Jamaica Villas by Linda Smith

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Windsong • Montego Bay, Jamaica Villa

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About Windsong

Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista of Round Hill, the sea and the sunset.

  • 4-bedroom deluxe private villa on 3 acres ~ spectacular ocean views east and west
  • 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 fax machine
  • glorious tradewinds, breathtaking sunrises and sunsets
  • Round Hill membership: complimentary beach, two connecting heated pools for parents & children, jogging trail. For various additional fees: Pineapple Kids Club, gym, tennis, hair salon & spa, afternoon tea, 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 every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night.

Windsong is an exquisite and very private home four minutes from Round Hill. Designed by noted architect Kasimir Korybut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ~ the west, an equally lovely vista of Round Hill, the sunset and ocean. 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 bougainvillea. Five fountains grace the indoor gardens. From the central fountain, stone walkways lead to the Great Room, inside dining room, bedrooms and bar ... and the wonderful 700-square-foot verandah with its casual al fresco 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. TV with cable service, along with a sound system that carries music to indoor and outdoor living areas. The poolside bar is always stocked with ice and drinks.

For larger groups, Windsong can be rented with its neighboring villas, Bambu and Goat Hill ~ each within walking distance ~ for a compound of 13 bedrooms, 3 swimming pools, 2 tennis courts and 16 staff including 3 cooks. This is a convenient and excellent combination for wedding parties and family reunions.


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, 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. Television for watching DVDs and videos - no cable service in bedroom. French doors to private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults.

Round Hill Hotel and Beach Club Membership

A special amenity available to guests in this villa is membership at Round Hill ... just minutes from the villa and one of the finest private resorts on Jamaica's North Coast.

Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar ... and unforgettable long sunsets from the waterfront terrace.

For additional charges, members may enjoy the spa, tennis courts, afternoon tea, Pineapple Kids Club, fitness center, salon, a range of water sports and beach parties.

Internet access is $22 per day for up to 3 devices. This may be paid at reception. The internet service can be upgraded to Premium (faster speed) for $33 per day for up to 3 devices.

Round Hill was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world."


  • Round Hill will be closed September 5 - October 12, 2017 for their annual maintenance.
  • Round Hill membership is guaranteed for guests travelling through October 31, 2017. Some villas not guaranteed if travel dates are beyond October 31, 2017. Ask our Villa Specialists if you have any questions.

The Tryall Club Membership

A significant amenity for guests in this villa is membership at the excellent Tryall Club.  On 2,200 acres, Tryall’s golf course is among the most beautiful in the world.  Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events.  The resident pro offers workshops and private lessons.   The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call.  All white attire required.

The beach is well planned for parents and children. Have lunch at the beach bar.  Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it).  Jog the marked trails. Snorkeling, kayaking, Hobie Cat and sunfish are complimentary.  Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees.  Enjoy weekly events like  complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

On the hill, enjoy the historic Great House for daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar.  Also at the Great House is the new Usain Bolt Games Room open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs and HDTV. And don’t miss the massive Tryall pool. The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads and everyone from teens to octogenarians.

For a great write-up of the Tryall Club, see Dana Vachon's article Club Jamaica in Departures Magazine.

The Tryall Club was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world.”

Tryall Club Golf Course NoteThe front 9 holes of the golf course will be closed from May 13 - October 16, 2017 for extensive renovation. The recently renovated back 9 holes of the golf course will remain open all summer. Members & guests who wish to play 18 holes between May 13th and Oct 16th can play the back 9 holes twice. Multiple tee box options will be available in order to give a different feel to the golf course. The driving range will remain open as normal. All green fees during this period will be charged at our 9 hole rates regardless of whether the golfer plays 9 or 18 holes. Normal cart and caddy fees will apply.

NOTE: Tryall Club membership is guaranteed for guests travelling through November 30, 2017. Not guaranteed if travel dates are beyond November 30, 2017. Ask our Villa Specialists if you have any questions.

Rental Rates

Season Bedrooms Weekly Rate
High Season 2018
December 15 - April 14
1–4 $9,900
Low Season 2017
April 15 - December 14
1–2 $3,500
Low Season 2017
April 15 - December 14
3–4 $7,000
March 31 - April 7
Easter week is any 7 nights that includes Easter Sunday
1–4 $9,900
November 18 - November 25
1–4 $8,450
December 19 - December 26
1–4 $11,900
New Year's
December 26 - January 2
1–4 $12,900
Link to Calendar

Booking Calendar

Guest Reviews

  • Staff was great! Food was superb. Location was exceptional.

    Marc A – March 2016

  • This place is insaaane! So stunning and well designed... the photos don't do it justice! Staff were wonderful and warm; made us feel very welcome!

    Christine P – March 2016

  • We loved everything – everyone was terrific!

    Ellen L – December 2015

  • The staff were very helpful and kind. Very pretty villa – the landscape is beautiful & views were amazing!

    Chris B – November 2015

  • Wonderful!! We will be back.

    Gary D – October 2015

  • Chef did an excellent job, everything was delicious. DJ provided superior service, Valerie kept everything spotless. Lovely!

    Henry M – September 2015

  • The staff were wonderful, they went beyond to make our stay so enjoyable. We shall always remember Windsong, we took a 1000 photos. You were all superb – Thank you!

    Rita D – August 2015

  • The staff made our experience even better than we ever thought. The villa was exceptional. We will return!

    Graham H – April 2015

  • 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 Round Hill 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 accommodating - 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 accessible 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.

    Ashley Y – March 2015

  • Dear Linda,

    The staff are outstanding and so good at what they do. They are all so lovely. Our stay at Windsong could not have been any more fun and relaxing!

    Reg S. - Washington, DC - March 2011

  • Dear Linda,

    The staff are all exceptionally kind and do any amazing job taking care all our needs and the house and grounds are so beautiful and comfortable!

    Beth S. - Baltimore, MD - March 2011

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Villas by Linda Smith 100 Fordham Road, Bldg. C Wilmington, MA, 01887 Tel 301.229.4300 Email linda@jamaicavillas.com
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