The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee of US$160 (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate of 50% (plus a 15% service charge). Guests can also pay per day, US$32 (plus a 15% service charge),for guests ages 16 and older who stay for one to four days. This can be either prepaid or upon arrival at the Club.
For children 12 years of age and younger, our Temporary Memberships 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 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 |
| Jan 3 - Apr 18, 2025 (3 Bedrooms) | Jan 3, 2025 to Apr 18, 2025 | $1,129 per Night$7,900 per Week | 7 Nights |
| Apr 27 - Nov 21, 2025 (3 Bedrooms) | Apr 27, 2025 to Nov 21, 2025 | $786 per Night$5,500 per Week | 5 Nights |
| Nov 30 - Dec 14, 2025 (3 Bedrooms) | Nov 30, 2025 to Dec 14, 2025 | $786 per Night$5,500 per Week | 5 Nights |
| Dec 15 - Dec 18, 2025 (3 Bedrooms) | Dec 15, 2025 to Dec 18, 2025 | $1,129 per Night$7,900 per Week | 7 Nights |
| Category | Date Range | Rate | Min stay |
|---|---|---|---|
| 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 |
| Jan 3 - Apr 18, 2025 (5 Bedrooms) | Jan 3, 2025 to Apr 18, 2025 | $1,272 per Night$8,900 per Week | 7 Nights |
| Apr 19 - Apr 26, 2025 (5 Bedrooms) | Apr 19, 2025 to Apr 26, 2025 | $1,272 per Night$8,900 per Week | 7 Nights |
| Apr 27 - Nov 21, 2025 (5 Bedrooms) | Apr 27, 2025 to Nov 21, 2025 | $1,000 per Night$7,000 per Week | 5 Nights |
| Nov 22 - Nov 29, 2025 (5 Bedrooms) | Nov 22, 2025 to Nov 29, 2025 | $1,143 per Night$8,000 per Week | 7 Nights |
| Nov 30 - Dec 14, 2025 (5 Bedrooms) | Nov 30, 2025 to Dec 14, 2025 | $1,000 per Night$7,000 per Week | 5 Nights |
| Dec 15 - Dec 18, 2025 (5 Bedrooms) | Dec 15, 2025 to Dec 18, 2025 | $1,272 per Night$8,900 per Week | 7 Nights |
| Dec 19 - Dec 26, 2025 (5 Bedrooms) | Dec 19, 2025 to Dec 25, 2025 | $1,858 per Night$13,000 per Week | 7 Nights |
| Dec 26 - Jan 2, 2026 (5 Bedrooms) | Dec 26, 2025 to Jan 2, 2026 | $2,000 per Night$14,000 per Week | 7 Nights |
| Damage WaiverNon-refundable damage waiver (up to $2,000) | $299 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.
Cindy H.
Jul 6, 2023
Fabulous 50 Birthday celebration
Besides the property being immaculate, Ms. Patricia and her staff were so very welcoming and friendly. They made our experience memorable.
Brittany D.
Mar 27, 2023
Vacation Extraordinaire!
Rental Escapes did an amazing job of finding us a gorgeous property to rent while in Jamaica. We started to book a little too late and were struggling to find a villa to rent on the beach but Tania Lee really saved the day finding us a fully-staffed Villa up in the hills with sweeping views of the sea. Our vacation was more than I could ever have hoped for. I will definitely be using their services again in the future.
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!
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