Jamaica Villas by Linda Smith

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Windward at the Tryall Club • Montego Bay, Jamaica Villa

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About Windward at the Tryall Club

Premier Villa on Two Acres on Tryall Club’s Chic West End!

  • 6 bedrooms, 6 en-suite bathrooms, 2 powder rooms
  • 4 daybeds for children (complimentary rails available)
  • heated private pool
  • staff of six: chef, butlers, housekeeper, laundress, gardener
  • 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)
  • 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)*


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.

Additional Information

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

Click Here for Windward at the Tryall Club 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 4 Agile Turf courts and 5 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 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 2018
January 6 - April 14
1–4 $18,182
High Season 2018
January 6 - April 14
5–6 $20,455
Low Season 2017
April 15 - December 20
1–4 $10,909
Low Season 2017
April 15 - December 20
5–6 $11,364
March 31 - April 7
Easter week is any 7 nights that includes Easter Sunday
1–6 $20,455
November 18 - November 25
1–6 $13,636
December 19 - December 26
1–6 $27,273
New Year's
December 26 - January 2
1–6 $27,273
Link to Calendar

Booking Calendar

Guest Reviews

  • The staff was professional, kind & fun! They made our stay at Tryall great fun! Thank you for making our stay exceptional.

    Kirk S - January 2015

  • The staff are personable, professional & made our trip. The attention to details was amazing. They went above & beyond. We will return every year.

    Jessie W - January 2015

  • Dear Linda,

    Windward is amazing. The house is beautiful and the staff is great. Damion is charming and professional and made us feel at home immediately. And Chef Knight is very talented - the food has been fantastic. Just wanted to let you know how much we appreciate everything!

    Kim B. - New York, NY - February 2013

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Villas by Linda Smith 100 Fordham Road, Bldg. C Wilmington, MA, 01887 Tel 301.229.4300 Email linda@jamaicavillas.com
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