The Tryall Club requires all villa and condo guests to become a member during their stay via a temporary membership fee of $160 (plus 15% service charge) per week for guests 16 years and older, or $32 (plus 15% service charge) per person per day for stays of less than seven days. For children 12 years and younger, the membership fees are complimentary.
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 veranda that captures the breathtaking view and refreshing trade winds.
Wonderful home-cooked meals are served on the breezy covered east veranda with a view of Montego Bay across the water, or in the cozy and colourful 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.
| Category | Date Range | Rate | Min stay |
|---|---|---|---|
| Apr 16 - Nov 17, 2023 (3 Bedrooms) | Apr 16, 2023 to Nov 17, 2023 | $786 per Night$5,500 per Week | 5 Nights |
| Nov 26 - Dec 14, 2023 (3 Bedrooms) | Nov 26, 2023 to Dec 14, 2023 | $786 per Night$5,500 per Week | 5 Nights |
| Dec 15 - Dec 18, 2023 (3 Bedrooms) | Dec 15, 2023 to Dec 18, 2023 | $1,129 per Night$7,900 per Week | 7 Nights |
| Jan 3 - Mar 29, 2024 (3 Bedrooms) | Jan 3, 2024 to Mar 29, 2024 | $1,129 per Night$7,900 per Week | 7 Nights |
| Apr 8 - Apr 15, 2024 (3 Bedrooms) | Apr 8, 2024 to Apr 15, 2024 | $1,129 per Night$7,900 per Week | 7 Nights |
| Apr 16 - Nov 22, 2024 (3 Bedrooms) | Apr 16, 2024 to Nov 22, 2024 | $786 per Night$5,500 per Week | 5 Nights |
| Dec 1 - Dec 14, 2024 (3 Bedrooms) | Dec 1, 2024 to Dec 14, 2024 | $786 per Night$5,500 per Week | 5 Nights |
| Dec 15 - Dec 18, 2024 (3 Bedrooms) | Dec 15, 2024 to Dec 18, 2024 | $1,129 per Night$7,900 per Week | 7 Nights |
| Category | Date Range | Rate | Min stay |
|---|---|---|---|
| Apr 16 - Nov 17, 2023 (5 Bedrooms) | Apr 16, 2023 to Nov 17, 2023 | $1,000 per Night$7,000 per Week | 5 Nights |
| Nov 18 - Nov 25, 2023 (5 Bedrooms) | Nov 18, 2023 to Nov 25, 2023 | $1,143 per Night$8,000 per Week | 7 Nights |
| Nov 26 - Dec 14, 2023 (5 Bedrooms) | Nov 26, 2023 to Dec 14, 2023 | $1,000 per Night$7,000 per Week | 5 Nights |
| Dec 15 - Dec 18, 2023 (5 Bedrooms) | Dec 15, 2023 to Dec 18, 2023 | $1,272 per Night$8,900 per Week | 7 Nights |
| Dec 19 - Dec 26, 2023 (5 Bedrooms) | Dec 19, 2023 to Dec 26, 2023 | $1,858 per Night$13,000 per Week | 7 Nights |
| Dec 27 - Jan 2, 2024 (5 Bedrooms) | Dec 27, 2023 to Jan 2, 2024 | 7 Nights | |
| Jan 3 - Mar 29, 2024 (5 Bedrooms) | Jan 3, 2024 to Mar 29, 2024 | $1,272 per Night$8,900 per Week | 7 Nights |
| Mar 30 - Apr 7, 2024 (5 Bedrooms) | Mar 30, 2024 to Apr 7, 2024 | $1,272 per Night$8,900 per Week | 7 Nights |
| Apr 8 - Apr 15, 2024 (5 Bedrooms) | Apr 8, 2024 to Apr 15, 2024 | $1,272 per Night$8,900 per Week | 7 Nights |
| Apr 16 - Nov 22, 2024 (5 Bedrooms) | Apr 16, 2024 to Nov 22, 2024 | $1,000 per Night$7,000 per Week | 5 Nights |
| Nov 23 - Nov 30, 2024 (5 Bedrooms) | Nov 23, 2024 to Nov 30, 2024 | $1,143 per Night$8,000 per Week | 7 Nights |
| Dec 1 - Dec 14, 2024 (5 Bedrooms) | Dec 1, 2024 to Dec 14, 2024 | $1,000 per Night$7,000 per Week | 5 Nights |
| Dec 15 - Dec 18, 2024 (5 Bedrooms) | Dec 15, 2024 to Dec 18, 2024 | $1,272 per Night$8,900 per Week | 7 Nights |
| Dec 19 - Dec 26, 2024 (5 Bedrooms) | Dec 19, 2024 to Dec 26, 2024 | $1,858 per Night$13,000 per Week | 7 Nights |
| Dec 27 - Jan 2, 2025 (5 Bedrooms) | Dec 27, 2024 to Jan 2, 2025 | $2,000 per Night$14,000 per Week | 7 Nights |
| Damage WaiverNon-refundable | $99 Flat | |
| Service Fee | $50 Flat |
| Check-in time: | 15:00 | Check-out time: | 11:00 |
• Rooms are for priced for double occupancy only. Extra guests may be approved by the homeowner and an extra guest fee may be applied.
• The rates for this property are dynamic and are constantly changing. The price listed above is only a starting rate and does not necessarily reflect the price for your travel dates. Please contact a reservations agent for exact pricing details.
• Staff gratuity - 10% (high season) to 15% (low season) of villa rental rate is to be paid to the head of house in Jamaican or US Dollars at the end of the stay.
Cliffside Cottage is equipped with an array of included amenities and services:
• Personal service by the villa staff including a chef, butler, housekeeper, laundress, gardener and security guard
Amenities and services available upon request (extra cost):
• Cost of food and beverages
• Villa pre-stocking/grocery delivery
Industry Association Recommended Cleaning Practice: SafeHome
| Bedroom 1 | Primary | 1 King | 2 Guests | Additional Info |
| Bedroom 2 | 1 Queen | 2 Guests | Additional Info |
| Bedroom 3 | 1 King | 2 Guests | Additional Info |
| Bedroom 4 | 1 King | 2 Guests | Additional Info |
| Bedroom 5 | 1 King | 2 Guests | Additional Info |
| Bathroom 1 | Primary | Toilet, Shower | En-suite |
| Bathroom 2 | Toilet, Shower | En-suite |
| Bathroom 3 | Toilet, Tub/Shower Combo | En-suite |
| Bathroom 4 | Toilet, Shower | |
| Bathroom 5 | Toilet, Tub/Shower Combo | En-suite |
Montego Bay, Jamaica
13 minutes to Tryall Club.
20 minutes to the airport.
Tisha J.
Jun 13, 2022
Hidden Treasure!
I travel frequently, the Cliffside Cottage has been the best vacation I have had in years. The rooms are decorated with lots of colors, the beds are very comfortable, and the scenery from our private balcony was breathtaking. The staff made us feel very welcome, they were friendly and catered to our every need. It was like visiting family. Patricia, the housekeeper was like having a caring loving mother with you. The food the chef prepared each day was out of this world, Derrick, the butler was amazing. And the groundskeeper and security made us feel safe. I celebrated my birthday at the villa and the staff made me feel so special. We had such an amazing experience that we have already booked the villa for next year.
Rashad B.
Aug 6, 2019
Peaceful Jamaica
Villa and house service was terrific. Me and my family will definitely be visiting again. The lovely family there that took care of us are a gift from God. They met all our needs and were marvelous. Love them to my heart. The contract language and details was poorly communicated. Cost prices, meals, groceries, etc. needs to be more clear up front.
Richmond R.
Jun 7, 2019
Jamaica mon!
I found your website as I googled luxury Caribbean rentals. I called and Sarah Murphy was SO helpful in researching available properties/locations for me! My family thoroughly enjoyed our stay at the Cliffside Cottage in Jamaica and can’t wait to do it again! I
Alex L.
Dec 3, 2018
Adventure escape!
Since the first contact until the end of our holidays, everything was perfect. We very much enjoyed the villa that we rented which had a great staff. The service provided by Amanda and Tim was on the spot. Thank you very much!
One of our villa experts will contact you to help you plan your unique villa experience.
Contact us at 1-800-208-5097
9:00 a.m. - 8:30 p.m. EST Mon - Fri
Create an account
Follow Us
