellite TV, DVD & Surround-Sound Stereo

From the terrace and numerous areas around the pool, you can enjoy the surround-sound stereo system. Bring your favorite CDs to relax to.

Internet Access

FREE internet access.

To ensure the availability of services, please contact us with the following at your earliest convenience:

  • Number of guests (and their ages) in your party
  • Number of meal plans* per day and any dietary restrictions
  • Dinner selections for group (breakfast and lunch are chef’s choice)
  • Spa service* requests – number of full days, half days, or individual sessions
  • Transportation* times and dates, whether full-time driver or air transfers only
  • Names and flight arrivals/departures for all guests
  • Pre-stock requests* – such as snacks, bottled water, soda, alcoholic beverages, and special requests
  • Prepayment of items with asterisks

With your information in hand, the Highland House coordinator will inform the cook of your meal selections, book your air transfers, and pre-arrange activities and special requests. For group trips to the Highland House, we ask that one person from your group be in charge of gathering the payments and information from the rest of the party.

*These items require prepayment, but you always have the ability to add meals, activities, and supplies as needed.