Cliffside Cottage , stunning view
Listing Description
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
- private safes in each bedroom
- staff of 5: 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
- wireless Internet
- magnificent panorama of Montego Bay, Caribbean Sea, sunrises, sunsets
- Cliffside Cottage has membership to the Tryall Club
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 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.
Accommodations
Master Bedroom
In private east wing. King-size 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 large walk-in shower. 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. En-suite bathroom with tub-shower combination.
5 Bedrooms, 5 Bathrooms – Sleeps 10 Guests
5000 Interior Square Ft.
Beach: 13 minutes to the Tryall Club
Town: 20 minutes via driver
Airport: 20 minutes
Tryall Club Membership:
All guests must pay a resort entry fee of US$32 per person per day plus a 15% tax to have access to the resort amenities at the Tryall Club. Children 13-15 years of age pay a discounted rate of 50% off plus 15% tax and children 12 & under are complimentary.
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.
Tryall Membership : All guests must pay a resort entry fee of US$34 per person per day plus a 15% tax to access the resort amenities at the Tryall Club. Children 13-15 years of age pay a discounted rate of 50% off, plus 15% tax, and children 12 & under are complimentary.
After paying the Temporary Membership Fee, members may use most Club facilities at no charge except for 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, 2025. There may be occasions when some or all of the hotel facilities 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 without advance notice.
Rates are on daily basis including services of the full villa staff
| Travel Dates | Bedrooms | Minimum Night Stay | Nightly Rates |
|---|---|---|---|
| High Season: 7-night minimum stay required Low Season: 5-night minimum stay required Holidays: A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas, and New Year’s Eve. *Rates are subject to change without notice. Please check with your villa specialist to confirm. |
|||
| January 03, 2026 – April 03, 2026 High Season |
3 | 7 | $ 1128 * |
| January 03, 2026 – April 03, 2026 High Season |
5 | 7 | $ 1271 * |
| April 04, 2026 – April 11, 2026 Easter – Any 7 nights that includes Easter Sunday |
5 | 7 | $ 1271 * |
| April 12, 2026 – April 15, 2026 High Season |
3 | 7 | $ 1128 * |
| April 12, 2026 – April 15, 2026 High Season |
5 | 7 | $ 1271 * |
| April 16, 2026 – November 20, 2026 Low Season |
3 | 5 | $ 785 * |
| April 16, 2026 – November 20, 2026 Low Season |
5 | 5 | $ 1000 * |
| November 21, 2026 – November 28, 2026 Thanksgiving Holiday |
5 | 7 | $ 1142 * |
| November 29, 2026 – December 14, 2026 Low Season |
3 | 5 | $ 785 * |
| November 29, 2026 – December 14, 2026 Low Season |
5 | 5 | $ 1000 * |
| December 15, 2026 – December 18, 2026 High Season |
3 | 7 | $ 1128 * |
| December 15, 2026 – December 18, 2026 High Season |
5 | 7 | $ 1271 * |
| December 19, 2026 – December 26, 2026 Christmas Holiday – Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally, any 7 nights (eg, Dec 17-24) that prevent a Christmas reservation will be invoiced at the Christmas rate. |
5 | 7 | $ 1857 * |
| December 27, 2026 – January 02, 2027 New Year’s Holiday: New Year – Dec 26-Jan 2 or Dec 27-Jan 3, or any 7 nights that include Dec 31st. |
5 | 7 | $ 2000 * |
Availability
| M | T | W | T | F | S | S |
|---|---|---|---|---|---|---|
| 1 | ||||||
| 2 | 3 | 4 | 5 | 6 | 7 | 8 |
| 9 | 10 | 11 | 12 | 13 | 14 | 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | 29 |
| 30 | 31 | |||||
| M | T | W | T | F | S | S |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | 26 |
| 27 | 28 | 29 | 30 | |||





