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
  • staff of 5: butler, 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
  • complimentary calls to the US and Canada
  • wireless Internet
  • magnificent panorama of Montego Bay, Caribbean Sea, sunrises, sunsets
  • Round Hill membership: complimentary beach, two connecting heated pools for parents & children, jogging trail, Manager's Cocktail Party. For various fees: Pineapple Kids Club, fitness room, tennis, hair salon & spa, bars & restaurants, gift shops, water sports, Internet room, 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 six-minute drive brings guests to Round Hill resort 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. 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 minutes from the villa and one of the finest private resorts on Jamaica's North Coast.  Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, afternoon tea and Wednesday Manager's Cocktail Party ... and unforgettable long sunsets from the waterfront terrace.  For additional charges, members may enjoy the spa, tennis courts, Pineapple Kids Club, fitness center, salon, a range of water sports and beach parties (Monday-Wednesday-Friday). Internet access is $22 per day for up to 3 devices. This may be paid at reception. The internet service can be upgraded to Premium (faster speed) for $33 per day for up to 3 devices.

Round Hill was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world."

Rental Rates

Season Bedrooms Weekly Rate
High Season
December 15 - April 15
1–3 $7,200
High Season
December 15 - April 15
4–5 $8,400
Low Season
April 16 - December 14
1–3 $5,000
Low Season
April 16 - December 14
4–5 $6,500
March 26 - April 2
1–5 $8,400
November 21 - November 28
1–5 $7,000
December 19 - December 26
1–5 $11,500
New Year
December 26 - January 2
1–5 $12,500
Link to Calendar

Booking Calendar

Guest Reviews

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