Cliffside Cottage is perched dramatically on a lush green hillside next to the Caribbean Sea. The cottage is one of the most beautiful villas in Jamaica that provides a fantastic view of the deep blue sea during the day, and the romantic lights that sparkle across Montego Bay through the night. The mesmerizing sunsets and sunrises from the wrap-around verandah at Cliffside Cottage are spectacular. 


Cliffside Cottage has five delightfully decorated bedrooms, fully air-conditioned and comfortable. The décor in each room is unique because of high-quality fabrics and superb furnishings. The cottage is maintained meticulously and is one of the finest luxury villas in Jamaica.


The spacious living room looks even more impressive with its high rafter-and-beam ceiling. The living room opens into a wrap-around verandah which provides a picture-perfect view and the coolest trade winds. The CD and DVD collections, fabulous sound system and Digital Satellite System provide excellent options for entertainment within the Jamaica villa.


Cliffside Cottage has a large and inviting swimming pool, just a few steps from the house, accompanied by a lovely sunlit terrace. Beautifully adorned with exotic fuchsia and purple bougainvillea, the terrace attracts Jamaica’s exotic Doctor Bird. The pool terrace is the perfect spot for Tia Maria or after-dinner coffee, or even for a romantic dance in the beautiful Jamaican moonlight. 


Lavish home-cooked meals prepared by the professional staff can be served in the colorful and comfortable indoor dining room or on the breezy covered east verandah with the Montego Bay in view. At the guests’ request, lavish poolside dinner parties can also be organized. The well-trained and experienced staff ensures that the household functions smoothly, making the visitors’ stays at one of the best villa rentals in Jamaica, the most memorable ever.



**   The Tryall Club membership:  beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, new Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, beach parties Mon-Wed-Fri ** Tryall temporary membership fee applies for all guests


Master Bedroom
Queensize mahogany canopy bed, private balcony with ocean view, side porch and walkway to pool, en-suite bath with large walk-in shower. Privately located in new wing. Locked area for valuables.

Bedroom 2
Queensize mahogany bed, door to terrace with ocean view, en-suite bath with tub-shower combination. Opens to interior garden with landscape lights and walkway to living room. Also connects through passageway to Bedroom 3.

Bedroom 3
Kingsize or twin beds at guests’ option. French doors open to view over pool and sea. En-suite bathroom with double vanity and tub-shower combination. Also connects through passageway to Bedroom 2. Privately located in new wing.

Bedroom 4
Kingsize or twin beds at guests’ option. Garden view. Hall bath with walk-in shower.

Bedroom 5
Kingsize or twin beds at guests’ option. Garden view. Private hall bath with tub-shower combination.



A significant amenity for guests in this villa is membership at the excellent Tryall Club.  On 2,200 acres, Tryall’s golf course is among the most beautiful in the world.  Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events.  The resident pro offers workshops and private lessons.   The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call.  All whites required.

The beach is well planned for parents and children. Have lunch at the beach bar.  Work out in the well-equipped gym.  Jog the marked trails. Snorkeling, kayaking, hobie cat and sunfish are complimentary.  Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees.  Enjoy the week’s events, including the Monday Night Manager’s Cocktail Party and the Wednesday and Friday night beach parties (Friday Seafood Night on the Beach Buffet is excellent).

On the hill, enjoy the historic Great House for afternoon tea and a magnificent view from the terrace.  Shop at the commissary and boutique, meet for happy hour at the bar, and browse a wealth of Jamaican, Haitian and Cuban works and souvenirs in the Gallery of West Indian Art.  And don’t miss the massive Tryall pool!

Wait! Please contact us before you auto book! Our calendars are changing hourly and we want to triple check that the dates are still available and make sure that your chosen villa is suitable for you.  We want to share so many things about this villa and the booking process. We have inspected our villas personally so don’t be shy to contact us! We would like to tell you all the finer points, the highlights, the distance from the airport, the nearest grocery store, the staff, transportation on island, what your cook/chef can prepare for you, expectations for tipping the staff, make sure there are no hidden details or hidden costs….. things that may be important for your group! Speak to us! Email us all your questions! We want your vacation to run smoothly!







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Rooms Details

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