Villas Caribbean Jamaica Montego Bay
Windsong is an exquisite and very private home. 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 towards Negril, the sea, and the sunset.
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Overview
- 4 bedrooms
- 4 bathrooms
- Sleeps 8
- 5 staff
- Bedrooms Only
- Golf Nearby
- Kids Club Membership
- Poolside Bar
- Wi-Fi
- $794+/night
Windsong is a luxurious 4-bedroom private villa retreat nestled in the low foothills overlooking Montego Bay’s western coastline.
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.
- 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
- Introducing the NEW Tryall Membership beginning November 01, 2024.
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. French doors to a private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults.Tryall Membership
All guests of Windsong must pay a resort entry fee of US$34 per person per day plus a 15% tax to have access to the resort amenities at the Tryall Club. Children 13-15 years of age pay a discounted rate of 50% off plus 15% tax and children 12 & under are complimentary.
After paying the Temporary Membership Fee, 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 30, 2024. 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.
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Villa Details
Amenities
- 3 Acres
- Available for Weddings
- Bathrobes
- Bedrooms Only
- Butler
- Chef
- Full-time Complimentary Driver
- Gardeners
- Golf Nearby
- Hair Dryers
- High-speed Internet Access
- Housekeeper
- iPod Dock(s)
- Kids Club Membership
- Laundress
- Poolside Bar
- Sirius XM Radio
- Wi-Fi
Distances to nearby attractions
- Beach: 11 minutes to the Tryall Club
- Town: 20 minutes via driver
- Airport: 20 minutes via driver
Pool details
- pool is 40' x 20'
Weddings
- Wedding Venue Surcharge: $30 per person | Maximum Guests: 50
- Villas in Proximity: Almond Hill, Bambu, and Summertime at Silver Sands
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Pricing
Travel dates Bedrooms Min. stay Nightly rate Weekly rate Available? December 15, 2024 – December 18, 2024 • High Season 4 bedrooms 7 nights minimum stay $ 1,904 USD nightly $ 13,325 USD weekly Booked Fully booked (no dates available) 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) that prevents a Christmas reservation will be invoiced at the Christmas rate. 4 bedrooms 7 nights minimum stay $ 2,223 USD nightly $ 15,555 USD weekly Booked Fully booked (no dates available) December 27, 2024 – January 2, 2025 • New Year's - Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that includes Dec 31st. 4 bedrooms 7 nights minimum stay $ 2,223 USD nightly $ 15,555 USD weekly Booked Fully booked (no dates available) January 3, 2025 – April 18, 2025 • High Season 4 bedrooms 7 nights minimum stay $ 1,904 USD nightly $ 13,325 USD weekly Booked Fully booked (no dates available) April 19, 2025 – April 26, 2025 • Easter - Any 7 nights that includes Easter Sunday 4 bedrooms 7 nights minimum stay $ 1,904 USD nightly $ 13,325 USD weekly Booked Fully booked (no dates available) April 27, 2025 – November 21, 2025 • Low Season 2 bedrooms 5 nights minimum stay $ 794 USD nightly $ 5,556 USD weekly Booked Fully booked (no dates available) April 27, 2025 – November 21, 2025 • Low Season 3 bedrooms 5 nights minimum stay $ 1,068 USD nightly $ 7,472 USD weekly Booked Fully booked (no dates available) April 27, 2025 – November 21, 2025 • Low Season 4 bedrooms 5 nights minimum stay $ 1,262 USD nightly $ 8,828 USD weekly Booked Fully booked (no dates available) November 22, 2025 – November 29, 2025 • Thanksgiving Holiday 4 bedrooms 7 nights minimum stay $ 1,904 USD nightly $ 13,325 USD weekly Booked Fully booked (no dates available) November 30, 2025 – December 14, 2025 • Low Season 2 bedrooms 5 nights minimum stay $ 794 USD nightly $ 5,556 USD weekly Booked Fully booked (no dates available) November 30, 2025 – December 14, 2025 • Low Season 3 bedrooms 5 nights minimum stay $ 1,068 USD nightly $ 7,472 USD weekly Booked Fully booked (no dates available) November 30, 2025 – December 14, 2025 • Low Season 4 bedrooms 5 nights minimum stay $ 1,262 USD nightly $ 8,828 USD weekly Booked Fully booked (no dates available) December 15, 2025 – December 18, 2025 • High Season 4 bedrooms 7 nights minimum stay $ 1,904 USD nightly $ 13,325 USD weekly Booked Fully booked (no dates available) December 19, 2025 – December 26, 2025 • Christmas - Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally any 7 nights (eg. Dec 17-24) that prevents a Christmas reservation will be invoiced at the Christmas rate. 4 bedrooms 7 nights minimum stay $ 2,223 USD nightly $ 15,555 USD weekly Booked Fully booked (no dates available) December 26, 2025 – January 2, 2026 • New Year's - Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that includes Dec 31st. 4 bedrooms 7 nights minimum stay $ 2,223 USD nightly $ 15,555 USD weekly Booked Fully booked (no dates available) Please note
- Rate policies: Extra Person Charge: $40.00 per night
- Rate notes: High Season: 7-night minimum stay required Low Season: 5-night minimum stay required Holiday Season: 7-night minimum stay required (Easter Sunday, Thanksgiving, Christmas, and New Year’s Eve.) *Rates are subject to change without notice. Please check with your villa specialist to confirm.
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Availability
2024
March 2024
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January 2032
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Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.
7 bedroom 7.5 bath Jamaica villa in Montego Bay
The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a time warp, to visit Jamaica's countryside is to experience another Jamaica of 30 years ago. The pace is slow, the lifestyle uncomplicated, the people are kind and calm, the service is relaxed and meals are served family style. For larger groups there are 2 extra bedrooms, just 50 paces away that may be available for an occupancy of 18 pax.
4 bedroom 4 bath Jamaica villa in Montego Bay
Almond Hill was designed by Prince Kasimir Korybut in 1993. It was brilliantly renovated, creating a contemporary beautifully decorated home with french doors opening from all of the bedrooms to the garden and bathrooms. Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a five-minute drive from Round Hill where guests enjoy complimentary resort membership.
4 bedroom 4 bath Jamaica villa in Montego Bay
Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.
4 bedroom 4 bath Jamaica villa in Montego Bay
Seaside was completely renovated & refurbished in 2018. This amazing sea front property is one of the newest premier villas at Round Hill.
4 bedroom 4 bath Jamaica villa in Montego Bay
Summertime at Silver Sands has a wonderful beach vibe, it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all overlooking the Caribbean sea.