Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay.
Welcome to Windsong represented by EXCEPTIONAL VILLAS, the world's leading villa rental company on Trust Pilot. This truly luxurious 4 bedroom private villa just minutes from the exclusive Tryall Club in Montego Bay. Originally designed by world-famous Kasimir Coribut, the villa benefits from its prime location with spectacular views day and night and the most favourable trade winds. The east side captures the sunrise and Montego Bay, and the west side is an equally lovely vista of Round Hill, the sea and the sunset. The grounds are like a park ~ plentiful with tropical trees bearing almond, coconut, lime, avocado, orange, ackee, breadfruit, fig and papaya and adorned by brilliant hibiscus and bougainvillaea. Five fountains grace the indoor gardens. From the central fountain, stone walkways lead to the Great Room, inside the dining room, bedrooms and bar - and the wonderful 700-square-foot veranda with its casual alfresco dining area overlooking the pool. Interiors are beautifully designed in white, bright chintz, glass sculpture, fanciful hand-painted chandeliers and wonderful objets d’art. Floors are cut stone, terrazzo and marble. Table service is Italian, French porcelain or Wedgwood. All rooms are distinguished by a remarkable art collection, including many Haitian oils (Bottex, Saul, etc.) and sculptures. Completing this home are the lovable pets - three happy dogs who occasionally take a drink from the pool, roam the yard but never enter the villa. Windsong can be rented for larger groups with its neighbouring villas, Hanover House and Goat Hill ~ each within walking distance ~ for a compound of 13 bedrooms, 3 swimming pools and 19 staff including 3 cooks. This is a convenient and excellent combination for wedding parties and family reunions. When you stay at Windsong, you will be personally cared for by The Villa’s own cook, butler, housekeeper, gardeners, and laundress.
BEDROOMS: Primary Bedroom: Queensize bed; en-suite bathroom, double vanity, bathtub and separate shower. DSL Internet access, TV, Bose Wave Radio/CD. Two private balconies. Magnificent ocean views day and night. Bedroom 2: Kingsize or twin beds at guests’ option; en-suite bathroom with tub-shower combination. Sony radio/cassette/CD player. Private balcony. Magnificent view. Bedroom 3: Kingsize or twin beds at guests’ option; en-suite bathroom with tub-shower Combination. Radio/cassette/CD player. French doors to private terrace and ocean view. Bedroom 4: Kingsize or twin beds at guests’ option; en-suite bathroom with tub-shower combination. Radio/cassette player. French doors to private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults
AMENITIES • 4-bedroom deluxe private villa on 3 acres ~ spectacular ocean views east and west - private tennis court - 20’ x 40’ private tiled pool and poolside bar • Staff: cook, butler, housekeeper, gardeners, laundress - complimentary driver included in full house rentals (4 bedrooms) & 7-night minimum stay. Guests are responsible for all petrol & gratuities - 32” Sony Trinitron Direct TV and sound system ~ library of movie DVD’s & music CD’s - high-speed DSL Internet access ~ also a fax machine
TRYALL CLUB MEMBERSHIP All guests must pay a resort entry fee of US$34 per person per day, plus a 15% tax, to have access to the resort amenities at the Tryall Club. Children 13-15 years of age pay a discounted rate of 50% off, plus 15% tax, and children 12 & under are complimentary. Complimentary amenities include the beach, non-motorized water sports, tennis, gym, Hummingbird Kids Club, Great House afternoon tea, Manager's Cocktail Party, and various special events. Membership is guaranteed for guests traveling through November 30, 2026. On occasion, some or all the facilities of the hotel may be closed due to a private hotel event. Tryall Club reserves the right to alter its membership packages with no advance notice. Pricing is subject to change without notice
Our prices include all fees. No hidden fees.
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This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Montego Bay
Located in Montego Bay, this villa is next to a golf course. Bellefield Great House and Gardens and Creek Dome are local landmarks, and some of the area's activities can be experienced at Tryall Golf Club and Chukka Ocean Outpost at Sandy Bay. Rocklands Bird Sanctuary and Widowmaker's Cave are also worth visiting. Fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and mountain climbing nearby.
Montego Bay Cruise Ship Terminal - 13 min drive - 14.0 km
Getting around
Montego Bay (MBJ-Sir Donald Sangster Intl.) - 29 min drive
Restaurants
Montego Bay Yacht Club - 15 min drive
Piano Bar - 15 min drive
Oceana - 15 min drive
Altitude Bar - 14 min drive
Sky Beach - 7 min drive
Frequently asked questions
Is Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay. pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay.?
As of 1 Apr 2026, prices found for a 1-night stay for 2 adults at Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay. on 22 Jun 2026 start from £957, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay.?
Check-in begins at 3:00 PM.
What time is check-out at Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay.?
Checkout is at 11:00 AM.
Where is Luxurious 4 bedroom private villa close to Tryall Club in Montego Bay. located?
Situated in Montego Bay, this golf villa is within 9 miles (15 km) of Tryall Golf Club, Fairview Shopping Center and Rocklands Bird Sanctuary. Westgate Shopping Centre and Bellefield Great House and Gardens are also within 9 miles (15 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We had the most amazing time at the Windsong Villa. The home, views and staff were perfect for our group. I couldn't have imagined a more perfect setting to celebrate my birthday with my family. We also enjoyed a family photoshoot at the Round hill resort. It was all very magical!
Tashelle Darby T.
From a partner site
10/10 Excellent
Ksenya Wong K.
11 Sept 2023
The Most Amazing Time!
My family's trip to the Windsong Villa was a blast! We were greeted by cool towels and warm smiles. Every meal was special; Chef Aldene is an AMAZING cook! My favourite part was the view. It was nice to watch the sun rise from the back of the villa. There was amazing service and I really loved all of the different napkin rings they used. Celebrating birthdays here was a blast and it warmed everyone's hearts Everyone put so much love and hard work into keeping this place alive and beautiful. It was made my trip special and I hope it does the same for many others.
Ksenya Wong K.
From a partner site
10/10 Excellent
Leretha Farley L.
28 Jul 2023
Great!
We enjoyed each day at Windsong. The staff were great and DJ made sure we had it all!
Leretha Farley L.
From a partner site
10/10 Excellent
TASHELLE DARBY T.
10 Jul 2023
It was a blast!
My family's trip to the Windsong Villa was a blast! We were greeted by cool towels and warm smiles. Every meal was special; Chef Aldene is an AMAZING cook! My favourite part was the view. It was nice to watch the sun rise from the back of the villa. There was amazing service and I really loved all of the different napkin rings they used. Celebrating birthdays here was a blast and it warmed everyone's hearts Everyone put so much love and hard work into keeping this place alive and beautiful. It was made my trip special and I hope it does the same for many others.
TASHELLE DARBY T.
Archival
10/10 Excellent
Yelverton Y.
14 May 2015
Everything about it exceeded our expectations.
Dear Emma,
Thank you so much for recommending Windsong as our vacation villa. Everything about it exceeded our expectations. The house itself is divine. The rooms are all decorated with the utmost taste and elegance while maintaining a relaxed atmosphere. We loved the layout of the villa and enjoyed using all of the rooms. We had several options for dining and several areas for lounging or playing cards. Our views were outstanding, and we found that the location is the perfect combination of privacy and convenience. The membership to use the facilities at Roundhill did make a huge difference as their beach and food are unparalleled. The bedrooms and bathrooms were all updated, spacious, and very comfortable.
As for the staff at Windsong, please pass along to them our deepest gratitude. The children loved Christine, and she made special efforts to do things like braid their hair - a favorite treat for the girls. DJ always had a smile and seemed to appear out of the blue at just the right moment. He knew what we wanted before we did! Our head housekeeper kept everything immaculate, and the night watchman was discreet but also very helpful and kind. We never felt crowded or uncomfortable having full time help. They all worked incredibly hard while also giving us privacy and space. It was a perfect balance that I believe is very rare.
A special thanks goes to Ra'shan, our superb chef. We initially planned to eat out several nights, but found that we so enjoyed our meals at the villa we didn't want to go out. He was incredibly accomodating - serving the children first with a simple meal and allowing the adults to eat a bit later. Everything he cooked was divine. We particularly enjoyed his pumpkin soup, roast chicken, collard greens (we requested those several times), and peas and rice. He expertly prepared fish that the men caught on a trip, and he even hand decorated a birthday cake. His skills are limitless. Each meal also included a unique table setting, and we marveled at the variety of fun napkins and table accessories that appeared each day. It was just another detail that made the whole trip and home so special.
Truly, we were so pleased with the villa that we only left for a few day trips to the beach.
I would recommend the property to anyone who enjoys privacy and luxury while traveling. It is wonderful for families with older children traveling together and would also be a perfect adult only getaway. I would not advise use of the villa for families with children who can not swim or are too young to follow directions. The open air layout is glorious, but the pool is accesible at all times and would not be safe for a young child. We traveled with a three year old who follows directions very well, but we still took the precaution of closing and locking all of the doors to the pool at night. The bedrooms open into the main areas and there is not a way to keep children from roaming.
We loved everything about Windsong and plan to stay there many more times.
Again, Emma, thank you so very much and please relay our accolades to the lovely ladies and gentlemen who work at Windsong as well as to the owner who has cultivated a spectacular property.
Yelverton Y.
Archival
10/10 Excellent
Collins C.
24 Mar 2015
It was absolutely amazing!
Hi Emma,
It was absolutely amazing! We all had such a great time, and will surely be back as soon as possible:)
We have no complaints whatsoever!
Thank you for all your help.
Collins C.
Archival
10/10 Excellent
Saulnier S.
23 Mar 2015
I have recommended the house to everyone I know!
Hi Emma, I demand a free second week:) If you saw our reaction when we walked into the villa it would have been worth more than a thousand words! In all honesty it was the best vacation I have had since my first daughter was born about 7 years ago. The staff was amazing and had great intuition for what we needed. They were like ninjas quietly swooping in at exactly the right moment to close up the house, or make coffee. And the environs were simply stunning! The layout of the house was perfect and the grounds/view were impeccable. I have recommended the house to everyone I know. I will carry these moments with me forever. We will be in touch to plan another vacation for certain! Thank you so much for all of your help coordinating the trip!