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Cliffside Cottage 2 to 5 Bedroom , Montego Bay - Jamaica

About Cliffside Cottage, Montego Bay Jamaica

Cliffside Cottage is a beautiful 5-bedroom, 5-bath private hillside villa located about 15 minutes west of Montego Bay. This charming villa features panoramic ocean & city views. A short walk from the villa veranda is the large private pool with a beautiful cut stone pool terrace / beautiful views of Montego Bay can be enjoyed from this terrance. The 5,000 square feet of living space includes plenty of veranda space for outdoor dining and relaxing, as well as indoor living and dining room rooms that have wonderful ocean views!

Cliffside Cottage includes:
*Wireless Internet Access
*Bedrooms # 1, 2, 3, & 5 all have en-suite baths
*Bedroom #4 has a hall bath with walk in shower
*20' x 40' private pool and large cut stone pool terrace
*new bar is located on the veranda near the outdoor dining area
*air conditioning in all bedrooms
*private safes in each bedroom
*your staff with include a 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

The new 5th bedroom wing has a private walkway to the pool and pool deck area ~ The wonderful landscaping of colorful croton, beautiful bougainvillea, hibiscus and Jamaican Almond Trees only add to the charm of this unique private villa.

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
Queen size 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
King size 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
King size or twin beds at guests' option along with day bed. Garden view. Hall bath with walk-in shower.

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

* Cliffside Cottage includes membership to the Tryall Club *
Please note all guests will incur the Temporary Membership Fee of US $32. + 17.5% service charge) per visit per person.
Children between the ages of 13 and 15 years pay a discounted rate of US $16 plus a 17.5% service charge.
For children 12 years and younger, the Temporary Membership Dues are complimentary.

Plan to pay this TMD fee at the Front Desk in the Great House when you check in for your visit.

Amenities include the Tryall private beach, non-motorized water sports such as kayaks, paddle boards, snorkeling equipment, hobi cat, and Sunfish if available, tennis, the air-conditioned fitness room, Usain Bolt games room & Internet Room, both located in the Great House, jogging trails, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party and various special events.

*Membership will also include Afternoon Tea - served daily and a weekly manager's cocktail party for all guests. You can also enjoy the large Great House Pool.

* NOTE *
The Tryall Club membership is guaranteed for guests travelling through November 30, 2023.
This beach membership is not guaranteed if travel dates are beyond November 30, 2023.

"Tryall Club Temporary Membership"

Click Here for details: "Tryall Club Temporary Membership Dues"

Click Here for:  Things To Do ~ Sites to See
Click Here for:  Restaurants in Montego Bay
Click Here for:  Golf Courses in Jamaica


Dear Vicki
Our stay was WONDERFUL. The property and views were even more lovely than the photos. The staff was excellent, I felt sad saying goodbye to them!
Overall we loved everything about Cliffside. Thank you, Kristie

Dear Vicki,
Cliffside Cottage was great and so was the staff! The meals were excellent! The staff members were very accommodating and we enjoyed seeing Lloyd who was our butler six years ago at Blue Heaven! Thank you!!

Dear Vicki.
We had the best time at Cliffside last week. Our family was in heaven and the staff was amazing. Thank you thank you thank you for all of your coordination and guidance. We could not have asked for a better experience. The food was awesome. Benford was so kind and sweet. He made special plates for the kids and knew our likes/dislikes. Clifford was great. We called him the Mayor because he knew everyone everywhere. We went to Mayfield Falls and to Chukka Ziplines as well as MVP jerk shack and SkyBar. I am ready to go back!! Thank you, Anne
(another family member in Anne's group)
Vicki, It was more and more than we ever imagined. LOVED every minute of it.
Cannot thank you enough for your amazing hard work and all of our questions answered.
We are grateful to you and always happy to help in any way we can if you ever need us.
Also, the staff is amazing in EVERY WAY! They are like our family! Thank you! Beth

Dear Vicki,
We loved every minute of your trip and stay at Cliffside, and are already planning our return for 202! We loved the meals and the accommodation made for diets, likes and dislikes. Christmas dinner was especially heartfelt and memorable! The staff members were amazing and the villa was perfect and we can't wait to return. We love Jamaica! Thank you, Braggs, Warrens and Hacketts ~

Dear Vicki,
Our stay at Cliffside exceeded my expectation and most of that can be attributed to the staff, we can't thank them enough! They were the friendliest and most caring people - Ten out of ten for all of them! The villa was perfect for our group of 10 adults, very clean and comfortable overall. We would return. Thank you, Ian

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!


  • Queen Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Safe
  • Shower Only
  • Linens/Towels

COMMON AREA Living/Dining

  • Telephone
  • Internet Access
  • Cable/Satellite TV
  • DVD Player
  • CD Player
  • Radio
  • Patio / Balcony
  • Ceiling Fan
  • Indoor Dining
  • Outdoor Dining


  • Queen Bed
  • Ceiling Fan
  • Air Conditioning
  • Safe
  • Bathtub w/Shower
  • Linens/Towels


  • King Bed
  • Ceiling Fan
  • Air Conditioning
  • Safe
  • Bathtub w/Shower
  • Dual Sinks
  • Linens/Towels


  • Two Twin Beds
  • Air Conditioning
  • Safe
  • Shower Only
  • Linens/Towels


  • King Bed
  • Ceiling Fan
  • Air Conditioning
  • Safe
  • Bathtub w/Shower
  • Linens/Towels

Half Bath/Powder Room

  • Linens/Towels


  • Bathtub w/Shower

Full Kitchen

  • Refrigerator
  • Cooking Range
  • Oven
  • Microwave Oven
  • Freezer
  • Coffee Maker
  • Blender
  • Juicer
  • Toaster

Property Amenities

  • Freshwater Pool (Private)
  • Full Staff
  • Parking
  • Yard
  • Deck/Patio
  • Outdoor Dining
  • Child Friendly


  • Beach (driving distance)
  • Activity Coordinator
  • Bicycling
  • Boat Rentals
  • Craft Market
  • Deep Sea Fishing
  • Duty-Free Shopping
  • Golf
  • Gym
  • Spa Facilities
  • Hiking
  • Horseback Riding
  • COMMON AREA Living/Dining
  • Kayaks
  • Pool Table
  • Sailing
  • Diving
  • Snorkeling
  • Sunfish Sailboats
  • Tennis
  • Tour Desk
  • Volleyball
  • Water Skiing
  • Wind Surfing
  • Jet Skis

Montego Bay, Jamaica

Rates in USD - Holidays may attract higher rates


April 16 - November 22, 2024  Low Season
3 bedroom  $ 786 

5 bedroom $ 1,000 

November 23 -  30, 2024
Thanksgiving  5 bedroom $ 1,143 

December 01 - 14, 2024 Low Season
3 bedroom  $ 786 
5  bedroom $ 1000

December 15 - 18, 2024 High Season
3 bedroom $ 1129 
5  bedroom $ 1272 


December 19 -  26, 2024
Christmas Holiday - Dec 19-26 or 20-27 or any 7 nights

that includes Dec 25th. Additionally any 7 nights (eg. Dec 17-24)

 invoiced at the Christmas rate. 5 bedroom $ 1858 
December 27, 2024 - January 02, 2025

New Year's Holiday- Dec 26-Jan 2 or Dec 27-Jan 3

or any 7 nights that includes Dec 31st.   $ 2000 


January 03, 2025 - April 18, 2025
High Season    3 bedroom  $ 1129 

January 03, 2025 - April 18, 2025
High Season    5 bedroom  $ 1272 

April 19, 2025 - April 26, 2025
Easter - Any 7 nights that includes Easter Sunday  $ 1272 

April 27, 2025 - November 21, 2025 Low Season
3 bedroom  $ 786 
5  bedroom $ 1000 

November 22 - 29, 2025
Thanksgiving Holiday  $ 1143 

November 30 - December 14, 2025 Low Season
3 bedroom  $ 786 
5 bedroom $ 1000 

December 15 - 18, 2025 High Season
3  bedroom $ 1129 
5 bedroom  $ 1272 

December 19, 2025 - December 26, 2025
Christmas Holiday- Dec 19-26 or 20-27 or any 7 nights

that includes Dec 25th. Additionally any 7 nights (eg. Dec 17-24)

 at the Christmas rate.   $ 1858 

December 26, 2025 - January 02, 2026
New Year's Holiday  - Dec 26-Jan 2 or Dec 27-Jan 3

or any 7 nights that includes Dec 31st.  $ 2000 


Rates are subject to change without notice

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