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Cliffside Cottage • Montego Bay, Jamaica Villa
About Cliffside Cottage
Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.
- five-bedroom five-bath private villa with remarkable view
- 5,000 square feet of indoor and outdoor living space on four acres
- 20' x 40' private pool and large cut stone pool terrace
- air conditioning in all bedrooms
- staff of 4: cook, housekeeper, laundress, gardener/night watchman
- cable television with large plasma screen, DVD and video library
- sound system, CD library and iPod dock with wireless speakers
- wireless Internet
- magnificent panorama of Montego Bay, Caribbean Sea, sunrises, sunsets
- Round Hill membership:
Complimentary: beach, tennis, two connecting heated pools for parents & children, jogging trail, Manager's Cocktail Party
For various fees: Pineapple Kids Club, fitness room, tennis lessons, hair salon & spa, bars & restaurants, gift shops, water sports, Internet room, beach parties Mon-Wed-Fri - The Tryall Club membership: complimentary beach, tennis, gym, heated
pool, Hummingbird Kids Club, non-motorized water sports, Internet room, art gallery, jogging trail, afternoon tea & Manager’s Cocktail Party. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, cigar & jewelry shop, motorized water sports, beach parties Mon-Wed-Fri
Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.
The central part of the villa is the large living room with high rafter-and-beam ceiling. This space opens wide to a wrap-around verandah that captures the breathtaking view and refreshing tradewinds.
Wonderful home-cooked meals are served on the breezy covered east verandah with a view of Montego Bay across the water ... or in the cozy and colorful indoor dining room. The staff will also create romantic poolside dinner parties under the stars at guests’ request.
Just steps from the house are the large pool and sunny terrace trimmed in exotic purple and fuchsia bougainvillea attracting Jamaica’s delicate Doctor Bird. A special treat is after-dinner coffee or Tia Maria served on the pool terrace. The pool terrace is also a wonderful spot for dancing in the moonlight under the great Jamaican sky.
A four-minute drive brings guests to Round Hill resort where Cliffside guests have membership for beach and fitness center privileges and, for various fees, a range of other activities including the Kids Club to keep youngsters entertained.
Accommodations
Master Bedroom
In private east wing. Queensize mahogany canopy bed, French doors to private balcony with ocean view, French doors to side balcony and walkway to pool, en-suite bathroom with large walk-in shower. Locked area for valuables.
Bedroom 2
Queensize mahogany bed, French doors to terrace with ocean view, en-suite bathroom with tub-shower combination. French doors to interior garden with landscape lights and walkway to living room. Adjoining passageway with Bedroom 3.
Bedroom 3
Kingsize or twin beds at guests' option. French doors to terrace with ocean and pool view. Large bay window with sunset views. En-suite bathroom with double vanity and tub-shower combination. Adjoining passageway with Bedroom 2.
Bedroom 4
Kingsize or twin beds at guests' option along with day bed. 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.
Round Hill Hotel and Beach Club Membership

A special amenity available to guests in this villa is membership at Round Hill ... just one minute from the villa and one of the finest private resorts on Jamaica's North Coast. Membership entitles guests to access Round Hill's private beach and tennis on hard-surface courts lit for night play and with pro on call. (Charges apply to lessons and ball boys.) Round Hill also offers a jogging trail, gift shop, logo shop, beach bar, piano bar, Continental cuisine in the hotel restaurant ... and unforgettable long sunsets from the waterfront terrace. For additional charges, members may enjoy the spa, Pineapple Kids Club, fitness center, a range of water sports and parties (Monday beach party, Wednesday Manager's Cocktail Party, Friday Jamaica Night). Round Hill has an annual closure - for 2012 Round Hill will be closed between September 4 - October 9.
Round Hill was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world."
The Tryall Club Membership
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!
For a great write-up of the Tryall Club, see Dana Vachon's article Club Jamaica in Departures Magazine.
The Tryall Club was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world.”
Tryall Club Temporary Membership Fee
Tryall is a private club whose members may use most Club facilities at no charge with the exception of golf, food and beverage, and spa services. Complimentary amenities include the beach, most water sports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party and various special events.
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee of US$100 per week for each guest 18 or older, or US$20 per day per person for stays of less than 7 days.
Plan to pay your Temporary Membership Fee locally at the Front Desk in the Great House when you register. Credit cards are accepted. You will be given a temporary membership card to enable your access to all Club facilities.
Rental Rates
| Season | Bedrooms | Weekly Rate |
|---|---|---|
| High Season December 15 - April 15 |
1–3 | $6,000 |
| High Season December 15 - April 15 |
4–5 | $7,000 |
| Low Season April 16 - December 14 |
1–3 | $3,500 |
| Low Season April 16 - December 14 |
4–5 | $5,250 |
| Christmas December 20 - December 29 |
1–5 | $11,500 |
| New Year December 29 - January 5 |
1–5 | $12,500 |
| Easter April 7 - April 14 |
1–5 | $7,000 |
| Thanksgiving November 19 - November 26 |
1–5 | $6,500 |
Booking Calendar
Guest Reviews
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Dear Linda,
The staff is excellent and they make things so easy! The villa is perfectly situated and appointed. This is the best "Linda Smith" villa yet!
John E - Homer Glen, IL - March 2011
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Dear Linda,
This staff is very friendly, helpful and polite and create an extremely pleasant atmosphere. We want to take the staff home with us because we love them do much - where did you find such nice people? The villa is exceptionally clean, the view is spectacular and we had a very relaxing vacation
Neema F. - Winter Park, FL - June 2010
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Dear Linda,
The entire staff made us feel at home! We had a great time and thank you and the local staff for everything!
Nedra H. - Fresno, TX - June 2010
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Dear Linda,
This staff was so attentive and made certain our needs were met at all times. The accommodations exceeded all our expectations.
We really enjoyed our stay at Cliffside
Cottage. Naturally, we can t wait until our next vacation in Jamaica to come back to the villa and this wonderful staff.
Beverly
O., May 2009
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Dear Linda,
I want to take a moment to tell you we had a wonderful time at Cliffside
Cottage. The accommodations were perfect and the staff was just outstanding. We are trying to arrange all our schedules to make a repeat trip next year so you will be hearing from us again.
Ellen
L., Aiken SC, Feb 2009
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Dear Linda,
The villa is lovely and we appreciate the constant maintenance that is apparent overall. The staff is wonderful and we have been very happy.
James S., Ontario Canada, Jan 2009
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Dear Linda,
The
Cliffside Cottage staff is, as always, excellent! We love them anf tjey make this villa the BEST! Montego Bay is beautiful but it is the villa experience that keeps us coming back! We want the homeowner to know how much we appreciate how willing she is to share her home, staff and this experience. A mere thank you is not enough!
Janet O., Moblie AL, Aug 2008
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Dear Linda,
What delicious meals! All members of the staff were very pleasant, courteous, professional and helpful. We loved the house.
Becky T., New York New York, Mar 2008
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Dear Linda,
At Cliffside Cottage the view is breathtaking. The villa is comfortable and relaxing and the staff is very good.
It is like a home away from home!
Arlington M., Jan 2008
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Dear Linda,
Cliffside Cottage has an efficient and very polite staff that has given us excellent service with integrity and warmth.
They made us feel very welcome. The decor of the villa is beautiful yet it is comfortable and child friendly.
We hope to return!
Tom S., Jan 2008











