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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

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 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.

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 beach access, pool with chaise lounge chairs, jogging trail, gift shop, logo shop, beach bar, piano bar, Wednesday Manager's Cocktail Party,

Continental cuisine in the hotel restaurant ... and unforgettable long sunsets from the waterfront terrace.

Additional charges will apply for the Round Hill Spa, tennis courts, Pineapple Kids Club, fitness center, a range of water sports and parties (Monday beach party and Friday Jamaica Night). Membership valid until October 31 each year.

Round Hill closes once a year in the fall. This year they will close Sept 6 - Oct 6, 2023 

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

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



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.


  • 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

WEEKLY RATES in US dollars


High Season  Jan 3 - April 15, 2024 

1-4 Bedrooms $13,326 


Low Season April 16 - December 14, 2024

2 Bedroom $5,005

3 Bedroom $6,727

4 Bedroom $7,945.


* Thanksgiving NOV 23 - 30, 2024 

1-4 Bedrooms $13,328


Christmas & New Year December 19, 2024 - January 2, 2025

1-4 Bedroom $15,561. 

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

  • Book Now / Request Dates