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Tradewinds at the Tryall Club
What we like most
- Completely renovated in January 2018, offering modern and stylish interiors.
- Heated infinity pool, hot tub, and outdoor amenities for a luxurious beachfront experience.
- Enjoy the services of a chef, butler, housekeeper, laundress, and gardener.
Insider's Knowledge
- Membership (at extra cost) to Tryall Club with access to beach, tennis, gym, water sports, and more.
- Sonos sound system, media room, well-equipped bar area, and large curved TVs for a complete experience.
- 300 feet of Caribbean Sea frontage with outdoor shower, ocean-edge dining, and water sports.
Places close by
- Tryall Club Amenities: 3 minute walk or 1 minute golf cart ride to beach club, pro shop, driving range, and casual beach bar.
- Montego Bay: Accessible for further exploration, 28 minutes drive.
- Chukka Ocean Out-Post Activities: 7 minutes drive
Elegant seaside living
Tradewinds has one of the best locations in Tryall Club and I was treated to an entire evening here. We were completely spoiled by the incredible staff and we dined, listening to the sounds of the birds and the sea, in total comfort and luxury. I especially loved the separate bedroom/cottage by the pool, opening not one set, but three sets of French doors to the amazing views of surrounding nature would be my dream start to any day!
Description
Welcome to Tradewinds at the Tryall Club, a luxury 4 bedroom private villa located in the famous Tryall Club in Montego Bay.
One of just a handful of Tryall villas with its own private beach (depending upon the tide), Tradewinds On The Sea has the most spectacular sea views.
With its charming detached bedroom cottage, great gathering spaces such as the ocean side pool deck and quarter acre lawn, Tradewinds is a perfect family home away from home.
The villa is set right on the shoreline and is built in the classic Caribbean style with 21st century enhancements. Built on one level with a separate detached cottage, Tradewinds affords an enviable ocean frontage with an extensive lawn to the east. Light, airy, and a lovely free-flowing sense of space, Tradewinds offers exceptionally comfortable accommodation with an immediately appealing oceanfront style.
The open-plan sitting room and dining room flow into the adjacent media room with all areas having the ocean's most stunning panorama. Soft watery colors such as eau de Nil and pale blue reflect the sea and sky tones. The beautiful new swimming pool with integrated hot tub directly overlooks the sea and the surrounding terrace catches the sun all day long. To the right of the sitting room is a very spacious veranda with relaxing furniture and flat-screen television.
The bedrooms all enjoy sea views and have immaculate en suite bathrooms with walk-in showers. Three bathrooms also have outdoor showers, and one has a tub. The primary bedroom has a separate small sitting room with the most idyllic sheltered view over the bay.
STAFF
When you at the luxurious Tradewinds at the Tryall Club you will be taken care of by our wonderful team of staff. Our butler, chef, housekeeper, laundress and gardener will ensure you have relaxing experience… you won’t want to leave!
AMENITIES
• AC bedrooms
• Heated walk-in infinity swimming pool
• 8 person spa with waterfall
• Outdoor fire pit
• 2 golf carts
• 3 bedrooms with king beds
• 1 bedroom with twin beds
• Free Wifi
• Cable television
• SONOS
• Children Welcome
• Indoor/Outdoor Dining
• Safe
• Games available
• Flat screen SMART Televisions throughout
SEE "ADDITIONAL INFORMATION" BOX BELOW FOR INFO ON TRYALL CLUB MEMBERSHIP FEES. CONTACT US FOR FURTHER INFORMATION.
Area description
Read more about the Tryall Resort
Location
| Nearest airport |
Montego Bay Airport |
17 km |
|---|---|---|
| Nearest beach | Tryall Private Beach | 100 meters |
Amenities
-
Bedroom(s): 4 ( Sleeps 8 )
1 Double with en-suite, 3 Twin with en-suite -
Bathroom(s): 4
2 Baths, 4 Showers, 4 Wash basins, 4 Toilets - General facilities: Balcony / Deck, Ceiling Fans, Garden, Garden View, High Speed Internet, Panoramic Views, Private Location, Private Terrace, Security, Terrace, Wifi
- Indoor facilities: Air conditioning, All Bedrooms Air Conditioned, All Bedrooms En Suite, CD Player, Coffee Maker, DVD Player, iPOD Docking Station, Luxury Finishes, Phone, TV
- Outdoor facilities: Beach Access, Enclosed Garden, Outdoor Shower, Patio, Private Plunge Pool, Private Terrace, Restaurants nearby, Sea Views, Sun Loungers, Sun Umbrellas, Swimming pool
- Services: Breakfast included, Chef Included, Cleaning inclusive, Concierge Service, Kids club, Linen provided, Maid service, Towels provided
Availability
Rates
- Concierge Service
- Expert Advice
- Personally Inspected Villas
| - | Nightly rate | Min. Stay | |||
|---|---|---|---|---|---|
| Rate summary | $ 2,286 - $ 5,000 | $ 16,000 - $ 35,000 | 5 Nights | - | |
| Low Season 2025 26-Apr-2025 - 25-Jul-2025 | $ 2,414 | 5 Nights | |||
| Low Season 2025 26-Jul-2025 - 31-Oct-2025 | $ 2,286 | 5 Nights | |||
| Low Season 2025 01-Nov-2025 - 21-Nov-2025 | $ 2,414 | 5 Nights | |||
| Thanksgiving 2025 22-Nov-2025 - 28-Nov-2025 | $ 3,286 | 7 Nights | |||
| Low Season 2025 29-Nov-2025 - 12-Dec-2025 | $ 2,414 | 5 Nights | |||
| High Season 2025 13-Dec-2025 - 19-Dec-2025 | $ 3,286 | 5 Nights | |||
| Festive Season 2025 20-Dec-2025 - 02-Jan-2026 | $ 5,000 | 14 Nights | |||
Additional Information
RATES BASED ON FULL OCCUPANCY. SOME SEASONS WILL ALLOW LOWER RATES FOR FEWER OCCUPANTS. PLEASE INQUIRE.
- Tax: 10%
- Non-refundable TC admin Fee: 7.5%
**Thanksgiving may be charged at Premium rate.**
Security deposit $1000
Recommended staff gratuity at the end of your stay is 15% of the villa rental in low season and 10% in high season. Plan to pay your grocery and gratuity monies in cash: US dollars or Jamaican dollars.
THE TRYALL CLUB MEMBERSHIP The Tryall Club is a private members club, so it requires all guests to become members during their stay via a Temporary Membership Fee, which will be charged upon arrival at check-in.For guests arriving from 1st January 2025, temporary membership dues are as follows: Guests 16 years and older pay US $34 per day for stays of 1 to 4 days and US $170 for stays of 5 to 7 days thereafter. Children 13 to 15 years old will pay US $17 per day and $85 for 5 to 7 days thereafter. For children 12 years and under, the Temporary Membership Dues are complimentary. All dues incur a 15% service charge and are subject to change.
The membership includes use of the beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party. For additional fees, you can get golf and tennis lessons, Happy Hour, hair salon & spa treatments, bars & restaurants, boutique shopping, motorized water sports, Reggae Nights, and Beach Parties on selected nights.
Jacuzzi Disclaimer:
***Please note that while we strive to maintain all amenities in perfect working condition, Jacuzzis and hot tubs cannot be guaranteed. These units contain complex parts that may occasionally break down and can be challenging to replace promptly. We appreciate your understanding.
Stay Longer For Less!
Book 3 nights and receive the 4th for free, or book for 5 nights and receive 2 additional nights for free on selected villa-only stays. With the flexibility to arrive any day of the week, your dream vacation is just a reservation away.
Offer valid on new bookings only.
Subject to availability at time of booking. Terms and Conditions apply.
Contact us today to book!
Travel between 28 Apr 2025 and 01 Nov 2025
Reviews
Truly Unforgettable!
Our stay at Tradewinds Villa in the Tryall Club was truly unforgettable. From the moment we arrived, we were welcomed with warmth and professionalism by the entire staff. The villa itself is stunning — spacious, beautifully maintained, and set in one of the most serene locations in Jamaica. The chef exceeded our expectations every day with thoughtfully prepared local meals that were as delicious as they were beautifully presented. Currry goat, oxtail, brown stew, ackee and salt fish, callaloo, porridge, fresh fruits…every dish was tailored to our tastes and dietary preferences — a true culinary experience we’ll be talking about for a long time. Housekeeping kept the villa immaculately clean with great attention to detail. From fresh linens to perfectly tidied common spaces, we always returned to a spotless and comfortable environment. The real anchor of our stay was the house manager, who oversaw everything seamlessly. Attentive without being intrusive, they made sure every part of our visit ran smoothly — coordinating meals, transportation, and activities effortlessly. We also want to commend the driver provided by the villa, who was not only friendly and professional but ensured we got to all of our destinations safely and on time. It made a huge difference having reliable transportation we could count on throughout our stay. We’re already looking forward to returning!
Great Vacation
We stayed at Tradewinds last May and has such a blast. Our kids loved the pool and the villa was just perfect for us. The staff are just so friendly, it made our stay extra special. I would highly recommend the villa and the resort.
Amazing!
Amazing!!! House was a little dated but staff made up for it. Perfect weather too. All went perfectly. Thanks again!
We had a wonderful time at Tradewinds.
Hi Emma, We had a wonderful time at Tradewinds. The house is exactly as advertised and the staff was like family by the time we left. We really liked Tryall as well. Also appreciated your services – so much in fact that we are already planning another trip and would like your help again! Thanks so much.
We had a great time
We had a great time and had to mention what a fantastic job the staff at Tradewinds did. Every meal prepared by Vincent was a winner and Gina was superb on every level -- patient, organized, welcoming and funny.
See what our experts have to say about this property.
Special Offers
Stay Longer For Less!
Book 3 nights and receive the 4th for free, or book for 5 nights and receive 2 additional nights for free on selected villa-only stays. With the flexibility to arrive any day of the week, your dream vacation is just a reservation away.
Offer valid on new bookings only.
Subject to availability at time of booking. Terms and Conditions apply.
Contact us today to book!
Travel between 28 Apr 2025 and 01 Nov 2025
Expert Reviews
Elegant seaside living
Tradewinds has one of the best locations in Tryall Club and I was treated to an entire evening here. We were completely spoiled by the incredible staff and we dined, listening to the sounds of the birds and the sea, in total comfort and luxury. I especially loved the separate bedroom/cottage by the pool, opening not one set, but three sets of French doors to the amazing views of surrounding nature would be my dream start to any day!
By Alannah Harrington From Exceptional Villas
Ticks all the boxes
I love this property and recently had the pleasure of visiting and enjoying dinner here! Tradewinds offers everything – a seafront location, refreshing sea breezes, incredible staff, and the epitome of luxurious living and comfort. The staff at all our villas in Jamaica are what truly make your holiday unforgettable, and Tradewinds is no exception. Chef David's dinner was exceptional, and butler Sean made sure we wanted for nothing. A family of pelicans perches in the trees at the front of the property, and watching them swoop and dive for fish is simply mesmerizing.
By Noreen Harrington From Exceptional Villas
Inquire About Villa
- Alannah Harrington
- Villa Specialist for Jamaica
- [email protected]
Our team know each destination and every villa we feature.
We also offer a personalized and fully complimentary concierge service so every part of your trip will be taken care of ensuring you have a hassle free vacation.
We look forward to hearing from you.
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- Type: Villa
- Sleeps: 8
- Bedroom(s): 4
- Bathroom(s): 4
- Board: Catered
-
- Long term rentals: No
- Pets: No
- Children: Yes, great for kids
- Wheelchair: No
- Eldery or infirm: Not suitable
-
- Holiday type: Family, Fully Staffed, Golf Villas, Ocean Front, Resort, Sea Views, Walk to Beach