Windsong Villa

Property Description
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Guests can also pay per day, for guests ages 16 and older, who stay for one to four days. This can be either prepaid or upon arrival at the Club. For children 12 years of age and younger, our Temporary Memberships are complimentary. Please contact a Villa Specialist for exact pricing! 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.
Bedrooms
This property has 4 bedrooms and sleeps 8 people
Bedroom | Beds | Sleeps | Comments |
---|---|---|---|
Bedroom 1 | Primary | 1 Queen | 2 | |
Bedroom 2 | 2 Single/Twin | 2 | |
Bedroom 3 | 1 King | 2 | |
Bedroom 4 | 1 King | 2 |
Bathrooms
This property has 1 bathrooms
Bathroom | Type | Features | Comments |
---|---|---|---|
Bathroom 4 | full | Toilet, Combo Tub/Shower | En-suite. |
Bathroom 3 | full | Toilet, Combo Tub/Shower | En-suite. |
Bathroom 2 | full | Toilet, Combo Tub/Shower | En-suite. |
Bathroom 1 | Primary | full | Toilet, Tub, Shower | En-suite. Double vanity. |
More Amenities
Category | Amenities |
---|---|
Activities | BeachcombingBird WatchingCyclingDeepSea FishingEco TourismFishingGolfHikingHorseback RidingSailingScuba DivingSnorkelingStand-up Paddle BoardSurfingSwimmingTennisWater SkiingWind SurfingYoga/Pilates |
Attractions | Reefs |
Entertainment | BooksCD PlayerDVD PlayerMovie LibraryMusic LibrarySatellite Or CableSound SystemTelevision |
Events | Weddings ($) |
General | Air ConditioningGolfPoolStaffWifi |
Indoor Features | Bed LinensHair DryerPool/Beach TowelsSafeToiletriesWasher/DryerWet Bar |
Industry Association Recommended Cleaning Practice | SafeHome |
Kitchen | BlenderCoffee MakerCooking UtensilsDining AreaDish WasherFreezerFully Equipped KitchenHighchairIce MakerIron & BoardMicrowaveOvenRefrigeratorStove Top BurnersToaster |
Nearby Facilities | ATM/BankFitness CenterGroceriesHealth & Beauty SpaMassage TherapistMedical ServicesRestaurantsShopping |
Outdoor Features | Dining TableFurnished Terrace/BalconyGardenGarden ChairsGazeboLounging AreaParkingPatioPoolside Lounge ChairsPrivate PoolTerrace |
Staff | Butler(s)ChefGardenerHousekeeper(s)Laundress |
Windsong Villa is equipped with an array of included amenities and services:
• Personal service by the villa staff including a butler, Chef, housekeeper and laundress, gardener, and driver (a full-time complimentary driver is included in full house rentals)
Amenities and services available upon request (extra cost):
• Petrol is an additional cost
• Grocery pre-stock
Property Rates
Rate Category | Period | Rates | Minimum Stay |
---|---|---|---|
Apr 19 - Apr 26, 2025 (4 Bedrooms) |
Apr 19, 2025 to Apr 26, 2025 |
$1,904 per Night $13,325 per Week |
7 night(s) |
Apr 27 - Nov 21, 2025 (2 Bedrooms) |
Apr 27, 2025 to Nov 21, 2025 |
$794 per Night $5,556 per Week |
5 night(s) |
Apr 27 - Nov 21, 2025 (3 Bedrooms) |
Apr 27, 2025 to Nov 21, 2025 |
$1,068 per Night $7,472 per Week |
5 night(s) |
Apr 27 - Nov 21, 2025 (4 Bedrooms) |
Apr 27, 2025 to Nov 21, 2025 |
$1,262 per Night $8,828 per Week |
5 night(s) |
Nov 22 - Nov 29, 2025 (4 Bedrooms) |
Nov 22, 2025 to Nov 29, 2025 |
$1,904 per Night $13,325 per Week |
7 night(s) |
Nov 30 - Dec 14, 2025 (2 Bedrooms) |
Nov 30, 2025 to Dec 14, 2025 |
$794 per Night $5,556 per Week |
5 night(s) |
Nov 30 - Dec 14, 2025 (3 Bedrooms) |
Nov 30, 2025 to Dec 14, 2025 |
$1,068 per Night $7,472 per Week |
5 night(s) |
Nov 30 - Dec 14, 2025 (4 Bedrooms) |
Nov 30, 2025 to Dec 14, 2025 |
$1,262 per Night $8,828 per Week |
5 night(s) |
Dec 15 - Dec 18, 2025 (4 Bedrooms) |
Dec 15, 2025 to Dec 18, 2025 |
$1,904 per Night $13,325 per Week |
7 night(s) |
Dec 19 - Dec 26, 2025 (4 Bedrooms) |
Dec 19, 2025 to Dec 25, 2025 |
$2,223 per Night $15,555 per Week |
7 night(s) |
Dec 26 - Jan 2, 2026 (4 Bedrooms) |
Dec 26, 2025 to Jan 2, 2026 |
$2,223 per Night $15,555 per Week |
7 night(s) |
Jan 3 - Apr 3, 2026 (4 Bedrooms) |
Jan 3, 2026 to Apr 3, 2026 |
$1,903 per Night $13,325 per Week |
7 night(s) |
Apr 4 - Apr 11, 2026 (4 Bedrooms) |
Apr 4, 2026 to Apr 11, 2026 |
$1,903 per Night $13,325 per Week |
7 night(s) |
Apr 12 - Apr 15, 2026 (4 Bedrooms) |
Apr 12, 2026 to Apr 15, 2026 |
$1,903 per Night $13,325 per Week |
7 night(s) |
Apr 16 - Nov 20, 2026 (2 Bedrooms) |
Apr 16, 2026 to Nov 20, 2026 |
$793 per Night $5,556 per Week |
5 night(s) |
Apr 16 - Nov 20, 2026 (3 Bedrooms) |
Apr 16, 2026 to Nov 20, 2026 |
$1,067 per Night $7,472 per Week |
5 night(s) |
Apr 16 - Nov 20, 2026 (4 Bedrooms) |
Apr 16, 2026 to Nov 20, 2026 |
$1,261 per Night $8,828 per Week |
5 night(s) |
Nov 21 - Nov 28, 2026 (4 Bedrooms) |
Nov 21, 2026 to Nov 28, 2026 |
$1,903 per Night $13,325 per Week |
7 night(s) |
Nov 29 - Dec 14, 2026 (2 Bedrooms) |
Nov 29, 2026 to Dec 14, 2026 |
$793 per Night $5,556 per Week |
5 night(s) |
Nov 29 - Dec 14, 2026 (3 Bedrooms) |
Nov 29, 2026 to Dec 14, 2026 |
$1,067 per Night $7,472 per Week |
5 night(s) |
Nov 29 - Dec 14, 2026 (4 Bedrooms) |
Nov 29, 2026 to Dec 14, 2026 |
$1,261 per Night $8,828 per Week |
5 night(s) |
Dec 15 - Dec 18, 2026 (4 Bedrooms) |
Dec 15, 2026 to Dec 18, 2026 |
$1,903 per Night $13,325 per Week |
7 night(s) |
Dec 19 - Dec 26, 2026 (4 Bedrooms) |
Dec 19, 2026 to Dec 26, 2026 |
$2,222 per Night $15,555 per Week |
7 night(s) |
Dec 27 - Jan 2, 2027 (4 Bedrooms) |
Dec 27, 2026 to Jan 2, 2027 |
$2,222 per Night $15,555 per Week |
7 night(s) |
Taxes and Fees
The above rates are subject to the additional fees and taxes below:
Fees:
Damage Waiver: $299.00 flat
Service Fee: $50.00 flat
Additional Rate information:
• Extra guest fee may apply per guest per night. • Rooms are for priced for double occupancy only. Extra guests may be approved by the homeowner. • The rates for this property are dynamic and are constantly changing. The price listed above is only a starting rate and does not necessarily reflect the price for your travel dates. Please contact a reservations agent for exact pricing details. • Staff gratuity - 10% (high season) to 15% (low season) of villa rental rate is to be paid to the head of house in Jamaican or US Dollars at the end of the stay. • Air-conditioning only in bedrooms.
Property Location
Location Type: Beach, Town, Near the Ocean, Oceanview, Waterview
Reviews
Merritt O.
Jan 9, 2018

Windsong Villa
Windsong villa was incredibly beautiful with spectacular views of the Caribbean and the mountains of Jamaica. The staff was outstanding and their kindness and hospitality were what made our family trip extra special. We would love to go back! Our son was recovering from surgery so our activities were limited, but we relished relaxing by our own pool as well as spending time at beautiful Round Hill. We also loved having our own tennis court at Windsong and played every day. The furnishings and grounds at the villa are so wonderful, but it was the stunning views that amazed us every single day - sunrise on one side and sunset on the other. It was an incredible family trip and one we will never forget!