Windward at the Tryall Club

Caribbean / Jamaica / Montego Bay

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

up to 6
Bedrooms
up to 12
Guests
8
Bathrooms
5
Min. Nights

Overview

  • 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)
  • Wi-Fi 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 king size beds or 2 kings + 8 twins
  • 2 complimentary transportation carts (4- and 6-seaters)
  • Tryall Club membership: complimentary beach, pickle ball, 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)*

Accommodations

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 king-size beds. 

MAIN LEVEL BEDROOMS
Bedroom 1 - Master
King-size 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
King-size 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 king-size bed or twin beds; en-suite bathroom with walk-in shower. French doors to balcony and view.

LOWER LEVEL BEDROOMS
Bedroom 5 - Master
Optional king-size 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 king-size 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.

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 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).


Features

6 Bedrooms, 8 Bathrooms

Sleeps 12 Guests

9500 Interior Square Ft.

Ping Pong

Fooseball Table

Tennis Nearby

Full Gym Nearby

Kids Club Membership

Tryall Club Membership

Located on Club Grounds

iPod Dock(s)

Communications: Complimentary Calls to the US, UK and Canada

Fully Staffed Villa

Golf and Tennis: Golf on Site or Nearby

Other: Available for Large Groups

Other: Handicap Accessible

Other: Spa on Site or Nearby

Pool Table

Playground Nearby

Wireless Internet Access

Heated Pool

Snorkel Gear

Kayaks

Hair Dryers

Bathrobes


Details

Pool Details

17' x 32'

Rates

Travel Dates Bedrooms Min. Night Stay Nightly Rates
April 24, 2022 - November 18, 2022
4 5 $ 1624 *
April 24, 2022 - November 18, 2022
6 5 $ 1715 *
November 19, 2022 - November 26, 2022
Thanksgiving- Rates on Request
6 7 Rates available upon request *
November 27, 2022 - December 14, 2022
4 5 $ 1624 *
November 27, 2022 - December 14, 2022
6 5 $ 1715 *
December 15, 2022 - December 18, 2022
4 7 $ 1949 *
December 15, 2022 - December 18, 2022
6 7 $ 2894 *
December 19, 2022 - December 26, 2022
Christmas rates apply to any 7 night booking that includes Christmas Day
6 7 $ 4068 *
December 27, 2022 - January 02, 2023
New Year’s rates apply to any 7 night booking that includes New Year’s Eve
6 7 $ 4068 *
January 03, 2023 - April 14, 2023
High Season
4 7 $ 2066 *
January 03, 2023 - April 14, 2023
High Season
6 7 $ 3098 *
April 15, 2023 - November 17, 2023
Low Season
4 5 $ 1715 *
April 15, 2023 - November 17, 2023
Low Season
6 5 $ 1858 *
November 18, 2023 - November 25, 2023
Thanksgiving - Rates on Request
4 7 Rates available upon request *
November 18, 2023 - November 25, 2023
Thanksgiving - Rates on Request
6 7 Rates available upon request *
November 26, 2023 - December 15, 2023
Low Season
4 5 $ 1715 *
November 26, 2023 - December 15, 2023
Low Season
6 5 $ 1858 *
December 16, 2023 - December 23, 2023
High Season
4 7 $ 2066 *
December 16, 2023 - December 23, 2023
High Season
6 7 $ 3098 *
December 24, 2023 - January 05, 2024
Christmas/New Year's Eve- 7 Nights may be accepted on request
4 14 $ 4131 *
December 24, 2023 - January 05, 2024
Christmas/New Year's Eve- 7 Nights may be accepted on request
6 14 $ 4215 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Rate Policies

A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas and New Year’s Eve.

Check In Times

Check in: 3:00 PM - Check out: 11:00 AM

Tax Service Charge Details *

A 10% Government Consumption Tax and Non-Refundable 5% Tryall Club Administration Fee applies to the villa rental.

Security Deposit Details

A refundable security deposit may be pre-collected. Please confirm with your villa specialist

Exclusive Offers

Reserve your dream villa and receive 5% back on your getaway.


5% Back offer is in the form of a digital BJ's Wholesale Club® e-Gift Card (GC) and is awarded to one guest per new 3+ night Villas of Distinction booking made by 12/31/22 and departing by 12/31/23. Minimum purchase price of $250 applies. GC is only available to active BJ’s Members and will be emailed to lead guest 6 - 10 weeks after departure. To receive GC, the Membership number must be included on the booking. GC amount is based on the Total Package Price of the booking as seen on your invoice, minus any processing fees and incremental charges such as groceries, pre-paid gratuities or any other additional onsite pre-booked purchases, and after any applicable rebates have been applied. Offer is per booking and is not reflected in advertised prices. GC will be rounded down to the nearest dollar and may have a maximum based on vendor policies. Rewards over $1,200 will be issued through multiple GCs. Offer is not valid on things to do, standalone car rentals or standalone hotel reservations. Offer and participating vendors are subject to change at any time. GC is redeemable only for Membership fees at BJ's Club front-end registers and for merchandise at BJ's Club front-end registers or at checkout at BJs.com. Card is not redeemable at BJ's Gas® locations or on travel purchased through BJ's Travel. US/CA residents only. Additional terms and conditions may apply, please contact a villa specialist for more details.

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Location

Reviews

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

Kirk S.

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.

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.

I wanted to let you know that we arrived home safely and had a lovely trip. The house was beautiful and the staff were all truly great. Shamal is an amazing chef. Michael was the butler and he is a truly kind and compassionate person. I believe it was a "trial" for him to be in this role, so I wanted to put a good word in for him. Could you please communicate that to the owner? Also, Charmaine and Nikki kept the house spotless, and Zeeks maintained the property beautifully. Overall, a great experience. We had a covid scare during our trip (false positive during routine testing) and everyone was exceptionally gracious while we were very stressed and figuring out what to do. I was surprised by the depth of kindness and support that was conveyed by the staff and by the owner as well. Thank you for helping us to arrange a lovely vacation.

Shoshana

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