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Windward at Tryall in Montego Bay is just right for a family or group of friends.

Windward at Tryall Vacation Rental

There are a total of six bedrooms, each of them with its own bathroom. Lots of amenities will be found here that you won't find in other vacation spots. The beach is a short five-minute drive, which is especially great if you take the kids with you. The villa has both a kitchen and BBQ area, but you may want to eat out, too, and some of the best restaurants are only a few minutes' drive away. If you want to explore the area around you, you even have the option of using a golf cart! The staff is very helpful and will be happy to accommodate your needs. Windward Villa is a terrific destination for a family vacation.


All six bedrooms have HD cable television, state-of-the-art quiet remote control air conditioning, closet safes, ceiling fans and handsome Travertine marble en-suite bathrooms. Four bedrooms open to private furnished balconies and lovely sea views from both bedroom and bathroom. Two bedrooms downstairs open to furnished terraces, gardens and soft lawn.

An intentionally family-friendly floor plan consists of three master bedrooms, each adjacent to a children’s bedroom. For an all-adult group, all six bedrooms can be configured with kingsize beds.

Bedroom 1 - Master
Kingsize bed + daybed; en-suite bathroom with double-basin vanities, sunken bathtub and separate walk-in shower. French doors to furnished balcony.

Bedroom 2
Adjacent to Bedroom 1. Optional king or twin beds; en-suite bathroom with walk-in shower. French doors to furnished balcony and view.

Bedroom 3 - Master
Kingsize bed + daybed; en-suite bathroom with double-basin vanities, sunken bathtub and separate walk-in shower. French doors to furnished balcony and view.

Bedroom 4
Adjacent to Bedroom 3. Optional kingsize bed or twin beds; en-suite bathroom with walk-in shower. French doors to balcony and view.

Bedroom 5 - Master
Optional kingsize or twin beds + daybed; en-suite bathroom with bathtub and walk-in shower. French doors to furnished terrace, garden and soft lawn.

Bedroom 6
Adjacent to Bedroom 5. Optional kingsize or twin beds; en-suite bathroom with walk-in shower. French doors to furnished terrace, garden and soft lawn.

Tryall Club Membership

A significant amenity for guests in this villa is membership at the excellent Tryall Club. On 2,200 acres, Tryall’s golf course is among the most beautiful in the world. Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events. The resident pro offers workshops and private lessons. The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call. All white attire required. (Some Tryall Club golf services may be subject to a 15% service charge, including green fees, golf cart rentals, shoe and club rentals).

The beach is well planned for parents and children. Have lunch at the beach bar. Work out in the well-equipped gym. Jog the marked trails. Snorkeling, kayaking, hobie cat and sunfish are complimentary. Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees. Enjoy weekly events like the Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

On the hill, enjoy the historic Great House for afternoon tea and a magnificent view from the terrace. Shop at the commissary and boutique, meet for happy hour at the bar, and browse a wealth of Jamaican, Haitian and Cuban works and souvenirs in the Gallery of West Indian Art. And don’t miss the massive Tryall pool!

Membership Fee

Tryall is a private club whose 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.

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.

Plan to pay your Temporary Membership Dues locally at the Front Desk in the Great House when you register. Credit cards are accepted. You will be given a temporary membership card to enable your access to all Club facilities.

Tryall Club Front Desk will set up a charge account for you during your stay. If you plan to pay for your charge account in cash at the end of your stay, they will request a cash deposit. If you plan to pay for your charge account with a credit card, they will place a hold on your card to cover this amount (recommended hold amount is US$150 per adult per day).

Rates Table Key:

  Travel Dates      Bedrooms

 Minimum Stay      Starting Price

Travel Dates
Min. Night Stay
Min. Stay
Now to Apr 19, 2019 47
$ 2,597  2344 $ 3744 $ 3545  2660 £ 2006
/per night
Now to Apr 19, 2019 67
$ 2,922  2637 $ 4212 $ 3988  2993 £ 2257
/per night
Apr 20, 2019 to Apr 26, 2019
$ 2,922  2637 $ 4212 $ 3988  2993 £ 2257
/per night
Apr 27, 2019 to Nov 22, 2019 45
$ 1,558  1406 $ 2246 $ 2127  1596 £ 1203
/per night
Apr 27, 2019 to Nov 22, 2019 65
$ 1,623  1465 $ 2340 $ 2215  1663 £ 1254
/per night
Nov 23, 2019 to Nov 30, 2019
$ 1,948  1758 $ 2808 $ 2659  1996 £ 1505
/per night
Dec 1, 2019 to Dec 14, 2019 45
$ 1,558  1406 $ 2246 $ 2127  1596 £ 1203
/per night
Dec 1, 2019 to Dec 14, 2019 65
$ 1,623  1465 $ 2340 $ 2215  1663 £ 1254
/per night
Dec 15, 2019 to Dec 20, 2019 47
$ 2,597  2344 $ 3744 $ 3545  2660 £ 2006
/per night
Dec 15, 2019 to Dec 20, 2019 67
$ 2,922  2637 $ 4212 $ 3988  2993 £ 2257
/per night
Dec 21, 2019 to Dec 27, 2019
Christmas rates apply to any 7 night booking that includes Christmas Day
$ 3,896  3516 $ 5616 $ 5318  3991 £ 3009
/per night
Dec 28, 2019 to Jan 4, 2020
New Year’s rates apply to any 7 night booking that includes New Year’s Eve
$ 3,896  3516 $ 5616 $ 5318  3991 £ 3009
/per night

Taxes & Fees of 15% must be applied to the villa rental rate (Government Consumption Tax of 10% + Tryall Club Administration Fee of 5%)
5% service charge applies for holiday weeks. A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas and New Year’s Eve.

Security Deposit: $2,000

Minimum Stay: Minimum night stay may vary by villa. Please contact a villa specialist to confirm.

Important! Non-USD rates above based on approximate currency conversion. Please confirm rate and currency with your Villa Specialist at time of booking.

Bathroom Details
  • Bathrobes
  • Hair Dryers
  • 6 bedrooms, 6 en-suite bathrooms, 2 powder rooms
  • 4 daybeds for children (complimentary rails available)
  • Heated private pool
  • Staff of 6
  • Lovely views of the Caribbean Sea
  • 2 acres of spacious, landscaped grounds with soccer goals and lawn games
  • iPod docks in all rooms (can broadcast through sound system)
  • WiFi throughout
  • Office with printer/fax/copier/scanner and daybed for an additional child
  • Sirius XM radio with 200 channels
  • 5-speaker sound system in house and pool bar
  • Covered poolside bar lounge with fridge, TV, ping pong and powder room
  • Handicap accessible: 36” doorways, seamless entrances to large showers
  • Perfect family home, extremely child friendly
  • Option of all kingsize beds or 2 kings + 8 twins
  • 2 complimentary transportation carts (4- and 6-seaters)
Pool Details
  • 32' by 17' private solar heated swimming pool
Staff and Services
  • Butlers
  • Chef
  • Gardener
  • Housekeeper
  • Laundress
Location Details
  • Beach: 5 minutes by complimentary golf cart to Tryall Club private beach
  • Town: 25 minutes via driver
  • Airport: 25 minutes via driver
Villa Notes
  • Check-In: 3:00 PM
  • Check-Out: 12:00 PM
  • Tryall Club charges for early check-in (before 3pm) and late check-out (after 12 noon)
  • Maximum desired occupancy is 15 guests. Guests in excess of 12 will attract a nightly surcharge of US$30 each.
Jamaica Villa Notes
  • Most Jamaican rental villas come with a full staff, consisting of cook, maid, and laundress. A private cook will prepare breakfast, lunch, and dinner -- meals that you choose based on your own personal tastes.
  • A prepaid refundable security/damage deposit is required by most Jamaican Villas usually $500 - $1000 per stay. Please inquire with your Villa Specialist for exact amounts at time of booking.
Additional Villa Notes
  • A typical grocery budget is $55-$65 per adult per day and $25 per day for children. This may vary up or down depending on market prices and menus.

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Free Nights »

Book now and stay 7 nights for the price of 5.

Valid for new bookings made now to 4/19/19 for travel 6/1/19 to 8/31/19. Blackout dates may apply. 7 night minimum booking required. Subject to availability and may not be combinable with other offers. Additional restrictions may apply; please call for full details.

Jamaica Travel Guide

Out of Many, One People

One of the Caribbean’s most popular villa destinations, Jamaica has something for everyone and every occasion. Many venture to Jamaica to tan and relax on the breathtaking beaches, while others come to enjoy the plethora of activities. Avid snorkelers and scuba divers can discover the beautiful coral reefs and exotic marine life. Coffee lovers will take pleasure in the delicious home-grown coffee from the famous Jamaican Blue Mountains, which are also ideal for hiking and horseback riding. Sightseers will want to climb the world-famous 600-foot-high Dunn's River Falls, and bird-lovers will enjoy the Rocklands Feeding Station, home to Jamaica’s 27 native species. Those who want to see beautiful sunsets should partake in the Jamaican tradition and head over to the famous Rick’s Cafe in Negril, where visitors will not only see magnificent sunset views, but also watch brave cliff-jumpers dive into the crystal-clear water.

A villa vacation in Jamaica is unique in that many of our villas come with a full staff (chef, butler, housekeeper and laundress) included. The friendly staff will treat you with their “No problem, mon” service, where everything you desire is at your beck and call.

Learn more about Jamaica »

Villa information may change without notice and should be confirmed with our villa rental specialists.

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