Jamaica Villas by Linda Smith

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Cliffside Cottage • Montego Bay, Jamaica Villa

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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
  • new bar is located on the veranda with outdoor dining area
  • air conditioning in all bedrooms
  • private safes in each bedroom
  • staff of 5: chef, butler, 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
  • complimentary calls to the US and Canada
  • wireless Internet
  • magnificent panorama of Montego Bay, Caribbean Sea, sunrises, sunsets
  • Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night. Current membership runs through November 30, 2018. See note below*

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 few minutes' drive brings guests to Tryall Club where Cliffside guests have membership for beach and tennis privileges and, for various fees, a range of other activities including the Kids Club to keep youngsters entertained.


Master Bedroom
In private east wing. Kingsize 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.

Bedroom 2
Queensize mahogany bed, French doors to terrace with ocean view, en-suite bathroom with large walk-in shower. 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. En-suite bathroom with tub-shower combination.

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 white attire required.

The beach is well planned for parents and children. Have lunch at the beach bar.  Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it).  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 weekly events like  complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

On the hill, enjoy the historic Great House for daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar.  Also at the Great House is the new Usain Bolt Games Room open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs and HDTV. And don’t miss the massive Tryall pool. The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads and everyone from teens to octogenarians.

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.”

*NOTE: Tryall Club membership is guaranteed for guests travelling through November 30, 2018. Some villa beach memberships are not guaranteed if travel dates are beyond November 30, 2018. Ask our Villa Specialists if you have any questions.

Rental Rates

Season Bedrooms Weekly Rate
Low Season 2018
April 16 - December 14
1–3 $4,500
Low Season 2018
April 16 - December 14
4–5 $6,000
Thanksgiving 2018
November 17 - November 24
1–5 $7,000
Christmas 2018
December 19 - December 26
1–5 $11,500
New Year's 2018-2019
December 26 - January 2
1–5 $12,500
High Season 2019
December 15 - April 27
1–3 $6,900
High Season 2019
December 15 - April 27
4–5 $7,900
Easter 2019
April 20 - April 27
Easter week is any 7 nights that includes Easter Sunday
1–5 $7,900
Link to Calendar

Booking Calendar

Guest Reviews

  • Staff and service was great. Great food, lots of variety.

    We loved our stay would love to return.

    Crispin C - April 2018

  • Superb staff, Outstanding service! Incredible accommodations! Lovely time by all!

    Danielle C - March 2018

  • Everything with respect to the staff & service was outstanding! Exceeded expectations. Thank you! Meals were delicious, perfect.

    Accommodations overall excellent, we felt very much at home. Thanks for a wonderful stay!

    Terri B – March 2018

  • The staff is very warm, friendly. Everything is perfect. Excellent meals.

    Ken T – March 2018

  • A wonderful week for our family of 10. Perfect for ages 4-67!

    The staff was completely warm and welcoming from the moment we arrived. We felt completely taken care of. Delicious meals! We left every menu up to Chef Benford and each one was wonderful.

    We could not have had a better week. The house and grounds are well cared for and beautiful, very comfortable.

    Robert B – February 2018

  • Exceptional staff!! Enjoyed being with them. Accommodations were excellent. Cliffside exceeded our expectation and will plan to return!

    Sheila O – July 2017

  • We had such an awesome time while in Jamaica!! The staff that was there 18 yrs ago when I first visited were just as kind and loving as the first time that I met them!! I am excited to start planning my vacation for next year!!!

    Thanks again for all your help!

    Kim W – May 2017

  • My family and friends had a great time at your property in Jamaica. The staff were perfect,,,I would not hesitate to recommend this property to friends and family. Thanks for providing great hospitality!

    Walker - June 2016

  • Superb! Exceeded our expectations. All the staff were friendly and accommodating – they made our trip very special.

    Jason N - March 2016

  • Wonderful service & beautiful villa! We had such a great time that we will be definitely returning!

    Alliya M - March 2016

  • All of the staff were amazing. Michael, Clifford & Pat were outstanding. We loved the villa and will recommend to our friends!

    Mark S - December 2015

  • Staff, Service & accommodations were excellent!

    Sarah H - July 2015

  • We loved all the staff who went above and beyond to see that we were comfortable, happy and safe. Having access to the two clubs was a real bonus for our group of young adults. We could all be together and enjoy a variety of activities. Our first experience with having a staff was a real luxury. Truly makes the vacation a holiday, especially for our Mom.

    Connie D - December 2014

  • Staff are all excellent! Taking them all home!!

    Clifford C - June 2014

  • Absolutely wonderful! Superb! The staff is amazing and attended to our every need. Cliffside will be recommended.

    Perry C. - July 2014

  • Dear Linda,

    The entire staff was amazing! We were welcomed and treated with love for our entire visit. The house is updated and beautiful all around - pool and grounds. So tidy and clean,laundry was wonderful too! Clifford was kind, reliable and always on time with a smile. I would return and recommend absolutely!

    Annu G - Okemos MI - May 2014

  • Dear Linda,

    The staff made our trip special.

    Shirley R. - Gatlinburg, TN - January 2014

  • Dear Linda,

    The staff is amazing. Hope to be back soon.

    Raymond D. - Toronto, Canada - December 2013

  • Dear Linda,

    Had a wonderful stay. The staff is awesome. Loved all of them. We will hopefully return soon.

    Barry F. - Alpharetta, GA - July 2013

  • Dear Linda,

    I will not hesitate to recommend this villa to anyone who wants to visit Jamaica! We have enjoyed every minute. We love the staff. Ms. Patricia is by far more than anyone could ever ask. She displays grace and elegance when serving guests. Cliffside Cottage is a 5 star villa. You can't ask for anything better. Great location & great view.

    Kimberly W. - Houston, TX - July 2013

  • Dear Linda,

    Such a nice, warm welcome that continued throughout the entire stay. The house is beautiful and filled with an excellent staff. Can't wait to return and bring a group.

    Anne and Nathan J. – New York, NY – November 2012

  • Dear Linda,

    This was a wonderful stay! The staff was around when we needed them, and everything was thought of ahead of time! Awesome chef! Beautiful views! We recommend Cliffside Cottage. It exceeded our expectations and we hope to return!

    John & Lisa E., Homer Glen, IL, April 2012

  • 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

  • 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

  • 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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Jamaica Villas by Linda Smith 100 Fordham Road, Bldg. C Wilmington, MA, 01887 Tel 301.229.4300 Email info@jamaicavillas.com
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