• Toll Free(US/CANADA):1 800 245 5109
  • LoCall (UK):0845 528 0209
  • Phone:+353 1 513 4197




Welcome to Windsong, a truly luxurious 4 bedroom private villa just minutes from the exclusive Round Hill 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.

The Great Room is a stunning free-standing pavilion with 22 glass doors that open to the east and west to the vast ocean views. The sound system carries music to indoor and outdoor living areas. The poolside bar is always stocked with ice and drinks.

The excellent hard-surface tennis court is maintained perfectly by Davis Cup/Wimbledon pro-Richard Russell. 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.
For larger groups, Windsong can be rented with its neighbouring villas, Hanover House and Goat Hill ~ each within walking distance ~ for a compound of 13 bedrooms, 3 swimming pools, 2 tennis courts and 19 staff including 3 cooks. This is a convenient and excellent combination for wedding parties and family reunions.

Check out more of our beautiful Wedding Villas in Jamaica here.

STAFF When you stay at Windsong, you will be personally cared for by The Villa’s own cook, butler, housekeeper, gardeners, and laundress. You will feel welcomed and pampered throughout your stay. The staff will be on hand to look after your every need and ensure your comfort at all times.

The Bedrooms

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

Main Level
Master Bedroom
Queensize bed; en-suite bathroom, double basin vanity, bathtub and separate shower. DSL Internet access, television, 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.

Lower Level
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 a private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults.


• 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
• full staff: cook, butler, housekeeper, gardeners, laundress
• 32” Sony Trinitron Direct TV and sound system ~ library of movie DVD’s and music CD’s
• high-speed DSL Internet access ~ also a fax machine
• glorious trade winds, breathtaking sunrises and sunsets
• Round Hill membership: complimentary beach, two connecting heated pools for parents & children, jogging trail, Manager's Cocktail Party. For various fees: Pineapple Kids Club, fitness room, tennis, hair salon & spa, bars & restaurants, gift shops, water sports, Internet room, beach parties Mon-Wed-Fri
• The Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, new Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, beach parties Mon-Wed-Fri

Villa Features

• 4 Bedrooms, 4 Bathrooms
• Sleeps 8 People
• 5 Staff
• Air Conditioning
• Children Welcome
• Fully Staffed Villa
• Golf Available Tryall Club. Across town: White Witch, Cinnamon Hill, Half Moon
• Handicap Access
• Internet Wireless
• Pool
• iPod Dock(s)
• Sirius or XM Radio
• Bathrobes
• Hair Dryers
• Round Hill member
• Tryall Club member
• Kids Club Membership
• Complimentary Calls to the US, UK and Canada
• Wireless Internet Access
• Full Gym Nearby (walk, drive or take golf cart)
• Golf on Site or Nearby
• Private Tennis Court
• Available for Weddings
• Handicap Accessible
• Spa on Site or Nearby


Area description

Windsongs surroundings certainly won't disappoint as its located in one of the most beautiful areas in Jamaica- Montego Bay. Enclosed by a cradle of hills with stunning views of the western coastline, Montego Bay’s lovely beaches are just one of the reasons why it is so popular. Montego Bay is a busy place with the centre of activity centred along Gloucester Avenue which has been renamed the “Hip Strip”, bars, restaurants and gift shops line most of the avenue. The strip ends with the infamous Margaritaville and soon after this you will come to Montego Bay’s most famous beach called Doctor’s Cave Beach. At the end of the hip Strip, the sea emerges once again with a lovely stretch of beach with some great snorkelling.
Downtown Montego Bay is not touristy but great to visit if you want to get a flavour of local Jamaican culture.

• Beach: 4 minutes to Round Hill, 11 minutes to the Tryall Club
• Town: 20 minutes via driver
• Airport: 20 minutes


Montego Bay
Nearest airport Montego Bay Airport
17.5 km
Nearest beach Round Hill 800 meters

Accommodation, Facilities and Services

  • Bedroom(s): 4 ( Sleeps 8 )
    2 Double with en-suite, 2 Twin with en-suite
  • Bathroom(s): 4
    4 Baths, 4 Showers, 4 Wash basins, 4 Toilets
  • General facilities: Balcony / Deck, Garden View, High Speed Internet, Panoramic Views, Pool, Private Location, Private Terrace, Security, Terrace, Wifi
  • Indoor facilities: Air conditioning, All Bedrooms Air Conditioned, All Bedrooms En Suite, CD Player, DVD Player, iPOD Docking Station, Luxury Finishes, Media Room, Phone, TV
  • Outdoor facilities: Deck/Decking, Enclosed Garden, Patio, Private Terrace, Restaurants nearby, Sea Views, Sun Loungers, Sun Umbrellas, Swimming pool
  • Services: Cleaning inclusive, Concierge Service, Linen provided, Maid service, Personal Chef Included, Towels provided
  • Access: Off-road parking


  • Local activities: Climbing, Cycling, Fine Dining, Fishing, Golf, Horse riding, Shopping, Swimming, Tennis, Walking, Water Sports


Show Full Calendar Hide Calendar
July 2020
August 2020
September 2020
October 2020
November 2020
December 2020
January 2021
February 2021
March 2021
April 2021
May 2021
June 2021
  • Booked
  • Available
  • Pending


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
19-Apr-2020 - 20-Nov-2020
Nightly rate Weekly Min. Stay Change-over
$ 929 $ 6,503 5 Nights -
21-Nov-2020 - 28-Nov-2020
Nightly rate Weekly Min. Stay Change-over
$ 1,207 $ 8,449 7 Nights -
29-Nov-2020 - 14-Dec-2020
Nightly rate Weekly Min. Stay Change-over
$ 929 $ 6,503 5 Nights -
15-Dec-2020 - 18-Dec-2020
Nightly rate Weekly Min. Stay Change-over
$ 1,557 $ 10,899 7 Nights -
19-Dec-2020 - 26-Dec-2020
Nightly rate Weekly Min. Stay Change-over
$ 1,700 $ 11,900 7 Nights -
27-Dec-2020 - 02-Jan-2021
Nightly rate Weekly Min. Stay Change-over
$ 1,843 $ 12,901 7 Nights -
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 929 - $ 1,843 $ 6,503 - $ 12,901 5 Nights -
19-Apr-2020 - 20-Nov-2020 Low Season 2020 $ 929 $ 6,503 5 Nights -
21-Nov-2020 - 28-Nov-2020 Thanksgiving 2020 $ 1,207 $ 8,449 7 Nights -
29-Nov-2020 - 14-Dec-2020 Low Season 2020 $ 929 $ 6,503 5 Nights -
15-Dec-2020 - 18-Dec-2020 High Season 2020 $ 1,557 $ 10,899 7 Nights -
19-Dec-2020 - 26-Dec-2020 Christmas 2020 $ 1,700 $ 11,900 7 Nights -
27-Dec-2020 - 02-Jan-2021 New Year 2020 $ 1,843 $ 12,901 7 Nights -


Everything about it exceeded our expectations.
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.

By Yelverton for a stay in Mar, 2015
It was absolutely amazing!
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.

By Collins Party for a stay in Mar, 2015
I have recommended the house to everyone I know!
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!

By Saulnier Party for a stay in Mar, 2015

See what our experts have to say about this property.

Special Offers
  • Get in Touch

    Ask us about our special offers

    Contact Us
  • Join Our Mailing List

    Get offers sent direct to your mailbox

    Receive Offers

Expert Reviews

The Veiws!

Expert Review Pic This is a great villa for a group of friends or a family. The pool area is great, loads of space and a very generous pool. I love the amazing ocean views in the distance. There is a plenty of spaces to relax and unwind and have a great vacation!

By From Exceptional Villas

Inquire About Villa

  • Name is required.
    An email address is required.
  • Try using numbers only
  • We need travel dates
    We need travel dates
    Some of the dates you have selected are already booked. Please try again.

Our team know each destination and every villa we feature.

We also offer a personalized and fully complimentary concierge service so every part of your trip will be taken care of ensuring you have a hassle free vacation.

We look forward to hearing from you.

Sean Walsh

jamaica Specialist

I'm here to help

    • Type: Villa
    • Sleeps: 8
    • Bedroom(s): 4
    • Bathroom(s): 4
    • Board: Catered
    • Long term rentals: No
    • Pets: No
    • Children: Yes, great for kids
    • Wheelchair: No
    • Eldery or infirm: Not suitable
    • Holiday type: Family, Sea Views, Wedding Villas