Windward at the Tryall Club - Montego Bay
6 Bedrooms
7 ½ Bathrooms
Swimming Pool
6 Staff
Children Welcomed
US$1558 per night View All Rates
 Call us

Direct: 1 246 622 4466
Freephone UK: 0 800 08 85574
Toll Free US: 1-866-404-9600
Toll Free Canada: 1-866-404-9600

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Luxury • Fabulous Pools • Stunning Sunsets • Cool Kitchens • Gorgeous Gardens • Fitness First • Family-Getaways • Relaxed Luxury • Golf • Tennis • Groups & Events
Favourite Features
  • Cool beanbag floaters -perfect for chilling out in the pool.
  • Impressive art collection in various mediums throughout the villa.
  • Spacious, tropically landscaped grounds with soccer goals and lawn games.
  • Situated within the fantastic Tryall Golf and Country Club.
  • Friendly and welcoming staff will make your stay easy and relaxed! No worries!
Good to Know
  • The Tryall Beach Club is just 5 minutes by complimentary golf cart.
  • Ideal for families- beds can be configured to suit most combinations of family or friends!
  • Wheelchair accessible- large doors and easy entry showers.
  • Maximum desired occupancy is 15 guests. Guests in excess of 12 will attract a nightly surcharge of US$30 each.
  • Temporary membership of The Tryall Club is US$100 per week per adult.


6 bedrooms - Up to 12 Guests
US$ 1,623 - US$ 3,896
Nightly Rate
12/15/2017 - 04/15/2018
US$ 2,922
US$ 243.50
03/31/2018 - 04/07/2018
US$ 2,922
US$ 243.50
04/16/2018 - 12/17/2018
US$ 1,623
US$ 135.25
11/17/2018 - 11/24/2018
US$ 1,948
US$ 162.33
12/18/2018 - 12/27/2018
US$ 3,896
US$ 324.67
New Year
12/27/2018 - 01/05/2019
US$ 3,896
US$ 324.67
4 bedrooms - Up to 8 Guests
US$ 1,558 - US$ 2,597
Nightly Rate
12/15/2017 - 04/15/2018
US$ 2,597
US$ 324.63
04/16/2018 - 12/17/2018
US$ 1,558
US$ 194.75
P.P.P.N. - Price Per Person per Night • 1 Bedroom (Bdrm) Sleeps 2 people.
This is not a booking rate but simply an indication of value based on maximum occupancy.
Nightly Rates listed are for accommodations only and do not include Food & Beverage, unless expressly stated.

Rental Rates are nightly and subject to 10% Government Consumption Tax and 1.5% Service Fee


Windward is a newly built villa enjoying an enviable location within the lovely environs of the world-renowned Tryall Club. With six bedrooms and an additional 4 daybeds for children, Windward is an excellent choice for families and groups of friends looking for comfort, luxury and style.

The excellent staff -comprising a chef, butler, housekeeper and laundress- are dedicated to ensuring guests of Windward are able to relax and fully enjoy the superb amenities and service of the villa.

The entrance is on the upper floor and opens onto a large open plan living area with wonderful views to the Caribbean Sea below and Montego Bay to the east.

Four bedrooms are on the upper level and enjoy private furnished balconies, HD cable television in each room and those signature views from both the bedroom and en-suite bathrooms!

Tastefully furnished to complement the contemporary design, the accommodation is beautifully accented by an eclectic selection of Caribbean art in various mediums.

Two additional bedrooms are downstairs and have access to the lawned garden via their furnished terraces. Also on the lower level is the impressive pool (heated from December to April) and spacious sun deck which has comfortable sun loungers and shades. Windward is set in over two acres of tropically landscaped grounds and features a selection of lawn games and soccer goals -ideal for children and adults alike!

A covered poolside bar lounge has a fridge for keeping those all important drinks at the perfect temperature. It also features a table tennis table, cable TV and a powder room. A state of the art sound system throughout the house and pool bar is enhanced by iPod docks in all the rooms allowing all musical tastes to be satisfied; Wi-Fi is of course available throughout.

The office features a printer/fax/copier and accommodates a daybed which can accommodate a child.

Windward at The Tryall Club is both extremely family and child friendly (complimentary rails are available for the four daybeds) and also handicap accessible. The doorways are 36" wide and the entrance to the large showers is seamless. The bedrooms can be configured as all king size beds or two king size beds and eight twin beds for maximum flexibility.

Maximum desired occupancy of Windward is 15 guests. Guests in excess of 12 will attract a nightly surcharge of US$30 each.

General Amenities

  • Barbeque
  • Billiard/Pool table
  • CD player
  • Ceiling Fans
  • DVD player
  • Fax Machine
  • Foosball
  • Gym - (shared)
  • Hair Dryers
  • Home Theatre
  • Inland (5 - 10 minutes from beach)
  • iPod Dock
  • Pool Shower
  • Spa nearby
  • Stereo
  • Table Tennis
  • TV with Cable
  • Wet Bar
  • Wi-Fi

Bedroom Amenities

  • Air-conditioned bedrooms

Security Amenities

  • Guard (Shift 12 hr)
  • Security Safe

Sporting Amenities

  • Tennis Court nearby
  • Golf Course nearby
  • Watersports nearby

Complimentary calls to the US, UK and Canada.

Bathrobes provided.

Kayaks and snorkel gear provided.

2 Complimentary transportation carts (4- and 6-seaters).

5-Speaker sound system in house and pool bar.

Sirius XM radio with 200 channels.

Housekeeper/ Laundress
Room NameConfigurationDescription
Master BedroomKing+ Daybed.
Master BathroomTub, En suite, Shower, Double Vanity
Bedroom 2KingOptional king size or twin beds.
Bathroom 2En suite, Shower only
Bedroom 3King+ Daybed.
Bathroom 3Tub, En suite, Shower, Double Vanity
Bedroom 4KingOptional king size or twin beds.
Bathroom 4En suite, Shower only
Bedroom 5KingOptional king size or twin beds and daybed.
Bathroom 5Tub, En suite, Shower
Bedroom 6KingOptional king size or twin beds.
Bathroom 6En suite, Shower only

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