Windsong

Villa Overview

• 4-Bedroom deluxe private villa on 3 acres ~ spectacular ocean views east and west
• Open-air villa
• 20’ x 40’ Private tiled pool and poolside bar
• Complimentary driver & 10-seat van on 7-night reservations (gas & gratuities are additional costs). Full house required.
• Full staff: butler, chef, housekeeper, gardeners, laundress
• Brand new  55“ UHD Samsung  6 Series TV ~ library of movie DVDs and music CDs
• Wi-Fi
• All bedrooms have air-conditioning, fans, safes, robes, and bathroom amenities
• Complimentary crib & highchair
• Glorious trade winds, breathtaking sunrises, and sunsets

Windsong is a luxurious 4-bedroom private villa retreat nestled in the low foothills overlooking Montego Bay’s western coastline. 

This charming tropical villa encapsulates a complete Jamaican experience. Noted for its sweeping panoramic views, airy rooms, lush rolling landscape, and well-laid-out tropical gardens, Windsong Villa is itself simply gorgeous and exquisitely inviting – from the outside in. 

The home and its elegant features cleverly blend the beauty of nature into the indoor settings, and guests get an instant sense of serenity upon arrival. 

The Windsong experience begins the moment you turn onto the circular driveway, shaded by our majestic banyan tree - resplendent with hanging orchids - and continues as you enter the welcoming courtyard, filled with vibrant tropical plants and water fountains that invite you to enjoy the finest aspects of Caribbean living. 

Windsong’s unique hill, located on the outskirts of Montego Bay, is perfect for marveling at the stunning views while enjoying the favorable trade winds of the season. The east view captures the rising sun over Montego Bay, while to the west is an equally lovely vista of Round Hill and breathtaking tropical sunsets above the lush green hills of Hanover. 

With soothing water features throughout, you will feel instantly welcome and at home. The well-cared grounds are thoughtfully filled with a variety of local tropical trees, plants, and flowers, and fruit trees – the produce of which make it to the breakfast table when in season. Wander at leisure through this extensive garden and get to know Jamaica’s flora. 

The villa is managed by a highly experienced team of staff who will ensure that your stay here meets and exceeds your expectations. The team will be happy to offer suggestions and recommendations when asked. 

Plan your meals with the skillful, creative chef who will work with your tastes and dietary needs – serving up meal after sumptuous meal made from the freshest of ingredients, for your culinary delight. 

You may wish dinner to be served by candlelight indoors or in the more casual al fresco dining area on the verandah overlooking the pool. The poolside bar is kept stocked with ice and drinks for your convenience, and the sound system supplies music both indoors and out. 

Accommodations

All bedrooms are 225 square feet in size and have state-of-the-art remote control quiet air conditioners.

Main Level

Master Bedroom
Queen-size bed; en-suite bathroom, double basin vanity, bathtub, and separate shower. DSL Internet access, Bose Wave Radio/CD. Two private balconies. Magnificent ocean views day and night.

Bedroom 2
King-size or twin beds at guests’ option; en-suite bathroom with tub-shower combination. Sony radio/cassette/CD player. Private balcony. Magnificent view. 

Lower Level

Bedroom 3
King-size or twin beds at guests’ option; en-suite bathroom with tub-shower Combination. Radio/cassette/CD player. French doors to a private terrace and ocean view.

Bedroom 4
King-size or twin beds at guests’ option; en-suite bathroom with tub-shower combination. Radio/cassette player. French doors to a private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults.

Tryall Membership

A special amenity available to guests in this villa is its complimentary membership with The Tryall Club, extending until November 30, 2026. This membership enhances your stay with exclusive access to The Tryall Club's prestigious amenities and services. Enjoy a wealth of luxurious offerings and unforgettable experiences during your time at Windsong.

Please note: Members enjoy access to a wide range of Club facilities and experiences, with many amenities included at no additional charge. Complimentary offerings feature the beach, non-motorized water sports, tennis, a well-equipped fitness center, the Hummingbird Kids Club, Great House afternoon tea, the Manager’s Cocktail Party, and a variety of special events throughout the year.

Additional services and experiences are available for a fee, including the tennis shop, ball boys, bar and restaurant dining, spa services, grocery purchases, motorized water sports, nanny services, and golf. 

Additional Information

Windsong Menu