Windsong

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
Bedrooms
up to 8
Guests
4
Bathrooms
from 5
Min. Nights

Overview

  • 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
  • High-speed DSL Internet access
  • All bedrooms have air-conditioning, fans, safes, robes, and bathroom amenities
  • Complimentary crib & highchair
  • Glorious trade winds, breathtaking sunrises, and sunsets
  • Round Hill Membership

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. 

Accommodations

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

Round Hill Membership 

complimentary beach, two connecting heated pools for parents & children, jogging trail. For various fees: Pineapple Kids Club, tennis, hair salon & spa, bars & restaurants, gift shops, water sports, Internet room, afternoon tea, beach parties Mon-Wed-Fri. Current Round Hill membership runs through October 31, 2022.  Please note: The resort will be closed from September 6 to October 6, 2022. 

Please note: There may be occasions when some or all the facilities for the hotel may be closed for membership guest services due to a private hotel event. Round Hill reserves the right to change or alter its membership packages with no advance notice.



Amenities

4 Bedrooms, 4 Bathrooms

Sleeps 8 Guests

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

Details

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

Travel Dates Bedrooms Min. Night Stay Nightly Rates
November 27, 2022 - December 14, 2022
Low Season
2 5 $ 643 *
November 27, 2022 - December 14, 2022
Low Season
3 5 $ 865 *
November 27, 2022 - December 14, 2022
Low Season
4 5 $ 1,022 *
December 15, 2022 - December 18, 2022
High Season
4 7 $ 1,713 *
December 19, 2022 - December 26, 2022
Christmas Holiday
4 7 $ 2,000 *
December 27, 2022 - January 02, 2023
New Year's Holiday
4 7 $ 2,000 *
January 03, 2023 - April 07, 2023
High Season
4 7 $ 1,713 *
April 08, 2023 - April 15, 2023
Easter Holiday
4 7 $ 1,713 *
April 16, 2023 - November 17, 2023
Low Season
2 5 $ 643 *
April 16, 2023 - November 17, 2023
Low Season
3 5 $ 865 *
April 16, 2023 - November 17, 2023
Low Season
4 5 $ 1,022 *
November 18, 2023 - November 25, 2023
Thanksgiving Holiday
4 7 $ 1,328 *
November 26, 2023 - December 14, 2023
Low Season
2 5 $ 643 *
November 26, 2023 - December 14, 2023
Low Season
3 5 $ 865 *
November 26, 2023 - December 14, 2023
Low Season
4 5 $ 1,022 *
December 15, 2023 - December 18, 2023
High Season
4 7 $ 1,713 *
December 19, 2023 - December 26, 2023
Christmas Holiday
4 7 $ 2,000 *
December 27, 2023 - January 02, 2024
New Year's Holiday
4 7 $ 2,000 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Wedding Details

Max 50 guests. *$15 surcharge applies

Rate Policies

A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas and New Year’s Eve.

Check In Times

Check in: 3:00 PM - Check out: 11:00 AM

Security Deposit Details

US $99 Damage Deposit Waiver Fee: A US $99 Damage Deposit Waiver Fee applies to your reservation. It is our goal to ensure that you have a remarkable experience at our villas. And we understand that accidents happen. In lieu of a large security deposit, your reservation will include a $99 Accidental Damage Waiver fee. This will cover accidental damages of up to $2,000 that occur during your stay.

5% surcharge for festive bookings

Exclusive Offers

Your next villa vacation just got even better. Reserve your dream 2023 villa vacation by December 4th, 2022, and you'll receive up to a $2,000 Concierge Credit to use towards luxury in-villa services and unforgettable experiences. From private chef service to a sunset catamaran cruise, what will you add to your villa experience?


Offer valid for new bookings made between 11/20/22 – 12/04/22 travel from 1/9/23 - 12/31/23. Amount is based on the base villa cost only. Minimum booking value of $5,000 applies. Valid for select pre-paid services only. Services offered are subject to availability. The value of any unused credit is non-refundable. Credit cannot be applied towards booking value. May not be combinable with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply; please call for full details.

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Location

Reviews

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

Marc A.

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.

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 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 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.

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.

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

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

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.

Dunleavy

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

McKinnon

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

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