Low Season Rates Starting At $1,715.00 a night
9500 sqft
** Please drop us a message before booking the property as we need to check availability for all requests at this villa **

, Montego Bay, Jamaica

Windward is aptly named for the continuous cross current of trade winds that traverse the property. This fabulous 6-bedroom home has lovely views from every room and from both levels. Airy and light interiors, large, well-configured bedrooms, and furnishings that mix traditional Jamaican with contemporary make this villa a relaxing haven.

The villa looks out from an elevated location on Mahogany Drive and is built in classic Caribbean style, on two levels with spacious and contemporary interiors cleverly designed for family living. It looks down over a very well landscaped garden that contains many interesting trees and shrubs. The energetic will enjoy the stroll to the tennis courts and gym whilst the golf course is only a short golf cart ride away.

Windward’s four bedrooms on the upper level enjoy terraces that face the ocean and the two lower level bedrooms open onto patios with views of the stunning gardens. There are two master suites each with king-sized Mahogany beds, private dressing rooms, and en suite bathrooms finished with floor-to-ceiling travertine tiles, marble double vanities, walk-in showers, and deep bathtubs. There is a guest bedroom adjacent to each master suite. One has a king-size bed and the others have twin beds that can be configured as a king if required. The guest en suite bathrooms have walk-in showers.

The relaxing, free-flowing, and spacious living room, dining room, and breakfast room are all on the main level with magnificent ocean views. An open plan design facilitates easy living and the colorful fabrics and comfortable furnishings give a spirited feel accented with a well-curated art collection. Dinner on the great veranda – and the chef here is truly talented – makes for a spectacular occasion with views across Sandy Bay and the city of Montego Bay in the distance.

The villa’s lower level comprises a Comac heated infinity saltwater swimming pool which can be lit at night. The covered veranda on this level features a family area with a ping pong table and other games, while the garden includes a small soccer field for family football matches.

Can be rented as 4 and 6 Bedroom.

• (Comac) infinity, lit, solar heated saltwater pool – deepest point 6 feet 6 inches
• Indoor/Outdoor Dining
• Private balconies
• Football field
• Molton Brown toiletries and Hair dryers
• Free Wifi
• Cable Flat screen TVs
• Sonos music system
• Safes and I-pod dock
• Sirius Satellite Radio
• 3 golf carts
• Free on-property shuttle service

• Short distance to tennis
• Massage center and Fitness center
• Boutique and Tryall market
• Games room and Kid’s Club
• Golf and  Beach

• Chef
• Butler
• Assistant Butler
• Laundress 
• Housekeeper
• Two Gardeners

Main Level Bedrooms
Bedroom 1 - King-size bed, A/C, Toilet, En-suite bathroom, sunken bathtub and separate Walk-in shower
Bedroom 2 - King-size bed, A/C, Toilet, En-suite bathroom with Walk-in Shower
Bedroom 3 - King-size bed, A/C, Toilet, En-suite bathroom, sunken bathtub and separate walk-in shower.
Bedroom 4 - King-size bed, A/C, Toilet, En-suite bathroom, Walk-in Shower
Lower Level Bedrooms
Bedroom 5 - 2 Twin beds (which can be combined as kings), A/C, En-suite bathroom, garden
Bedroom 6 - 2 Twin beds (which can be combined as kings), A/C, En-suite bathroom, garden

Tryall Club Temporary Membership Dues
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 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. The Tryall Club reserves the right to change or alter its membership packages with no advance notice.
King Size
King Size
King Size
King Size
Single/Twin Size
Single/Twin Size
Single/Twin Size
Single/Twin Size

Onsite Services:

  • Massage
  • Chef
  • Housekeeper
  • Staff

Local Features:

  • Fitness Center


  • Game Room
  • Satellite/Cable TV


  • Outdoor Pool
  • Private Pool
  • Heated Pool


  • Hair Dryer
  • Internet
  • Washer
  • Parking
  • Air Conditioning
  • Safe
  • En-Suite Bathrooms
  • Shower
  • Dining Table


  • Luxury
  • Family
  • Sports/Activities
  • Tourist Attractions
  • Adventure


  • Balcony
  • Outdoor Dining
  • Terrace

Attractions & Activities:

  • Kayaking
  • Swimming
  • Optional Golf
  • Tennis Court



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  • All rates quoted in USD.
  • Please inquire for per bedroom rates for less than maximum occupancy.
  • Rates are subject to change without notice
  • Thanksgiving may be charged at a higher rate.

Fee Amount
Damage Waiver Fee $79.00
Service Fee 5%
Tax 10%

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