Stay 5 Nights, Pay for 4
Windsong Villa stands as an impeccably designed and secluded residence, mere minutes away from Montego Bay's famed Round Hill estate.
This enchanting tropical villa embodies the essence of Jamaican living. Renowned for its expansive vistas, breezy interiors, verdant surroundings, and meticulously landscaped gardens, Windsong Villa emanates beauty and warmth, captivating from the exterior to the interior.
Blending seamlessly with its natural surroundings, the villa welcomes guests with an immediate sense of tranquility as they traverse the circular driveway shaded by a magnificent banyan tree adorned with hanging orchids. The courtyard beckons with its lush foliage and bubbling fountains, inviting guests to immerse themselves in the epitome of Caribbean lifestyle.
Perched atop a hill on the outskirts of Montego Bay, Windsong offers unparalleled views, allowing guests to marvel at the sunrise to the east over Montego Bay and relish in the breathtaking sunsets to the west above Round Hill and the verdant hills of Hanover, all while being caressed by the gentle trade winds.
Throughout the villa, soothing water features abound, creating an atmosphere of serenity and hospitality. The meticulously tended grounds showcase a rich variety of indigenous flora and fruit trees, the bounty of which graces the breakfast table when in season, inviting guests to leisurely explore Jamaica's botanical treasures.
Expertly managed by a seasoned team, Windsong ensures an experience that surpasses expectations. From personalized meal planning with the creative chef to attentive service and thoughtful recommendations, every aspect of your stay is meticulously curated for your utmost enjoyment.
Indulge in candlelit dinners indoors or opt for the relaxed ambience of the al fresco dining area overlooking the pool, where the poolside bar is always stocked with refreshing drinks and the sound system sets the mood for both indoor and outdoor gatherings.
The Tryall Club 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.
Bedroom 1: Main floor Master bedroom with a queen-size bed, A/C, TV, sound system, balconies and en-suite bathroom with bathtub, shower, double vanity and WC. 2 guests maximum.
Bedroom 2: Main floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, balcony and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
Bedroom 3: Lower floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, private terrace and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
Bedroom 4: Lower floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, private terrace and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include
While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.
Plan your dream destination wedding or special Caribbean event. The villa is available for wedding receptions and special events.
Maximum guests: 50 guests
Rental rates:
The villa requires seven nights minimum rental of villa at the full house rental rates. A $30 per person surcharge applies to outside guests (over double occupancy per bedroom) who attend a rehearsal dinner, the wedding reception, brunch, or any other hospitality event at the wedding villa.
Clients are also required to hire outside caterers as well as rent chairs, tables, tents, glasses, cutlery, and crockery.
Terms and conditions:
The villa does not allow unregistered guests to stay overnight. Overnight guests are restricted to 2 guests per rented bedroom and must be declared. If extra guests require accommodations, we recommend the rental of neighboring "sister" villas. For "sister" villas where additional guests are accommodated, there is a seven-night minimum in High Season and a five-night minimum in Low Season. Guests are responsible for the set-up and clean-up of the event. The event may not occur within 24 hours of departure. For example, with a Saturday departure guests must hold the event on Thursday or sooner.
Please contact our villa specialists to assist you in selecting the perfect wedding venue for your special occasion.
Windsong is offering a 5th night free for travel between April 16, 2026 and December 15, 2026.
Promotion applies to the 2,3 bedroom rate category.
This special offer does not include a complimentary driver
Blackout Dates: November 20, 2026 - November 27, 2026Earn up to a US$500 concierge credit on qualifying bookings
The Endless Summer Escape applies to all new reservations booked between May 12 and August 31, 2026.
Terms and conditions
Credit is based on total booking value before taxes and fees. Credit applies to experiences only and cannot be used toward villa rental, taxes, or fees. Credit must be used during the booked stay and expires at checkout. Cannot be combined with other offers and has no cash value. Valid only on new reservations made within the booking window. Concierge service must be booked directly through our website and does not apply to third-party providers or external websites.
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