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Ready for a family vacation? The fun begins and ends with finding the right place to stay. Windward Villa in Montego Bay is just right for a family or group of friends. There are a total of six bedrooms, each of them with its own bathroom. Lots of amenities will be found here that you won't find in other vacation spots. The beach is a short five-minute drive, which is especially great if you take the kids with you. The villa has both a kitchen and BBQ area, but you may want to eat out, too, and some of the best restaurants are only a few minutes' drive away. If you want to explore the area around you, you even have the option of using a golf cart! The staff is very helpful and will be happy to accommodate your needs. Windward Villa is a terrific destination for a family vacation.

Shawna , 214-350-6220 x9102

Classic Caribbean Villa on Mahogany Drive

Windward is aptly named for the continuous cross current of trade winds that traverse the property. This graceful 6 bedroom home has the most spectacular 180 degree views from every room and from both levels. Airy interiors, well configured bedrooms and chic furnishings with eclectic accents make this villa a relaxing haven.

The villa looks out from the crest of the hill on Mahogany Drive and is built in classic Caribbean style, on two levels with spacious and contemporary interiors cleverly designed for family living. Windward’s four bedrooms on the upper level enjoy terraces which 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 which can be configured as a king if required. The guest en suite bathrooms have walk-in showers.

The relaxing 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 colourful fabrics and comfortable furnishings give a spirited feel. Beautiful modern kitchen with new appliances allows gourmet meal preparation, and dinner on the great verandah 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 verandah on this level features a family area with ping pong table and other games, while an expansive yard includes small soccer field for family football matches.

The villas’ staff comprises a Chef, Butler and Assistant, Housekeeper, laundress and Gardener.

Master Bedrooms 1, 3, and 5: King-size 4-poster mahogany bed, 32-inch flat screen TV with access to cable, mahogany, Double French doors to veranda and sea view. Large en-suite dressing room and bathroom with marble double-basin vanity, deep bathtub, and separate walk-in shower.

Bedroom 2: Two twin 4-poster beds, 26-inch flat screen with cable television, French doors to small balcony and ocean view; en-suite bathroom with single-basin vanity and walk-in shower.

Bedroom 4: Twin beds, 26-inch flat screen with cable television, French doors to small balcony and ocean view; en-suite bathroom with single-basin vanity and walk-in shower. All twin beds can be converted to king at your request.

Bedroom 6: King bed, 26-inch flat screen with cable television, French doors to small balcony and ocean view; en-suite bathroom with single-basin vanity and walk-in shower.

(Twin bedrooms can be converted to kings with advanced notice).

Amenities:

Air-conditioned bedrooms

Ceiling fans

Four acres of lawn, gardens, pond, and coconut trees

Barbecue

Six TVs (flat screens)

DVD

CD player

Wireless Internet

Child friendly

Large lawn

32-foot by 17-foot private pool (salt chlorinator) heated with solar panels

iPod docking stations, robes, hair dryers

FACILITIES:

Complimentary golf cart for transportation within the resort as well as a scheduled shuttle service around the estate.

Six cable televisions

DVD Player

Internet access (bring your own laptop)

iPod docking stations in each bedroom

Magnificent views of the Caribbean sea

Large private pool

*Special Holiday weeks, e.g. Thanksgiving may be charged at Premium rate.

Dates People Nightly
Nov 25, 2018 to Dec 17, 2018
7 Night Minimum
1-12 people $1,624 USD
Dec 18, 2018 to Jan 5, 2019
7 Night Minimum
1-12 people $3,896 USD
Jan 6, 2019 to Apr 26, 2019
7 Night Minimum
1-12 people $2,922 USD
Apr 27, 2019 to Nov 22, 2019
7 Night Minimum
1-12 people $1,624 USD
Nov 23, 2019 to Nov 30, 2019
7 Night Minimum
1-12 people Rates Upon Request
800-869-8017
Dec 1, 2019 to Dec 17, 2019
7 Night Minimum
1-12 people $1,624 USD
Dec 18, 2019 to Jan 4, 2020
7 Night Minimum
1-12 people $3,896 USD

Notes on Rates:

  • All rental rates are based on two persons per bedroom.
  • This property charges rates in US Dollars (USD).
  • Rates do not include: tax of 10%, island charges of 5%.
  • Rates are subject to change.
Rates shown in

Choosing the right villa is just the first step in creating the perfect vacation experience. We help you plan every element of your villa vacation, from rental cars to spa treatments, completely personalized to you.

  • spa services
  • chef/cook services
  • butler service
  • car rental
  • restaurant reservations
  • activity and sightseeing
  • ferry/airport transfers
  • grocery provisioning
  • laundry service
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Calendar last updated Wed, Dec 12, 2018 5:58 pm.

    Beds & Baths

    Main House

    • Bedroom 1: Upper Level
      • 1 King, Air Conditioning, Ceiling Fan, TV, Ocean View, Exterior Access, Terrace/Balcony
      • Ensuite Full Bath with Shower, Two Sinks, Tub
    • Bedroom 2: Upper Level
      • 1 King, Air Conditioning, Ocean View, Terrace/Balcony
      • Ensuite Full Bath with Shower, Two Sinks, Tub
    • Bedroom 3: Upper Level
      • 1 King, Air Conditioning, Ocean View, Terrace/Balcony
      • Ensuite Full Bath with Shower
    • Bedroom 4: Upper Level
      • 1 King, Air Conditioning, Ocean View, Terrace/Balcony
      • Ensuite Full Bath with Shower
    • Bedroom 5: Lower Level
      • 1 King/Twin, Air Conditioning, Garden View, Terrace/Balcony
      • Ensuite Full Bath with Shower
    • Bedroom 6: Lower Level
      • 1 King/Twin, Air Conditioning, Garden View, Terrace/Balcony
      • Ensuite Full Bath with Shower

Staff

  • 1 Chef
  • 1 Laundress
  • 1 Housekeeper
  • 1 Housekeeper
  • 1 Gardner
  • 1 Gardner
  • 1 Butler

Features

  • Balcony
  • Bathtub
  • BBQ Outside (Gas)
  • Blender
  • Cable TV
  • CD Player
  • Ceiling Fans
  • Coffee Maker
  • Dishwasher
  • Docking Station
  • DVD Player
  • Family
  • Fridge
  • Golf Cart(s)
  • Golf Nearby
  • Great Views
  • Group
  • Hair Dryers
  • Heated Pool
  • Ice maker
  • Internet Access/WiFi
  • Iron/Ironing Board
  • Microwave
  • Oven/Stove
  • Pool at Villa
  • Private
  • Resort Fitness Facilities
  • Resort Villas
  • Safe
  • Satellite
  • Short Walk to Beach
  • Television
  • Tennis Nearby
  • Toaster
  • Water Sports Nearby
  • Wedding
Pool Infinity, heated saltwater pool
Air Conditioning A/C in bedrooms
Location Montego Bay, Jamaica
Staff Staff Total: 7
  • 1 cook
  • 1 laundress
  • 2 maids
  • 2 gardners
  • 1 butler
Beach About a 5 minute drive by golf cart to the Tryall Club private, 1,000-yard sandy beach
Groceries 10 Mins. walking, 5 Mins. by car
Restaurants 10 Mins. walking, 5 minutes by car
Transfers Airport transfers can be arranged for this villa (guest expense). The Tryall Club is located 12 miles west of Montego Bay or 20 minutes west of the Sangster International Airport. Another popular way to get around is to hire a private driver and air conditioned minivan for the week. This will include your airport transfers and is a great way to go sightseeing in Jamaica. Your driver will be your tour guide, and is sometimes the best source of local information. Inquire for rates.
Notes Dining room seats 10
Included Free shuttle service to nearby Tryall club locations
Children Welcome
Additional The Club requires all guests to become members during their stay via a Temporary Membership Fee of $149.50 per week + 15% service for each person over the age of 16 or $26 + 15% service per person per day for stays of less than 7 days. Gratuity is expected for the staff at approximately 10% in the high season, and 15% in the low season. Please plan to pay your staff in cash.

Guests are responsible for purchasing the groceries.
Availability and usefulness of sports and outdoor equipment is not guaranteed because of heavy use and exposure to the elements.