Windsong

Windsong is an exquisite and very private four-bedroom villa nestled on three acres in the low foothills overlooking Montego Bay’s western coastline. Designed by noted architect Kasimir Coribut, this open-air estate is perfectly positioned to capture Jamaica’s most favorable trade winds along with breathtaking panoramic views to both the east and west. From sunrise over Montego Bay to glowing sunsets stretching toward Negril and the lush hills of Hanover, Windsong offers a truly elevated Caribbean experience defined by serenity, space, and natural beauty.

Windsong is a thoughtfully designed open-air villa that blends the beauty of its natural surroundings into every living space. Airy rooms, soothing water features, and seamless indoor-outdoor flow create an immediate sense of calm from the moment you arrive.

The experience begins at the circular driveway, shaded by a majestic banyan tree adorned with hanging orchids, and continues through a welcoming courtyard filled with tropical plants and gentle fountains. Throughout the estate, lush gardens, rolling lawns, and fruit trees surround the villa, with seasonal produce often finding its way to the breakfast table.

The villa features a 20’ x 40’ private tiled swimming pool with a poolside bar, expansive verandahs for al fresco dining, and inviting gathering spaces for relaxed afternoons and candlelit evenings. Music flows easily throughout the home, both indoors and out, setting the tone for laid-back Caribbean living.

Guests enjoy exclusive access to Windsong and its grounds, including indoor living areas, expansive verandahs, landscaped gardens, the private pool, and poolside bar.

As part of your stay, guests also enjoy complimentary resort membership benefits at the The Tryall Club, subject to availability and club policies. Included access features the beach, non-motorized water sports, tennis courts, 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 may be arranged for a fee and are subject to availability. These may include bar and restaurant dining, spa services, grocery purchases, golf, motorized water sports, tennis shop services, ball boys, and nanny services.

Please note that access to club amenities and services is governed by club policies and availability. On occasion, facilities and guest services may be unavailable due to private events. The Tryall Club reserves the right to modify or update its membership benefits without prior notice.

Whether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape.

Please note that complimentary driver service with a 10-seater van is included on seven-night reservations, with fuel and gratuities at the guest’s expense. Full house reservations are required.

Windsong includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies.

Gratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team.

Beyond just a stay, Windsong offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.