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Cliffside Cottage

What we like most
  • Dramatic hillside location with stunning views of the Caribbean Sea
  • Large living room opening to a wrap-around verandah
  • Pool terrace for moonlit dancing and after-dinner relaxation
Insider's Knowledge
  • Sunrise and sunset vistas are mesmerizing
  • After-dinner coffee or Tia Maria on the pool terrace
  • Cliffside Cottage guests have membership at The Tryall Club for beach and tennis privileges
Places close by
  • The Tryall Club for additional activities (6 minutes drive from villa)
  • Rocklands Bird Sanctuary (17 minutes drive from villa)
  • Doctors Cave Beach (20 minutes drive from villa)


Welcome to Cliffside Cottage, a luxury 5 bedroom private villa, dramatically perched on a lush green hillside above the sea in Montego Bay.

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 high rafter-and-beam ceiling. This space opens wide to a wrap-around verandah that captures the breathtaking view and refreshing tradewinds.

Just steps from the house are the large pool and sunny terrace trimmed in exotic purple and fuchsia bougainvillaea 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 six-minute drive brings guests to The 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.

STAFFDuring your stay at Cliffside Cottage you will have a wonderful team of staff to look after you, including your own cook, housekeeper, laundress and gardener/night watchman. Wonderful home-cooked meals are served on the breezy covered east verandah with Montego Bay's view across the water ... or in the cosy and colourful indoor dining room. The staff will also create romantic poolside dinner parties under the stars at guests’ request.

• 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
• air conditioning in all bedrooms
• staff of 5: cook, 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
• Tryall Club Temporary Membership Fee (see paragraph below) *

*The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee of US$130 (plus 15% service charge) per week for each guest 16 years and over, or US$26 (plus 15% service charge) per day per person for stays of less than 7 days. 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 tennis shop, ball boys, bar & restaurant, spa, grocery, motorized watersports, nanny services and golf.

Complimentary amenities include the beach, non-motorized watersports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party and various special events.

Check out all that the Tyrall Resort Jamaica has to offer you and your family. Enjoy the ultimate Jamaican vacation at the Tyrall Resort.


Master Bedroom
In private east wing. Kingsize 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. Locked area for valuables.

Bedroom 2
Queensize 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 the 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. Private hall bath with tub-shower combination.

Villa Features
• 5 Bedrooms, 5 Bathrooms
• Sleeps 10 People
• 5,000 Interior Square Ft.
• 4 Staff
• Air Conditioning
• Children Welcome
• Fully Staffed Villa
• Golf Available Tryall Club (member). Across town: Cinnamon Hill, Half Moon, White Witch
• Internet Wireless
• Pool
• iPod Dock(s)
• Hair Dryers
• Round Hill member
• Connecting Bedroom(s)
• Kids Club Membership
• Complimentary Calls to the US, UK and Canada
• Wireless Internet Access
• Full Gym Nearby (walk, drive or take golf cart)
• Golf on Site or Nearby
• Tennis Nearby
• Available for Large Groups
• Available for Weddings
• Cook or Chef Vetted as Gourmet
• Spa on Site or Nearby


Montego Bay
Nearest airport Montego Bay Airport
21.8 km


  • Bedroom(s): 5 ( Sleeps 10 )
    4 King, 1 Queen
  • Bathroom(s): 5
    2 Baths, 5 Showers, 5 Wash basins, 5 Toilets
  • General facilities: Balcony / Deck, Ceiling Fans, Garden, Garden View, Gated Entrance, High Speed Internet, Panoramic Views, Parking, Private Location, Private Terrace, Security, Terrace, Wifi
  • Indoor facilities: Air conditioning, All Bedrooms Air Conditioned, DVD Player, iPOD Docking Station, Media Room, Phone, TV
  • Services: Breakfast included, Chef Included, Cleaning inclusive, Concierge Service, Linen provided, Maid service, Towels provided
  • Access: Off-road parking, Secure parking, Private car park


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  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 1,000 - $ 2,000 $ 7,000 - $ 14,000 5 Nights -
Low Season 2024 16-Apr-2024 - 22-Nov-2024 $ 1,000 $ 7,000 5 Nights -
Thanksgiving 2024 23-Nov-2024 - 30-Nov-2024 $ 1,143 $ 8,000 7 Nights -
Low Season 2024 01-Dec-2024 - 14-Dec-2024 $ 1,000 $ 7,000 5 Nights -
High Season 2024 15-Dec-2024 - 18-Dec-2024 $ 1,272 $ 8,900 7 Nights -
Christmas 2024 19-Dec-2024 - 26-Dec-2024 $ 1,858 $ 13,000 7 Nights -
New Year 2024 27-Dec-2024 - 02-Jan-2025 $ 2,000 $ 14,000 7 Nights -
High Season 2025 03-Jan-2025 - 18-Apr-2025 $ 1,272 $ 8,900 7 Nights -
Easter 2025 19-Apr-2025 - 26-Apr-2025 $ 1,272 $ 8,900 7 Nights -
Low Season 2025 27-Apr-2025 - 21-Nov-2025 $ 1,000 $ 7,000 5 Nights -
Thanksgiving 2025 22-Nov-2025 - 29-Nov-2025 $ 1,143 $ 8,000 7 Nights -
Low Season 2025 30-Nov-2025 - 14-Dec-2025 $ 1,000 $ 7,000 5 Nights -
High Season 2025 15-Dec-2025 - 18-Dec-2025 $ 1,272 $ 8,900 7 Nights -
Christmas 2025 19-Dec-2025 - 25-Dec-2025 $ 1,858 $ 13,000 7 Nights -
New Year 2025 26-Dec-2025 - 02-Jan-2026 $ 2,000 $ 14,000 7 Nights -

Additional Information


  • Damage Waiver Fee: $149.00


Our stay at the villa was amazing.
Our stay at the villa was amazing.

Hi Noreen & Emma- Thanks again so much for arranging everything, we had a great time! Our stay at the villa was amazing. The staff were all so attentive, I don't think there's a single thing anyone would have changed! The driver was lovely and it was so fun checking out another area in Jamaica.Definitely hope to go back again sometime in the future! Thanks again so much!

By Retief Party
The house and staff are fabulous.
The house and staff are fabulous.

Happy New Year Emma & Noreen, Thanks we had a great time. The house and staff are fabulous. Round Hill Club was very nice indeed. The Golf course of Tryall is absolutely fantastic. All in all it was great, thank you for your attention.

By Repenning Party
Cliffside Cottage is a 5 star villa
Cliffside Cottage is a 5 star villa

Dear Emma, 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.

By Kimberly W. Party

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Expert Reviews

Great Villa

Expert Review Pic This is a really beautiful villa in Montego Bay. I love the dining/bar area, it is a fun place to relax and unwind. The villa has a great pool area, friendly staff and spacious bedrooms. What else do you need to enjoy a great vacation....maybe a Rum Punch!

By From Exceptional Villas

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Alannah Harrington

Our team know each destination and every villa we feature.

We also offer a personalized and fully complimentary concierge service so every part of your trip will be taken care of ensuring you have a hassle free vacation.

We look forward to hearing from you.

    • Type: Villa
    • Sleeps: 10
    • Bedroom(s): 5
    • Bathroom(s): 5
    • Board: Catered
    • Long term rentals: No
    • Pets: No
    • Children: Yes, great for kids
    • Wheelchair: No
    • Eldery or infirm: Yes
    • Holiday type: Family, Fully Staffed, Sea Views, Wedding Villas