Cliffside Cottage

Caribbean / Jamaica / Montego Bay

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.

up to 5
up to 10
from 5
Min. Nights


  • five-bedroom five-bath private villa with a 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
  • the new bar is located on the veranda with an outdoor dining area
  • air conditioning in all bedrooms
  • private safes in each bedroom
  • the staff of 5: chef, butler, housekeeper, laundress, gardener/night watchman
  • cable television with a 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, the Caribbean Sea, sunrises, sunsets
  • Cliffside Cottage has a membership to the Tryall Club

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 a 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 an 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 the private east wing. King-size mahogany canopy bed, French doors to a private balcony with ocean view, French doors to side balcony and walkway to pool, en-suite bathroom with large walk-in shower.

Bedroom 2
Queen-size mahogany bed, French doors to terrace with ocean view, en-suite bathroom with large walk-in shower. French doors to the interior garden with landscape lights and a walkway to the living room. Adjoining passageway with Bedroom 3.

Bedroom 3
King-size or twin beds at the guest's 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
King-size or twin beds at the guests' option along with a day bed. Garden view. Hall bath with walk-in shower.

Bedroom 5
King-size or twin beds at the guest’s option. Garden view. En-suite bathroom with tub-shower combination.

Tryall Club Membership:

  A Temporary Membership Fee of US$26 per person per day plus a 15% service charge for any guest 16 years and older will be required.   Payment will be made at the Front Desk in the Great House upon arrival.    

After paying the Temporary Membership Fee, members may use most Club facilities at no charge with the exception of the tennis shop, ball boys, bar & restaurant, spa, grocery, motorized water sports, nanny services, and golf.  Complimentary amenities include the beach, non-motorized water sports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party, and various special events.

*Please Note: Tryall Club membership is guaranteed for guests traveling through November 30, 2023. Some villa beach memberships are not guaranteed if travel dates are beyond November 30, 2023. Ask our Villa Specialists if you have any questions. There may be occasions when some or all the facilities of the hotel may be closed for membership guest services due to a private hotel event. The Tryall Club reserves the right to change or alter its membership packages with no advance notice.


5 Bedrooms, 5 Bathrooms

Sleeps 10 Guests

5000 Interior Square Ft.

  • Child Friendly: Connecting Bedroom(s)
  • Child Friendly: Kids Club Membership
  • Golf and Tennis: Golf on Site or Nearby
  • Audio: iPod Dock(s)
  • Communications: Complimentary Calls to the US, UK and Canada
  • Communications: Wireless Internet Access
  • Distant ocean view
  • Golf and Tennis: Tennis Nearby
  • Chef
  • Butler
  • Housekeeper
  • Gardener
  • Night Watchman
  • Fitness Equipment: Full Gym Nearby (walk, drive or take golf cart)
  • Beach Club & Resort Membership: Tryall Club (outside the gate)
  • Membership to the Tryall Club. A Temporary Membership Fee of US$26 per person per day plus a 15% service charge for any guest 16 years and older will be required. Payment will be made at
  • Other: Spa on Site or Nearby
  • Weddings (up to 50 people)
  • Bathrooms: Hair Dryers
  • Private safes in each bedroom


Bedroom Details

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.

Distance Details

Beach: 13 minutes to the Tryall Club
Town: 20 minutes via driver
Airport: 20 minutes

Rates and Availability

Security Deposit Details
US $99 Damage Deposit Waiver Fee: A US $99 Damage Deposit Waiver Fee applies to your reservation. It is our goal to ensure that you have a remarkable experience at our villas. And we understand that accidents happen. In lieu of a large security deposit, your reservation will include a $99 Accidental Damage Waiver fee. This will cover accidental damages of up to $2,000 that occur during your stay.

Check-In Times
Check in: 3:00 PM - Check out: 11:00 AM
Rate Policies

A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas and New Year’s Eve.

Wedding Details
Maximum guests: 50
Surcharge for festive bookings
5% surcharge for festive bookings

Exclusive Offers

Take your vacation to the next level, with 2 free airline tickets.* For a limited time, every reservation over $50,000 will receive an airline reimbursement worth up to $1,000 - any airline, any destination. Imagine flying in style to your handpicked villa located in one of the most beautiful destinations around the world, knowing that you've saved on the cost of your flights. This is your chance to experience the ultimate in luxury travel and indulge in the vacation of a lifetime.

*Free air promotion is valid new bookings only and cannot be applied to existing bookings. Valuation based on two round trip tickets using the bureau of Transportations U.S. average flight price for 2022. Receive up to a $1,000 reimbursement for flights upon presentation of a flight receipt. Minimum booking value of $50,000 applies. The booking value applies to the villa cost only and does not include any additional services or fees. This offer is valid for bookings made 2/20/2023 through 4/02/2023 for travel now through 12/31/2024. Bookings made outside of this period will not be eligible. The $1,000 air credit offer is non-transferable, has no cash value, and cannot be redeemed for any other service. The airline credit will be applied to your booking once your villa rental has been paid in full. The airline credit will be redeemed by providing a receipt of your booked flight and a check will be sent to you within 15 business days of providing flight documentation. All offers are subject to availability. We reserve the right to modify or cancel this promotion at any time without notice.



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

We loved our stay would love to return.

Crispin C.

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.

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

Ken T.

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.

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

Sheila O.

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.

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!


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

Jason N.

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

Alliya M.

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

Mark S.

Staff, Service & accommodations were excellent!

Sarah H.

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.

Staff are all excellent! Taking them all home!!

Clifford C.

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

Perry C.

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.

Dear Linda,

The staff made our trip special.

Shirley R.

Dear Linda,

The staff is amazing. Hope to be back soon.

Raymond D.

Dear Linda,

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

Barry F.

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.

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.

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.

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.

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.

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.

Very comfortable. Five star service!

Slade party

Everyone went above and beyond. Patricia is very hospitable and addressed all needs asap. Benford made great good and executed beatifically. Derrick was professional and made great drinks. Clifford A+ driver. Allison did a herculean job and Renville made us feel safe and kept the grounds immaculate.

Wertheimer Party

I was so relaxed at the villa. The service was amazing.

Hagood party

The staff exceeded our expectations in every way. The attention to detail surpasses any 5 star hotel. They were inviting and treated us like family. Truly unforgettable. We are grateful for their efforts. Accommodations felt like a home away from home. Clifford was phenomenal as a driver. We also appreciated his recommendations. The only thing that's upsetting is having to leave.

Chef Benford - His culinary skills had us eager to come back home. His meals made our trip more memorable. We all were amazed how he was able to accommodate every request. Ms. Patricia - I instantly felt comfortable around her. Ms. Patricia's energy was always inviting and positive. I valued her maternal guidance and oversight. Mr. Derrick - we are truly grateful for everything Derrick did for us. He was always available with a warm smile. He was courteous and a phenomenal bartender. Mr. Renville - We felt secure knowing Mr. Renville watched over us. No matter the time of night our family could sleep well with him around. Mr. Moullett- Her efforts behind the scenes wasn't unnoticed. We appreciated having fresh laundry every day. We didn't have to worry about anything staying here. Thank you.

Collings Party

We enjoyed everyone. Everyone was great. Thank you for everything! We loved Cliffside!

Excellent service. I would return to the villa and recommend to others.

Burton Family

Staff was excellent. We will definitely be back.

Russell Party

We loved it, it was fabulous. The only reason we would not return is if there were no access to Tryall. Our kids really enjoyed being able to go to Tryall and enjoy beach activities there.

Doolittle Party

The staff was amazing, like family almost. Personable, kind, & made our stay just like home. Beautiful property - clean comfy, & the grounds were beautiful as well. Excellent driver, Clifford was awesome, knowledgeable, & very attentive & kind.

Davis Party

All Meals were spectacular. Everything was always kept clean. Staff always friendly and available to help! The staff took extra care of our 4 year old to be sure he was happy! The grounds are impeccable! Just lovely! Would love to return and will recommend.

Wing Family

The staff was perfect. They were very attentive. Every meal we requested was made. All the food was delicious. Everything was very clean. Clifford the driver was great. He made sure we stayed safe and gave us good ideas to visit. I have been to Jamaica 2 times, but this is the first time I stayed at a villa. Patricia, Benford, & Renville made this the best vacation ever because of the staff. I will only be vacationing at Cliffside Cottage.


This was the best experience ever!

Capers Party

The staff and service and accommodations were outstanding! Our expectations were exceeded and we would return & recommend the villa to others.

Bersano/ Janish party

We couldn't have been any happier with the staff!! Great people! We felt very welcome and comfortable - would love to have stayed another week. Perfect views too! Would absolutely return to this villa and recommend to others.

Treadwell/ Santimauro/Loggins Party

Patricia - Great house mom
Benford - Respectful chef and gentleman
Derrick - The face to our Jamaican vacation
Renville - Our kindly watchman
Tristan - Helpful & a ready smile
Moulette - Always there for all of us.

Nevitt Party

House and staff were amazing! Five stars!

Moulton & Montazeni Party

Overall amazing staff!! We left very spoiled. Met above our expectations!!

-Skauge Party

Staff & Service: A+/Wonderful
Accommodations: A+/Excellent Vacation
I love it here!

-Sewrattan Party

Staff & Service: Excellent
Accommodations: Excellent
We will be back each year.

-Gayle Party

Staff & Service: Excellent
Accommodations: Excellent
Will return and recommend to others

-Bolton Party

Everyone was fantastic!
It was beautiful.
Staff was great.
We loved it here!

-Kelsey Party

The chef was very excellent!
Everyone was very nice towards us.
I would recommend this place to anyone.

-Paye Party

Excellent staff and service and we felt like we were in heaven! Exceeded expectations. As our kid said, it's the best cook of the world! Cliffside Cottage is a real jewel. Driver Clifford delivered an excellent service. Excellent overall experience and wonderful holiday.

Scharer Family

Amazing! Fabulous! Wonderful! Loved it. Renville does an excellent job. Clifford was on top of every detail. House was very comfortable. View spectacular! Staff was great.


We found everyone so kind and wonderful and attentive to all our needs...super friendly!!

DeMuth/ Sapir

Excellent service. Friendly staff who anticipated all our needs.

Gibson and Spencer Families

Lovely group of people who were warm and helpful.
The dinners were delicious! Table presentation & service...excellent!
The view is divine. The fresh flowers were lovely
Staff & Service: Excellent
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded

-Kelsey Party

Villa information may change without notice and should be confirmed with our villa rental specialists.

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