These spectacular over-the-water bungalows offer an unmatched connection to the Caribbean Sea and deliver complete immersion with fine turquoise waters and rich marine life below.
Our most nature-integrated villa, this home has two bedroom suites on four beachfront acres purchased from the Jamaican government. Dense tropical foliage has been fully-preserved, so guests enjoy full sun and also shaded seating under “tree umbrellas” on the lovely white sand Bluefields Beach
Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms. Built many years earlier, it was purchased in 1986 and extensively remodeled and personalized. This is when its luxurious cliffside plunge pool with underwater seats was added—the perfect place for soaking up sun
High on the hillside of Copperwood Ridge and almost hidden amongst its exceptionally pretty gardens and surrounded by an aura of blissful calm is a uniquely special house called Serenity
This updated three bedroom property, is an elegant, family- friendly villa that sits right on the water’s edge, with a unique private pool deck overlooking the water and beautiful views of Montego Bay in the distance
Providence House was completed in 2008, and is located on the former landing site of the area’s deep-sea night fishermen. It is rumored that in 1793, Captain William Bligh (of Mutiny on the Bounty fame) arrived to this spot from Tahiti aboard the HMS Providence, bringing with him the prized cash crop breadfruit that has since become a popular local food and a valuable export
Architect-designed and lauded as a prized jewel of our luxury Caribbean resorts, this distinctive home was completed in 1991. In building The Hermitage, major emphasis was put on using local workers and Jamaican materials (stone, marble, mahogany, cedar) to reproduce features of authentic and traditional Jamaican homes
Casuarina is a hidden gem and one of the loveliest villas. The ocean views are breathtaking whilst inside there is a magical charm created by a very clever combination of flower-filled gardens, furniture designed for total comfort and stunning contemporary bathrooms.
Eureka is the closest anyone is ever likely to get to stay in a Jamaican Great House that is furnished of the period and opportunities such as this do not come along very often. This utterly delightful home stands amidst very pretty gardens and commands a clear unobstructed view of the sea and golf course
From its high perch atop Barnes Hill, this luxury villa commands a truly breathtaking view over emerald lawns, an infinity pool and the broad expanse of Tryall Club’s legendary golf course. To complete this magical picture are infinite views of the turquoise Caribbean Sea.
Reef House is the embodiment of oceanfront cottage living. This gorgeous home brings the outside in, bathing the rooms with soft natural light and the irresistible blues of the ocean beyond.
Ma' Moura is a wonderful villa which is open and spacious with a sparkling circular swimming pool as the focal point for entertaining and relaxing. This villa is of an octagonal design takes full advantage of the view on all sides. The views of the golf greens are superb from this villa with a rolling manicured lawn leading down to the 14th green as your back yard.
Bluebird is a four-bedroom villa overlooking a magnificent tropical garden and the glittering panorama of the Caribbean Sea. A spacious, living room lifts your spirit with soft furnishings in up-tempo hues of blue and yellow accented with crisp white.
Yellowbird is a spacious and cheerfully tropical deluxe villa that celebrates the joys of island living with traditional Jamaican design and spaces that open on every side to embrace views of the sea and the lush Tryall property
One of just a handful of Tryall villas which has its own private beach (depending upon the tide), Tradewinds On The Sea has the most spectacular sea views with an interior style that is the epitome of modern beachfront living.
Located right on the oceanfront at the western end of the Club, Aqua Bay redefines the concept of ocean style. Reflecting the ambiance of the sea throughout, this handsome villa boasts not only a splendid zero-edge heated pool with spa but two swimming holes on the coastal strip fed with sea water and a white sand elevated beach.
Little Hill was built in 1959 by the acclaimed architect Robert Hartley. It is built in the classic West Indies style around a 30 foot diameter swimming pool with extensive covered terraces throughout.
Mullion Cove set the tone and is the original prototype for the Bluefields Bay villas helping them become one of the top luxury resorts in the caribbean. The oldest of the collection, its history was easy to adapt for truly special holiday experiences.
A brand new addition to the exclusive Tryall Club, Sea Salt is one of the most welcoming private homes that grace the northern coast of this Caribbean paradise. Inside, you'll find classic Jamaican architecture and 7,700 ft² of living, dining and entertaining space. Outside, you're surrounded by 5.4 private acres, meticulously landscaped with native trees and indigenous plants.
Point of View is a truly spectacular deluxe villa perched on the top of Barnes Hill and located within the famous Tryall estate. This villa boasts breathtaking views of the Caribbean Sea from every point. The wonderful spacious veranda is a lovely focus point for relaxing, entertaining and casual dining.
Overlook is one of Tryall's newest additions to their collection of luxury villas in Montego Bay. With spectacular views of the Caribbean Sea and Tryall's famous golf course, Overlook villa lives up to its name with memorizing views. There are 5 wonderful bedrooms all with air conditioning for comfort.
Bougainvillea House is one of Tryall’s newest villas which is quickly apparent in the unsurpassed luxury it provides. Designed by one of Jamaica’s best known architects, it is built in classic Caribbean Georgian style but discreetly includes every 21st century luxury. It covers more than 8,000 square feet and sits in a panoramic location with 180 degree sea views.
Among the newest Premier villas at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool, Infinity is a vacationer’s paradise for golf and tennis enthusiasts, spa weeks, family reunions or merely relaxing into the good life for a week or more.
Elysian Plain is a waterfront villa which has a wonderful majestic, tall palm tree which guards the entrance of this villa. The unique feature of this villa is its location which sits literally at the edge of the clear, blue Caribbean Sea. The views from here are spectacular. "Elysian Plain" is aptly named after the resting place of the Greek Gods.
Luxury living is all about the details. Pineapple House has undergone a complete renovation, and it is prepared to please the most discriminating vacationers that appreciate luxury living.
This outstanding villa features Jamaican influenced architecture and furnishings with a wonderful collection of original paintings by well-known Jamaican artists such as Errol Allen, Messam, and Jeffrey Samuels. Hand-knotted Persian rugs and Jamaican grass rugs add a flourish to the floors
With a breathtaking setting, Villa Lolita is an elegant sanctuary and one of the finest villas in Jamaica. The villa features exceptional suites that offer optimum privacy with sensational views and meticulous attention to detail.
Offering what is undoubtedly the most magnificent ocean view in Tryall from a commanding position atop Garden Hill; Quinntessential is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish result in the epitome of sophisticated living without compromise.
This Villa, formerly Mahogany Hill, has the best views imaginable. I wanted to create, in some special way, the wonderful experiences I had had on the Island of Bali. Renowned for its beauty and tranquility.
Trinity's exquisitely appointed great room opens out to the top patio area where the lap pool is located. There is a formal dining room for elegant candlelit dinners, complete with a beautiful custom made table. For more casual dining options, Trinity has a terrace dining table, as well as a covered gazebo that over looks the dramatic waterfalls.
This is without doubt the finest oceanfront location at Tryall. If a private beach, the choice of two pools, a spa, extensive gardens and rooms that open to the sight and sound of the waves are top of your list then Stella by the Sea ticks all the boxes.
Villa Stella offers views of the Caribbean Sea and the Tryall Club estate from its two levels of spacious terraces. Villa Stella is situated on the brow of Copperwood Ridge. It is an easy walk to Tryall’s world class tennis courts, its gym, spa and other amenities, and a 3-minute ride by the villa’s complimentary golf cart to the hampionship Tryall Golf course and private beach.
Bumper's Nest encapsulates all that is synonymous with elegant Caribbean living with its lavish master cottage, handsome interiors and stunning views. From a three acre garden, at the peak of Mahogany Hill, Bumper's Nest takes full advantage of views of the Caribbean Sea
Harmony lives here…the house keeps you in touch with the surrounding elements in such subtle ways that you wonder why you feel so good . A spacious verandah waits to accommodate your drifting moods and a large green cushion of a lawn extends down to your own private beach cove. Here, you can decide whether to launch off in to the crystal blue seas using the kayaks perched by your side, or just melt gently into the warm Caribbean sea
This authentic home sits on the Caribbean with wraparound natural vistas of mountains and sea. Most distinctive, San Michele has a private island reached by footbridge where you can spend countless hours truly “on” the sea. After days of water sports, excursions, relaxation, and delicious repasts to your specifications, fall asleep to sea sounds from an authentic Jamaican four-poster canopy bed.
This magnificent villa is located on Mahogany Drive with the entrance driveway on Ocean View Drive. Constructed to the highest of standards and quality and with lovely sea views, Jubilation sits surrounded by a mature, beautifully landscaped garden that has become the favourite habitat of birds.
Rising from the hills, the seven rooftops of the Luxurious Highland Estate cover over 7,000 square feet. With six bedroom suites, the estate can accommodate up to 12 guests for overnight stays and larger parties for special events. Neighboring villas are available for additional overnight guests.
Keela Wee in Jamaica is one of the most beautiful vacation rentals you can experience. The true sounds and feelings of the Caribbean, with a full staff serving you delicate creations every day.
Following Seas is a one-of-a-kind vacation hideaway offering the ultimate in luxury, comfort and breathtaking décor. Following Seas' casual elegance seamlessly balances original artwork with classic Jamaican architecture
Wheel House combinines all the attributes of Caribbean living with privacy and seclusion. The open floor plan and indoor garden embraces the mountain breezes whilst celebrating fabulous ocean views.
Oceans 8 in Jamaica, this six (6) bedroom villa enjoys 300 feet of waterfront. With panoramic views of the Caribbean Sea and the city lights of Montego Bay in the distance, this brand new villa created a league of its own.
Windward is aptly named for the continuous cross current of trade winds that traverse the property. This graceful 6 bedroom home has the most spectacular 180 degree views from every room and from both levels
Rose Cottage sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in the old traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia, Jamaica and Europe…it is both elegant and comfortable and meant to be enjoyed.
Frankfort is a paradigm of 21st Century laid-back elegance. A brilliant half million dollar renovation introduced Italian Travertine floors, chic and comfortable sitting areas in crisp white fabrics, and stunning Euro-style modern bedrooms with all new en-suite bathrooms and glass-wall showers
Welcome to Flower Hill, one of Montego Bay’s most luxurious vacation home rentals. The Flower Hill villa sits on four and a half expansive acres of fragrant flower gardens and lush, verdant landscapes
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water. The architecture is superb.
Sundance is located on Mahogany Drive with magnificent views across vast sweeping lawns to the sea in the distance. The villa offers a level of comfort that is sumptuous and no expense has been spared in creating a residential masterpiece that will hold immense appeal for families as well as groups of adults.
At Amanoka the best of the Caribbean beauty and hospitality abounds. Within the villa’s walled compound, colors bursts from the tropical garden filled with exotic orchids and sensuous lily ponds.
For years Rose Hall Villas have played "home away from home" for many discerning clients. These 28-individual villas with private swimming pools, provide the ultimate Caribbean style escape. For the ultimate in luxury, we invite you to discover one of our Royal Villas
With one of the most panoramic views in all of The Tryall Club and a meticulous attention to detail and design, guests staying at the 7-bedroom Hummingbird House are often so captivated that they book it again before completing their current vacation
On Jamaica’s northern coast, just west of Montego Bay, The Tryall Club boasts some of the Island’s most prestigious luxury villas, resort amenities, and amazing ocean views. From its elevated perch, villa Dragonfly captures panoramic vistas of the lush green hillside and endless ocean
Twin Palms with its 60 mile ocean panorama is a house that is testament to the creativity and craftsmanship of Jamaica, whether it is the fine mahogany furniture, handsome doors, fanlights and ceilings or intricate metalwork in the form of light fittings, ornamental gates and sculpture.
Whispering Waters is an elegant, 12,000 square foot, two storey home. It is the ultimate in comfort and style with seven air-conditioned bedrooms with en-suite bathrooms that is beautifully decorated to the highest standards.
From its splendid location 300 ft above sea level, this luxurious 7 bedroom villa offers bewitching, unobstructed views of the ocean, its own private spa and Turkish bath, a putting green and a cinema.
Built in the traditional Caribbean style, Phoenix features a fabulous extremely private location on the sea with two private sand beaches and extensive seafront verandas that take full advantage of the splendid ocean views and ever present trade winds.
Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.
Silent Waters Villa Rental is a superb location for a family reunion, corporate retreat, destination wedding (seating 54 guests) or just a small group of friends seeking a most unusual holiday experience. Nestled in the hills of Jamaica, overlooking pristine forests and the spectacular turquoise waters of Montego Bay sits a truly remarkable private Jamaica resort property .... an enchanting heaven.
This luxurious fully staffed Villa is situated in Mammee Bay Estate, Ocho Rios and boasts a glistening white sand beach with 150 feet of its own beach frontage. The Villa can be rented in a five bedroom or seven bedroom configuration; which would includes the two bedroom cottage just steps away from the main house on the property.
You’ll see at once how Greatview got its name. An easy 10-minute drive from Montego Bay’s international airport, you'll find this oasis of beautiful gardens with spectacular ocean and mountain views. Both secluded and handy to golf, sailing, beach, horseback riding and other adventures, Greatview villa offers luxury accommodation and fine cuisine.
Sugar Hill Villa in Montego Bay is a stunning 8- bedroom, luxury island home privately perched atop a lush 3-acre property overlooking the glittering Caribbean Sea and the historic Tryall Club estate.
Promiseas Jamaica luxury vacation rental is above the rest. Designed to inspire relaxation with it's stunning contemporary feel set on a backdrop of pure bliss. The inviting open layout and windows that let the natural light into almost every room flooding it with warmth and a feeling of Zen. Discover Jamaica's newest luxury villa experience.
Hanover Grange in Montego Bay has become one of the highest profile, privately owned villas in the Caribbean, welcoming a succession of international celebrities, politicians and business leaders as guests.
Villa Amana in Montego Bay, Built in a striking colonial style with white-rendered walls, the villa is on two levels offering large rooms and a backdrop of tropical hillside forest. To the front, the commanding ocean view is truly spectacular and because of the elevation, at certain times of the day the curvature of the earth can be seen.
Golden Clouds villa is a luxurious 12-suite estate situated in a park-like 7-acre setting. It is a spectacular oceanfront villa located on Jamaica's fabled North Coast in the picturesque village of Oracabessa.
Jamaica boasts some of the best beaches and friendly residents that you will ever find. Not only is Jamaica considered a treat to visit but affordability is also a great part of why Jamaica stays on the map for vacations. Most people love the idea of traveling to the Caribbean and finding that right mix of sun and fun, so why not make it a Jamaica Holiday this year.
When you visit Jamaica, the best places are Kingston for those who want to go back in time and see the way Jamaica started out, Montego Bay for it’s nightlife and culture and amazing strips, Negril for its family friendly atmosphere, beaches, and lovely skyline, Ocho Rios for the waterfalls which people love to see, Port Antonio which draws the rich and famous to its magical coasts, and the South Coast for the local hotspots and great sunsets.
Some of the beaches include, Seven Mile Beach, Doctors Cave in Montego Bay, Aquasol, James Bond in Ocho Rios, Duns River Falls, Treasure Beach on the South Coast, Frenchman’s Cove in Port Antonio, and the Blue Lagoon.
No matter when you travel remember the climate changes in late May and we hit Rainy Season. So, traveling between November and early May are great choices. You can find some great deals during the summertime however, so check back often. Those traveling internationally, we highly recommend you take out Traveler’s Insurance, as these are by owner vacation rentals.
Jamaica offers holiday homes from beachfront to Oceanside, these homes are great for families traveling together and wanting to explore somewhere different, there are great resorts and homes throughout Jamaica.