Caribbean / Jamaica / Montego Bay

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.

up to 4
up to 8
from 5
Min. Nights


  • 4-Bedroom deluxe private villa on 3 acres ~ spectacular ocean views east and west
  • Open-air villa
  • 20’ x 40’ Private tiled pool and poolside bar
  • A full-time complimentary driver is included in full house rentals (4 bedrooms).  Guests are responsible for all petrol. 
  • Full staff: butler, chef, housekeeper, gardeners, laundress
  • Brand new  55“ UHD Samsung  6 Series TV ~ library of movie DVDs and music CDs
  • Wi-Fi
  • All bedrooms have air-conditioning, fans, safes, robes, and bathroom amenities
  • Complimentary crib & highchair
  • Glorious trade winds, breathtaking sunrises, and sunsets
  • Round Hill Membership
  • Introducing the NEW Tryall Membership beginning November 01, 2024.

Windsong is a luxurious 4-bedroom private villa retreat nestled in the low foothills overlooking Montego Bay’s western coastline. 

Windsong Villa is a beautifully designed and very private home conveniently located just minutes from Montego Bay’s renowned Round Hill property where guests enjoy complimentary beach membership. 

This charming tropical villa encapsulates a complete Jamaican experience. Noted for its sweeping panoramic views, airy rooms, lush rolling landscape, and well-laid-out tropical gardens, Windsong Villa is itself simply gorgeous and exquisitely inviting – from the outside in. 

The home and its elegant features cleverly blend the beauty of nature into the indoor settings and guests get an instant sense of serenity upon arrival. 

The Windsong experience begins as soon as you turn onto the circular driveway encompassing the shade of our majestic banyan tree - resplendent with hanging orchids - and continues as you enter the welcoming courtyard with its vibrant tropical plants and water fountains inviting you to enjoy the finest of Caribbean living. 

Windsong’s unique hill located on the outskirts of Montego Bay is perfect to marvel at the most amazing views whilst enjoying the favorable trade winds of the season. The east view captures the rising sun over Montego Bay, while to the west is an equally lovely vista of Round Hill and breathtaking tropical sunsets above the lush green hills of Hanover. 

With soothing water features throughout, you will feel instantly welcome and at home. The well-cared grounds are thoughtfully filled with a variety of local tropical trees, plants and flowers, and fruit trees – the produce of which make it to the breakfast table when in season. Wander at leisure through this extensive garden and get to know Jamaica’s flora. 

The villa is managed by a highly experienced team of staff who will ensure that your stay here meets and exceeds your expectations. The team will be happy to offer suggestions and recommendations when asked. 

Plan your meals with the skillful creative chef who will work with your tastes and dietary needs – serving up meal after sumptuous meal made from the freshest of ingredients, for your culinary delight. 

You may wish dinner to be served by candlelight indoors or in the more casual al fresco dining area on the verandah overlooking the pool. The poolside bar is kept stocked with ice and drinks for your convenience, and the sound system supplies music both indoors and out. 


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

Main Level

Master Bedroom
Queen-size 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
King size 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
King size or twin beds at guests’ option; en-suite bathroom with tub-shower Combination. Radio/cassette/CD player. French doors to a private terrace and ocean view.

Bedroom 4
King size 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.

Round Hill 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, afternoon tea, Wednesday Manager's Cocktail Party, basketball court, tennis courts, and unforgettable long sunsets from the waterfront terrace. Guests must check in at the front desk on their first visit before enjoying the amenities at Round Hill.  Round Hill will close from September 3 to October 10, 2024, for seasonal maintenance and reopen on October 11, 2024.

Additional Amenities (fee required):

  • Kids’ Club: The cost for Pineapple Kid’s Club is US$27.50 daily per child. Children three years to twelve years old.  Children zero to three years old have the same cost but must be accompanied by a nanny. The hours of the Club are 9 am-5 pm. Lunch is not included (parents collect children for lunch).
  • Gym: $50 per person per day for any guests in Round Hill Villas or villas with Round Hill membership (this fee should be paid at the front desk before using the gym)
  • Spa
  • Salon
  • Range of water sports
  • Beach Parties

Please note: Round Hill membership is guaranteed for guests traveling until November 1, 2024. ** The Round Hill Board of Directors has announced that Resort membership for this villa will not be renewed after Nov 1st, 2024. Round Hill reserves the right to change or alter its membership packages with no advance notice.  Prices are liable to change without notice. There may be occasions when some or all the facilities of the hotel may be closed for membership guest services due to a private hotel event.


Starting from November 1st, 2024, Windsong Villa proudly announces its complimentary membership with The Tryall Club, extending until November 1st, 2025. This exciting addition 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.

Members may use most Club facilities at no charge with the exception of the tennis shop, ball boys, bar & restaurant, spa, grocery, motorized water sports, nanny services, and golf.  Complimentary amenities include the beach, non-motorized water sports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party, and various special events.

Please note: Tryall Club membership is guaranteed for guests traveling through November 1, 2025.  There may be occasions when some or all the facilities of the hotel may be closed for membership guest services due to a private hotel event. The Tryall Club reserves the right to change or alter its membership packages with no advance notice.


4 Bedrooms, 4 Bathrooms

Sleeps 8 Guests

  • Bedrooms Only
  • Kids Club Membership
  • Golf Nearby
  • Wi-Fi
  • Poolside Bar
  • Full-time Complimentary Driver
  • Butler
  • Housekeeper
  • Gardeners
  • Laundress
  • Chef
  • Hair Dryers
  • Bathrobes
  • 3 Acres
  • High-speed Internet Access
  • Available for Weddings
  • Round Hill Membership (Outside the Gate)
  • iPod Dock(s)
  • Sirius XM Radio


Pool Details

pool is 40' x 20'

Distance Details

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

Rates and Availability

Accidental Damage Waiver
A $149 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
High Season: 7-night minimum stay required
Low Season: 5-night minimum stay required
Festive Season: 7-night minimum stay required
Check-In Times
Check in: 3:00 PM - Check out: 11:00 AM
Rate Policies
Extra Person Charge: $40.00 per night
Wedding Details

Wedding Venue Surcharge: $30 per person | Maximum Guests: 50 

Villas in Proximity: Almond Hill, Bambu, and Summertime at Silver Sands

Surcharge for festive bookings
5% surcharge for festive bookings



Staff & Service: Excellent - Amazing staff
Accommodations: Excellent- Amazing house
Overall Expectation: Exceeded
Will you return: Yes (Soon!)

-Moran Party

Staff & Service: Excellent - The staff was exceptional. They met every request we had. They anticipated our needs and made us feel welcome
Accommodations: Excellent - The villa is beautifully decorated and well-maintained. We especially appreciated the Jamaican artwork. The furniture was very comfortable and adequate for a full house of people.
Will you return?: Yes
Overall Expectation: Exceeded

-Ward Party

Staff & Service: Excellent - Felt so cared for all week. Amazing staff - DJ, Aldine, Everton, Voilene, and Sharon were the absolute best! Food was delicious!
Accommodations: Excellent
Overall Expectation: Exceeded
Will you return: Yes

-Brennan Party

Welcome by staff on arrival: Excellent
Chef: Excellent
Butler: Excellent
Housekeepers: Excellent
Groundsmen: Excellent
Handling of groceries, monies: Excellent

Furnishings & fixtures: Excellent
Bedrooms: Excellent
Water Pressure: Excellent
Air Conditioning: Excellent
Lighting/Electricity: Excellent
Cleanliness: Excellent
Television: Excellent
Telephone: Excellent
Pool & Pool Area: Excellent
Wi-Fi: Excellent
Grounds: Excellent
Overall Comfort: Excellent

ADDITIONAL COMMENTS: Excellent staff! Very accommodating, and very patient with the children. Over all, we could not have been treated any better.

-Fitzsimions Party

Staff was great! Food was superb. Location was exceptional. A wonderfully relaxing time!!

Marc A.

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.

We had a great time here in Jamaica at your beautiful Villa and Round Hill...loved DJ & Rushane, wonderful and always pleasant & helpful. We love the grounds, we played Tennis & jetskied. We will remember our stay. Our family enjoyed our vacation. At the pool, the landscape, tea time at 4, so blessed and we want to come back to Windsong. We did enjoy laying by the pool, perfect! We will be back!

Christine G.

We loved everything – everyone was terrific!

Ellen L.

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

Chris B.

Wonderful!! We will be back.

Gary D.

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

Henry M.

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.

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

Graham H.

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.

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.

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.

It's Day Four and we all love Windsong. It's a lovely villa, beautifully decorated, and well maintained, and the views are magnificent. And the staff members are great!
Feel The Rhythm
Feel The Rhyme
Raise Your Glass
It's "Windsong" Time

-Ward Party

Staff & Service: Excellent - Very pleasant! Made the stay perfect!
Accommodations: Excellent
Overall Expectation: Exceeded

-Fleming Party
Will Return: Yes

Staff & Service: Excellent - Staff is exceptional!
Accommodations: Excellent
Overall Expectation: Exceeded
Additional Comments: Beautiful villa! We will return!

-Ballard Party
Will Return: Yes

Staff & Service: Excellent - Thank you for the amazing hospitality.
Accommodations: Excellent
Overall Expectation: Exceeded

-Arisom Party
Will Return: Yes

Staff & Service: Excellent
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-D'Amato Party

Staff & Service: Excellent
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-Berry Party

Staff & Service: Excellent
Accommodations: Excellent
Overall Expectation: Exceeded
Additional Comments: DJ, Chef, Everson, and Vatteria are simply the best!

-Mitchell Party
Will Return: Yes

Staff & Service: Excellent - The food presentation and service by all staff members were surperb.
Accommodations: Excellent - Exceptional
Overall Expectation: Exceeded
Will Return: Yes

-Antoine Party

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 favorite part was the view. It was nice to watch the sunrise 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 made my trip special and I hope it does the same for many others.

-Darby Party

Staff & Service: Excellent
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes
Additional Comments: The staff was wonderful and made us all feel at home! Chef Aldine made the most delicious meals and accommodated all of our requests. The home was gorgeous! Everything from the views to the decor was perfection!!

-Ross/Kelsey Party

Staff & Service: Excellent - Excellent, thank you all!!
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes
Additional Comments: We had a wonderful time! Can't wait to come back. The staff was excellent - We loved it!!

-Hample/Mac Millan Party

Staff & Service: Excellent - Everyone was wonderful and exceeded our expectations in everything
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-Zimmerman Party

Staff & Service: Excellent
Accommodations: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-Fitsimmons Party

The staff and service were excellent as well as the accommodations. Exceeded overall expectations. I would return and recommend to others.


Friendly, kind, and easy-going. Exactly the type of service we like! Thank you. Overall the house is very comfortable and relaxing. We loved it. Windsong is exceptional.


This has been an incredible experience. DJ and Ardene are amazing. I will be back and will recommend to family and friends. Love and blessings!

Perry Party

The entire staff was outstanding! Very welcoming and attentive. The food was amazing! The service overall was first class!! Windsong is a beautiful villa! The website does not do this place justice.

As stated above, this villa and the overall experience was exceptional! My family and I had an amazing vacation and we thank Linda Smith's staff and family for creating such a dream vacation.

Johnson Family

Villa information may change without notice and should be confirmed with our villa rental specialists.

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