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Tradewinds at the Tryall Club • Montego Bay, Jamaica Villa

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About Tradewinds at the Tryall Club

This cozy home sits on two acres at the famous Tryall Club ~ directly on the Caribbean Sea. 300 feet of waterfront form the north perimeter of the property.

  • 4-bedroom waterfront private villa at the famous Tryall Club 
  • full staff: chef, housekeeper, laundress, gardener
  • cable television ... DVD ... radio-cassette-CD player
  • 18' x 34' swimming pool
  • complimentary golf cart
  • complimentary DSL Internet access
  • The Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, new Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night.
  • Tryall Club Temporary Membership Fee (due at check-in, see paragraph below)*

This cozy home sits on two acres at the famous Tryall Club ~ directly on the Caribbean Sea.  300 feet of waterfront form the north perimeter of the property.  The water here is excellent for swimming and snorkeling.  Sometimes the sea is as smooth as glass.  Sometimes its waves break dramatically against the sea wall.  Windsurfing here is superb.

To the east of the house is a large grassy lawn, wonderful for children's games.  The beach club, pro shop, driving range, first tee, and casual beach bar and restaurant are a three-minute walk or a one-minute golf cart ride.

In the living room is the entertainment center with cable television, sound system and library of videos and CD's.  A wet bar adjoins the living room.  Ten glass-paneled doors open to the spacious verandah and pool terrace, generously furnished with chaise lounges, tables and chairs.  Stone steps lead from the terrace directly into the water.  Most meals are served here on the breezy terrace near the sea.  In addition to the outside dining table,  Tradewinds also has an inside dining room with seating for ten under a whimsical chandelier.  One wall of the dining room opens wide to a lush garden of tall tropical plants, beautifully lighted each night.

At each day's end, the sound of waves lapping nearby lulls guests to sleep.


All four bedrooms are air conditioned.

Master Bedroom
Kingsize four-poster bed; en-suite bathroom with walk-in shower.  Television.  Sitting room with daybed, mahogany desk, lovely ocean view.  Opens to terrace.

Bedroom 2
Kingsize or twin beds at guests’ option; en-suite bath with walk-in shower.  Connects through small interior passageway to Bedroom 3. 

Bedroom 3
Kingsize or twin beds at guests' option; en-suite bathroom with tub-shower combination.  Connects through small interior passageway to Bedroom 2.  Bedrooms 2 and 3 are appropriate for families as parents and children can share this two-bedroom connecting suite of rooms. 

Bedroom 4
Kingsize or twin beds at guests' option; en-suite bathroom with walk-shower. This bedroom is in a separate octagonal cottage on the edge of the pool terrace and just 20 feet from the main house.  Six French doors and 10 louvred windows open to a wonderful ocean view.

Additional Information

Click Here to see Floor Plan.

The 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.

The beach is well planned for parents and children. Have lunch at the beach bar.  Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it).  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  complimentary 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 daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar.  Also at the Great House is the new Usain Bolt Games Room open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs and HDTV. And don’t miss the massive Tryall pool. The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads and everyone from teens to octogenarians.

For a great write-up of the Tryall Club, see Dana Vachon's article Club Jamaica in Departures Magazine.

The Tryall Club was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world.”

Tryall Club Golf Course Note:  The front 9 holes of the golf course will be closed from May 13 - October 16, 2017 for extensive renovation. The recently renovated back 9 holes of the golf course will remain open all summer. Members & guests who wish to play 18 holes between May 13th and Oct 16th can play the back 9 holes twice. Multiple tee box options will be available in order to give a different feel to the golf course. The driving range will remain open as normal. All green fees during this period will be charged at our 9 hole rates regardless of whether the golfer plays 9 or 18 holes. Normal cart and caddy fees will apply.

*Tryall Club Temporary Membership Dues

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 per week for each guest 16 years and over, or US$26 per day per person for stays of less than 7 days.

Plan to pay your TMD fee at the Front Desk in the Great House when you register. They will also 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.

Rental Rates

  • Government Consumption Tax of 10% must be applied to the villa rental rate.
Season Bedrooms Weekly Rate
High Season
December 19 - April 17
1–4 $8,500
Low Season
April 18 - December 18
1–4 $4,500
April 10 - April 17
Easter week is any 7 nights that includes Easter Sunday
1–4 $8,500
November 18 - November 25
1–4 $4,500
December 19 - December 26
1–4 $11,050
New Year's
December 26 - January 2
1–4 $11,050
Link to Calendar

Booking Calendar

Guest Reviews

  • Dear Linda,

    We had a great time and had to mention what a fantastic job the staff at Tradewinds did. Every meal prepared by Vincent was a winner and Gina was superb on every level -- patient, organized, welcoming and funny.

    Bill F. – Albany, NY – November 2012

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