- Villa by Name
Testimonial
You can read all you need to in our brochures and these web pages, but the real stories are told by our guests... read more
Jamaica’s Most Charming Villas
- Highland House.
*Jamaican Treasures Best Service Award 2005
| Owned by Dorothy and Oscar Hammerstein in the 1960's and featured in Island Home magazine. Deluxe 6 bedroom, 6 ensuite bathrooms, a wonderful and private compound with bedrooms under four separate roofs. Large 7000sq ft home set on over 17 wonderful hillside acres in Montego Bay. Attention to detail, professional interior designs, In-House Spa Service, personal concierge, surround sound stereo system, Satellite TV service, VCR. Professional long serving staff, wonderful service, very friendly. Only 12 miles from the airport. Sleeps 12 guests. |
3 Bedrooms, Pool, Views, Membership - Tryall, Montego Bay |
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| 3 bedroom, 3 bathroom located in the famous Tryall Club estate. Ideal for families. Large covered open air patio over looking swimming pool. Lovely villa with spectacular views of Tryall’s golf fairways and the blue azures of the Caribbean Sea. Complimentary Tryall membership gives access to resort’s beach club, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts, and world class golf and much more. Only 25 minutes from the airport. Sleeps 6 guests. |
3Bedrooms, Pool, Jacuzzi tub, Views, Membership - Montego Bay |
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| 3 bedrooms, spectacular views of Caribbean Sea and Montego Bay, all bedrooms air conditioned, Jacuzzi tub upstairs. Master bedroom upstairs and 2 bedrooms downstairs open onto pool terrace. Charming home, spacious wrap around veranda with views. Charming villa with the prestigious Round Hill membership, only 5 minutes away from Round Hill resort facilities. 25 minutes from the airport. Sleeps 6 guests. |
3 Bedrooms, Oceanfront, Pool, Membership - Tryall, Montego Bay |
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| Lovely 3 bedroom, 3 bathroom absolute waterfront property. Prime location, Tryall’s ocean frontage. Children friendly, very comfortably and wonderful decorations for this tropical island getaway. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 6 guests. |
5 Bedrooms, Pool, Membership - Montego Bay |
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| 5 bedrooms, 5 bathrooms, remarkable views of Caribbean Sea, 5000 sq. ft. home, immaculate home, wonderful interior designs. 5 minutes drive to Round Hill Resort to enjoy your complimentary membership. Large lawn areas, great for kids, manicured lawns, inviting pool, only 25 minutes from the airport. Sleeps 10 guests. |
4 Bedrooms, Pool, Gardens, Views, Membership - Tryall, Montego Bay |
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| This villa has one of the best views in the whole of Tryall. 4 bedrooms, 4 bathrooms, large expansive swimming pool, colourful tropical flowers, manicured gardens, unique Jamaican cut stone architecture, wonderful features. Wonderful cedar wooden floors, spacious bar area and lounge area on top floor, main house has 2 master bedrooms and two spacious bedrooms located in private cottage next to pool. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts, and world class golf. 25 minutes from airport. Sleeps 8 guests. |
2+4 Cottages, Most charming, Beachfront, Gazebo, Pool - Discovery Bay |
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| These cottages comprise of a 2 bedroom and 4 bedroom cottage on absolute waterfront prime property in Discovery Bay. Own private white sandy beach, swimming pool, kayaks, air-conditioned bedrooms, BBQ, beach chairs, waterfront gazebo. Cottages share massive lawn area, pool , beach, volleyball, badminton area. Full staff to make this a real holiday. Perfect for families or casual group reunions. Sleeps between 4 to 15 guests. 60 minutes from the airport. |
2 Bedrooms, Pool, Garden, Membership - Tryall, Montego Bay |
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| This is a private enchanting villa, located beside the 17th fairway of the famous Tryall Club and is across the street from the Caribbean Sea waterfront. Lovely setting, with swimming pool, only 2 bedrooms, sleeps 4 people. Walking distance to Tryall’s beach resort. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 4 guests. Wonderful honeymoon cottage. |
4 Bedrooms, Oceanfront, Pool, Gazebo, Estate Amenities - Ocho Rios |
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| Located in Ocho Rios, 4 bedroom, 4 bathroom, waterfont property situated on 1 ½ acres of the famous Prospect Estate. Fresh interior designs, very comfortable villa, close to all Ocho Rios sights and amenities. Large swimming pool and gazebo, sunning deck set in rocks, access to clear blue waters. Guests enjoy the free use of the Estate’s tennis court, 18 hole miniature golf, the popular Prospect Plantation jitney tour and horse back riding tours, preferential green fees at Sandals. 1 ½ hours from the airport. Sleeps 8 guests. |
5 Bedrooms, Oceanfront, Pool, Membership - Tryall, Montego Bay |
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| 5 bedroom, 5 bathroom, absolute waterfront location in the famous Tryall Club resort. Large swimming pool at waters edge, interiors are very comfortable, high quality furnishings, large sofas, thick poolside lounge chairs, elegantly decorated to suite the tropical atmosphere. Children friendly, all guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 10 guests. |
4 Bedrooms, Pool, Views, Membership - Tryall, Montego Bay |
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| Beautifully furnished 4 bedroom, 4 bathroom villa in the world famous Tryall Club. Spectacular views, large private pool, covered poolside bar and lounge, staff of 5, air conditioned bedrooms, children friendly, internet access. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface court and world class golf. 25 minutes from airport. Sleeps 8 guests. |
4 Bedrooms, Pool, Views, Estate Amenities - Ocho Rios |
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| 4 bedroom, 4 bathroom, wonderful pool with spacious sundeck and views of Caribbean sea, steps to jetty with walk out access to clear blue waters. Located in Ocho Rios, close to all sights and amenities. Situated on the historically significant Prospect Plantation, 980 acre estate in Ocho Rios. Guests enjoy the free use of the Estate’s tennis court, 18 hole miniature golf, the popular Prospect Plantation jitney tour and horse back riding tours, preferential green fees at Sandals golf and country club. 1 ½ hours from airport. Sleeps 8 guests. |
Bedrooms: 4, Pool, Views - Montego Bay |
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| Located within the prestigious Round Hill estate,
this wonderful 4 bedroom, 4 bathroom cottage has spectacular
ocean views. The staff here needs special mention, with over
20 years of experience, the butler and senior housekeeper
runs this house like a charm. This wonderful villa is a favorite
for repeat guests. The staff here is special, all long serving
and professional, making a truly relaxing holiday. Complimentary
transport to Round Hill beach Club and complimentary membership. |
3 Bedrooms, Pool, Views, Membership - Tryall, Montego Bay |
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| Linga Longer is a most charming 3 bedroom villa within the famous Tryall Club Resort estate. It is located on a hillside which lends itself to the most beautiful views of the 13th green and blue azures of the wonderful Caribbean ocean. Unique to this villa is the entrance is a wonderful enclosed brick courtyard, with a sparkling blue swimming pool. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 15 minutes from airport. Sleeps 6 guests. |
4 Bedrooms, Pool, Views, Membership - Tryall, Montego Bay |
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| Charming 4 bedroom, 4 bathroom cottage, wonderful views to the famous Tryall golf course, backing onto the 9th green. Unique circular and octagonal design takes full advantage of views of hills, fairway greens and wonderful Caribbean sea views from all different sides. The main focal point is this wonderful blue sparkling circular pool which is at the center of this villa, surrounded with terracotta brickwork. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. |
Bedrooms: 5, Bathrooms: 5, Pool, Gazebo, Views, Garden, Membership - Tryall, Montego Bay |
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| Deluxe 5 bedroom 5 ensuite bathrooms, brand new renovations end 2004 has made a luxurious bedroom and bathroom, state of the art kitchen, poolside gazebo. Spectacular hillside and breathtaking Caribbean Sea views. Lovely garden entrance courtyard, large infinity pool, the perfect hideaway. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 10 guests. |
Bedrooms: 2+2 , Private beach, Natural saltwater pool, Membership - Tryall, Montego Bay |
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| The most charming beach house sent on 2 acres of prime waterfront property between the 17th tee and the Caribbean ocean. Features a totally private, white-sand beach, the main house has 2 charming bedrooms, and a perfect hideaway guest cottage has 2 additional bedrooms. Natural saltwater swimming pool at waters edge, great position for snorkelling. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. A true gem. |
4 Bedrooms, Pool, Gazebo, Garden, Views, Membership - Tryall, Montego Bay |
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| Waterfront location, 4 bedroom, 4 bathroom, magnificent views of Blue Caribbean Sea. Upon entering Reef House, you walk over a lovely bridge which goes over a wonderful lily pond. Wonderful circular pool, and seaside gazebo. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. |
4 Bedrooms, Pool, Views, Membership - Tryall, Montego Bay |
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| One of our favourite cottages, 4 bedroom, 4 bathroom, entrance courtyard with wonderful fountain to greet guests. Large swimming pool, expansive lawn area graced with tall palm, seaviews, 18th fairway views. Main house has 3 bedrooms, new honeymoon cottage most charming and wonderful interior decorations throughout. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. |
4 Bedrooms, Pool, Garden, Membership - Tryall, Montego Bay |
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| Most charming 4 bedroom, 4 bathroom set in 2 lovely cottages within the famous Tryall estate. Newly decorated villa, all soft furnishings are wonderful colours. Hillside location, magnificent views, heated large oval swimming pool. Manicured gardens, long serving staff at this villa. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. |
4 Bedrooms, Beachfront, Pool, Gazebo - Discovery Bay |
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| Most charming cottage located on “Millionaires Row” in the picturesque Discovery Bay. 4 bedrooms, 4 en-suite bathrooms, all bedrooms air-conditioned. Small man-made beach, 16-jet plunge pool, snorkelling equipment, sunning platform and complimentary sea kayaks. Romantic seaside gazebo, most comfortable home, children friendly, full staff to serve. Golf, tennis and more water sports nearby. Most wonderful and relaxing villa with a 60’ veranda with full views of the beautiful bay. 60 minutes from the airport. Sleeps 8 guests. |
3 Bedrooms, Oceanfront, Pool, Garden, Views, Membership - Tryall, Montego Bay |
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| Charming 3 bedroom, 3 bathroom waterfront villa in the famous Tryall Club estate. Breathtaking views, swimming pool, lovely garden and fountain courtyard. Most comfortable villa with beautiful furnishings throughout. A most welcoming tropical home. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 6 guests. |
5 Bedrooms, Private beach,Gazebo, Tennis court - Discovery Bay |
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| Beautiful 5 bedroom, 5 bathroom waterfront villa in the picturesque Discovery Bay. Wonderful villa with very comfortable interior furnishings throughout. 3 bedrooms located in main house, 2 bedrooms in casual cottage, all bedrooms air-conditioned, own private white sandy beach, own private tennis court lighted for night play, sea kayaks, large lawn for kids running space, waterfront gazebo, long serving staff. Great for families. 60 minutes from the airport, sleeps up to 10 guests. |
4 Bedrooms, Oceanfront, Pool, Jacuzzi, Membership - Montego Bay |
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| Deluxe 4 bedroom, 4 bathroom cottage, located within the famous Round Hill resort, complimentary membership for guests, high rate of returning guests, absolute waterfront villa, rolling lawns, swimming pool, hot tub Jacuzzi, open air outdoor shower, internet connection, only 25 minutes from the airport. Sleeps 8 guests. |
3 Bedrooms, Beachfront, Pool, Tennis court - Montego Bay |
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| Absolute beachfront property with 3 bedrooms, 3 bathrooms. Shared tennis court with neighbouring Tranquillity villa, all bedrooms face the sea and are air conditioned. Wonderful decorations throughout, unique octagonal rooms connected by long furnished veranda. Very casual and comfortable villa, very high rate of returning guests. Only 20 minutes from the airport. Sleeps 6 guests. |
4 Bedrooms, Pool, Gardens, Estate Amenities - Ocho Rios |
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| 4 bedroom, 4 bathroom waterfront villa located in pretty Ocho Rios. Swimming pool, poolside BBQ, lush garden setting, swim and snorkel in the clear crystal waters of the Caribbean Sea. Situated on the historically significant Prospect Plantation, 980 acre estate. Fully staffed, included airport transfers. Guests enjoy the free use of the Estate’s tennis court, 18 hole miniature golf, the popular Prospect Plantation jitney tour and horse back riding tours, preferential green fees at Sandals golf and country club. |
4 Bedrooms, Private beach, Pool, Membership - Tryall Montego Bay |
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| Lovely 4 bedroom, 4 bathroom waterfront cottage in the beautiful Tryall Club estate. Breathtaking setting, own private sandy beach, snorkel out the reef ,just across the lane is the driving range and the first tee, comfortably furnished with Jamaican wicker in the living room to reflect the true tropical style, wonderful swimming pool around manicured lawns. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 4 guests. |
3 Bedrooms, Private beach, Pool, Membership - Tryall, Montego Bay |
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| Charming 3 bedroom, 3 bathroom waterfront villa. Located in the famous Tryall Club estate, brand new renovations, swimming pool at waters edge, outlook over private beach, great for snorkelling. Perfect place for breathtaking sunsets. All guests entitled to complimentary Tryall Membership which gives access to resort’s beach club, tennis, fitness room, state of the art tennis center with 4 Classic clay and 5 Nova Cushion surface courts and world class golf. 25 minutes from airport. Sleeps 8 guests. |
4 Bedrooms, Private beach, Pool, Tennis court, Membership - Montego Bay |
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| Beautiful 4 bedroom, 4 bathroom waterfront villa. Main house has 3 bedrooms, and Beach Cottage has and additional bedroom, with a smaller 5th bedroom suitable for children. Own tennis court shared with neighbouring Serenity villa, private pool, 100 yards of it's own white sandy beach. Truly beautiful beach house, wonderful furnishings, very children friendly, high rate of returning guests. Sea kayaks, exercise and fitness equipment, stair stepper, bench press, dumbbell, free weights, basketball set up on tennis court. Only 20 minutes from the airport. Sleeps up to 10 guests. |
4 Bedrooms, Oceanfront, Membership - Montego Bay |
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| 4 air conditioned bedrooms, 4 bathrooms, absolute waterfront location. Wonderful restored 18th Century home, great for families. 3 separate cottages, beautiful furnishings, high quality interiors, wooden floors, rich mahogany furniture, lovely children’s cottage for kids, full staff, sea kayaks. Complimentary membership to the famous Round Hill Beach Club only 5 minutes away. Wharf House is located only 20 minutes from the airport. Sleeps up to 8 guests, great for families. |





























