Featured Homes
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.
Skyline is a one-bedroom luxury condo rental with views of the golf course and sea at The Tryall Club in Montego Bay, Jamaica. From the crest of the hill, at the heart of the Tryall property, adjacent to elegant 18th century Georgian Great House, Stella Marina looks over a sweeping panorama of lush forestry, blue seas and the picturesque Tryall fairways.
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.
Tryall’s only two-bedroom vacation rental, Little Palm, lives large nestled amidst an acre of lush garden on the 17th fairway and a short walk or quick golf car ride to the 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
Jamaican Me Happy is a lovely vacation rental in Tryall Club, Jamaica, for those looking for a great space to retreat to with ocean views.
Wag Water Villa is a beautiful villa in Ocho Rios Jamaica, set in a lush and tropical estate which has resort amenities and is a 5 star retreat for all who arrive.
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
Villa De-Luxe Paradise is a new addition to dreamexoticrentals luxury portfolio, curating the most incredible villas that offer an epic spin on luxury vacation rentals.
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
Somewhere Villa is an ocean view lovely cottage-style vacation rental in Ocho Rios Jamaica with amazing ambiance with resort like setting.
Casuarina is a hidden gem vacation rental within a wonderful golf resort in Jamaica and one of the loveliest villas at Tryall Club.
Frangipani in Ocho Rios Jamaica is a beautiful rental villa with ocean views great for families looking for both privacy and resort amenities.
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.
Villa Cielo in Tryall Jamaica is private and secluded vacation rental with the most magnificent ocean views from its hilltop setting.
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.
Sunrise is a classical beach cottage with an enviable oceanfront location and its own private sandy beach. The lovely laid-back atmosphere is just perfect for such a magical location.
Fairwinds offers rustic charm, amazing views, lovely gardens and two peaceful fresh water lily ponds with goldfish.
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.
Surrounded by a lovely garden and with a super view of the cobalt ocean, Blue Bird is a Tryall vacation rental that epitomizes living in the tropics.
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
In Arthurian legend, Avalon is where King Arthur’s sword Excalibur was forged and where he was taken to recover from his wounds after the battle of Camlann
From its lofty vantage point, No le Hace has fabulous unobstructed ocean views and an ambiance that is delightfully Jamaican.
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.
Located just short walk from the beach is Olive Branch Villa, a lovely vacation rental in St. Mary, Jamaica. This serene property sits on beautifully landscaped grounds boasting a panoramic view of the Caribbean Sea’s coastline, with cool hills hugging the rear of the villa.
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.
Point of View is a truly spectacular deluxe villa perched on the top of Barnes Hill and located within the famous Tryall estate.
Villa Overlook is an exceptional home with a perfect location offering commanding views and proximity to the many facilities of the Tryall Club. It is ideally suited to both families and groups of friends who seek optimum levels of hospitality.
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.
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
The Elysian Plain in Montego bay is a luxury vacation rental and sits literally at the edge of the clear blue Caribbean Sea, in Jamaica.
If you enjoy off-the-beaten-track adventures that transport you to another time and place, then this villa escape is your match made in heaven.
Villa Lido luxury vacation rental is a fabulous contemporary beach house situated right on the white sand, half-moon beach at Old Fort Bay.
Discover this light-filled haven of tranquility, nestled in the hills above Half Moon Bay - while easily accessible to bustling Montego Bay and its international airport.
Sunset is a beautiful five-bedroom villa that sits on the edge of the Caribbean Sea with a private beach offering the perfect escape for all those who love waterside living.
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.
Bali Hai is a lovely vacation rental inside a world renowned golfing resort in Montego Bay, Jamaica.
Trinity Villa is a recently renovated luxury vacation rental in Montego Bay with amazing Staff and wonderful ambiance in Jamaica.
Aquamarina Villa on the Sandy Beaches of Ocho Rios Jamaica, is a luxury vacation rental with full staff which is trained in high level services.
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.
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.
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.
As you turn right into the driveway from Copperwood Ridge and begin to ascend, you will wonder how much more of the ocean panorama will be seen once you alight at the top.
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
For a taste of paradise where the waves lap the shore and the trade winds caress the palm trees, Karma Bay has all the attributes that make for an unforgettable experience
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
Hyde Park a beautiful home with a wonderful flow of open space, two swimming pools, very large bedrooms, superb bathrooms and ocean as well as hillside views.
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
Happy Hour Villa Jamaica, one of the most stunning new properties you'll find in Jamaica with all of the bells and whistles of a 5 star resort with your own personal Staff.
Makana is a luxury beachfront vacation rental in Discovery Bay, Jamaica with a wonderful staff and amenities.
Sundance is a beautiful vacation rental in Montego Bay, Jamaica within a world class golfing resort Tryall Club.
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
Hummingbird House is a luxury rental in Montego Bay in the world renowned Tryall Club & Resort Golfing & Beach community. This special place is really just the icing on the cake of a family trip with everything you can want form beach clubs to amazing kids clubs and boating right on site.
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.
Zion Hill is a lovely vacation rental in Montego Bay, Jamaica which sits amidst six acres of immaculate garden with ocean views.
Harmony Hill in Montego Bay Jamaica is a luxury vacation rental with every amenity you can ask for in a Caribbean Vacation.
Phoenix is a luxury vacation rental on the ocean in Montego Bay, Jamaica with a full staff and resort amenities.
The Roundhouse Villa is a wonderful family friendly vacation rental inside the Tryall Gated Resort with beautiful ambiance and amenities.
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 nestled in the hills of Jamaica, overlooking pristine forests and the spectacular turquoise waters of Montego Bay.
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 in Montego Bay, Jamaica is a stunning vacation rental inside the world renowned Golfing Resort of Tryall with beach club.
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.
From Jamaica with Love: this grand-scale James Bond style escape is a breath-taking hideaway which can be yours to enjoy!
Malatai Villa is a gorgeous new modern beachfront vacation rental in Jamaica, within the Ocho Rios beachfront estates.
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.
Set in the historic fishing village of Discovery Bay on Jamaica's northern coast, Sundown villa gives a taste of a hidden Jamaica that not very many people know about.
Sea Salt is a new addition to dreamexoticrentals luxury portfolio, curating the most incredible villas that offer an epic spin on luxury vacation rentals.
Villa Sweet Villa is a vacation rental in Montego Bay, Jamaica with an outdoor swimming pool, a fitness center, a garden, a terrace and a bar.
Haystack Villa in Montego Bay is surrounded by rolling lawns with lovely sea and reef views to the front and a panorama of the Tryall estate to the east.
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.
