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Wind Song Villa 2 to 4 Bedroom , Montego Bay - Jamaica

Free Van & Driver for the Week!

About Windsong Villa - Montego Bay Jamaica

Windsong is a deluxe private villa with spectacular views day and night! It's located hillside just west of Montego Bay, about 20 minutes from the Montego Bay Airport. The villa has 4 air-conditioned bedrooms with 4 en-suite bathrooms, as well as a private pool, sundecks and poolside bar, as well as a full staff to take great care of you!.

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 ~ the three acres are abundant 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.

*4-Bedroom deluxe private villa on 3 acres with spectacular ocean views east and west.
*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 is in place until October 31, 2024

*  New Tryall Membership Alert:

We are thrilled to announce the exclusive membership affiliation with The Tryall Club, starting November 1st, 2024, and continuing through November 1st, 2025.  As part of this exciting partnership, valued guests will gain access to the luxurious amenities and breathtaking experiences offered by The Tryall Club. Nestled amidst Jamaica's stunning landscape, The Tryall Club promises unparalleled relaxation and adventure for all who visit.

From world-class golf courses to pristine beaches and indulgent spa treatments, there's something for everyone at The Tryall Club. Whether your guests seek a romantic getaway, a family vacation, or an unforgettable retreat with friends, our affiliation ensures that you'll enjoy the ultimate in luxury and hospitality. Members may use most Club facilities at no charge except for 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.

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 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 private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults. TV for DVD's only - no cable service.

Nearby villa is Bambu, and is within walking distance. These two villas total 11 bedrooms.

Click Here for: Things To Do ~ Sites to See
Click Here for: Restaurants in Montego Bay
Click Here for: Golf Courses in Jamaica


We had a great time here at beautiful Windsong 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!

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!

We loved everything – everyone was terrific!


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


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!

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

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!!


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.

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!



  • Queen Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • CD Player
  • Bathtub w/Shower
  • Linens/Towels

COMMON AREA Living/Dining

  • Telephone
  • Internet Access
  • Cable/Satellite TV
  • DVD Player
  • CD Player
  • Radio
  • Patio / Balcony
  • Ceiling Fan
  • Bar
  • Indoor Dining
  • Outdoor Dining


  • Two Twin Beds
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Bathtub w/Shower
  • Linens/Towels


  • Two Twin Beds
  • Ceiling Fan
  • Air Conditioning
  • CD Player
  • Bathtub w/Shower
  • Linens/Towels


  • Two Twin Beds
  • Ceiling Fan
  • Air Conditioning
  • DVD Player
  • CD Player
  • Bathtub w/Shower
  • Linens/Towels

Full Kitchen

  • Refrigerator
  • Cooking Range
  • Oven
  • Microwave Oven
  • Freezer
  • Coffee Maker
  • Blender
  • Toaster

Property Amenities

  • Freshwater Pool (Private)
  • Full Staff
  • Parking
  • Yard
  • Gazebo
  • Outdoor Dining
  • Child Friendly
  • Bar
  • Tennis Court


  • Beach (driving distance)
  • Bicycling
  • Boat Rentals
  • Craft Market
  • Deep Sea Fishing
  • Duty-Free Shopping
  • Golf
  • Gym
  • Spa Facilities
  • Hiking
  • Horseback Riding
  • Kayaks
  • Pool Table
  • Sailing
  • Diving
  • Snorkeling
  • Sunfish Sailboats
  • Tennis
  • Tour Desk
  • Volleyball
  • Water Skiing
  • Wind Surfing
  • Jet Skis

Montego Bay, Jamaica

Rates in USD - Holidays may attract higher rates


April 08, 2024 - April 15, 2024
High Season 4 bedroom $ 1904 

April 16, 2024 - November 22, 2024
Low Season  2 bedroom  $ 715 
Low Season  3 bedroom   $ 961 
Low Season  4 bedroom  $ 1135 

November 23 - 30, 2024
Thanksgiving Holiday  $ 1904 

December 01, 2024 - December 14, 2024
Low Season  2 bedroom   $ 715 
Low Season  3 bedroom   $ 961 
Low Season  4 bedroom  $ 1135 

December 15, 2024 - December 18, 2024
High Season  4 bedroom  $ 1904 

December 19, 2024 - December 26, 2024
Christmas - Dec 19-26 or 20-27

or any 7 nights that includes Dec 25th.

Additionally any 7 nights (eg. Dec 17-24) over Christmas $ 2223 

December 27, 2024 - January 02, 2025
New Year's - Dec 26-Jan 2 or Dec 27-Jan 3

or any 7 nights that includes Dec 31st  $ 2223 

January 03, 2025 - April 18, 2025
High Season    4 bedroom     $ 1904 

April 19, 2025 - April 26, 2025
Easter - Any 7 nights that includes Easter $ 1904 

April 27, 2025 - November 21, 2025
Low Season    2 bedroom  $ 794 
Low Season    3 bedroom    $ 1068 
Low Season    4 bedroom     $ 1262 

November 22 - 29, 2025
Thanksgiving Holiday   $ 1904 

November 30, 2025 - December 14, 2025
Low Season  2 bedroom  $ 794 
Low Season  3 bedroom  $ 1068 
Low Season  4 bedroom  $ 1262 

December 15, 2025 - December 18, 2025
High Season   $ 1904 

December 19, 2025 - December 26, 2025
Christmas - Dec 19-26 or 20-27

or any 7 nights that includes Dec 25th.

Any 7 nights (eg. Dec 17-24)  prevents Christmas $ 2223 

December 26, 2025 - January 02, 2026
New Year's - Dec 26-Jan 2 or Dec 27-Jan 3

or any 7 nights that includes Dec 31st $ 2223 

Windsong bookings includes a full time driver as long as 4 bdrms are rented.

The Gas & the Driver gratuity is not included / driver gratiuty would be $175. for the week

All transportation within one hour of the villa

Round trip airport transfers from the Montego Bay Airport

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