Hanover Windward Garden Villa at the Tryall Club

Caribbean / Jamaica / Montego Bay

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

up to 6
up to 12
Min. Nights Upon Request


  • 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)*


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 are 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. 

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

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

Additional Information

The 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 pros on call. All white attire is required. (Some Tryall Club golf services are subject to a 15% service charge, including green fees, golf cart rentals, and 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 a 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).

Please note: There may be occasions that some or all the facilities for the hotel may be closed for membership guest services due to a private hotel event. The Tryall Club reserves the right to change or alter its membership packages with no advance notice.


6 Bedrooms, 8 Bathrooms

Sleeps 12 Guests

9500 Interior Square Ft.

  • A/C Bedrooms Only
  • Playground Nearby
  • Solar-Heated Saltwater Pool
  • Snorkel Gear
  • Kayaks
  • Butler
  • Assistant Butler
  • Chef
  • Housekeeper
  • Laundress
  • Gardener
  • Tryall Club Membership
  • Hair Dryers
  • Bathrobes
  • Molton Brown Toiletries
  • Air Conditioning
  • Flat-Screen TV
  • Safe
  • Ping Pong
  • Living Room
  • Dining Room
  • Breakfast Room
  • Indoor/Outdoor Dining
  • Private Balconies
  • Soccer Field
  • Flat-Screen TVs
  • Cable Programming
  • Sonos Music System
  • I-pod Dock
  • Sirus Satellite Radio
  • Free Wi-Fi
  • Three Golf Carts
  • Free On-Property Shuttle
  • Great Room
  • Beach
  • Golf
  • Tennis
  • Fitness Center
  • Massage Center
  • Boutique
  • Tryall Market
  • Game Room
  • Kid's Club


Pool Details

Solar-heated saltwater pool

Distance 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

This villa is an open-air property, the bedrooms are the only rooms that have air conditioning

Rates and Availability

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
US $99 Damage Deposit Waiver Fee: A US $99 Damage Deposit Waiver Fee applies to your reservation. It is our goal to ensure that you have a remarkable experience at our villas. And we understand that accidents happen. In lieu of a large security deposit, your reservation will include a $99 Accidental Damage Waiver fee. This will cover accidental damages of up to $2,000 that occur during your stay.

The Tryall Club will collect a security deposit on arrival. If no damage occurs, your security deposit will be refunded and credited to your account. However, if damage does occur, we will reimburse you for any amount which does not exceed US$2,000.
Accidental Damage Waiver
A $99 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
High/Low Season: 5-night minimum stay required

Holiday Season: 10-night minimum stay required

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

Exclusive Offers

Take your vacation to the next level, with 2 free airline tickets.* For a limited time, every reservation over $50,000 will receive an airline reimbursement worth up to $1,000 - any airline, any destination. Imagine flying in style to your handpicked villa located in one of the most beautiful destinations around the world, knowing that you've saved on the cost of your flights. This is your chance to experience the ultimate in luxury travel and indulge in the vacation of a lifetime.

*Free air promotion is valid new bookings only and cannot be applied to existing bookings. Valuation based on two round trip tickets using the bureau of Transportations U.S. average flight price for 2022. Receive up to a $1,000 reimbursement for flights upon presentation of a flight receipt. Minimum booking value of $50,000 applies. The booking value applies to the villa cost only and does not include any additional services or fees. This offer is valid for bookings made 2/20/2023 through 4/02/2023 for travel now through 12/31/2024. Bookings made outside of this period will not be eligible. The $1,000 air credit offer is non-transferable, has no cash value, and cannot be redeemed for any other service. The airline credit will be applied to your booking once your villa rental has been paid in full. The airline credit will be redeemed by providing a receipt of your booked flight and a check will be sent to you within 15 business days of providing flight documentation. All offers are subject to availability. We reserve the right to modify or cancel this promotion at any time without notice.



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.


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