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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


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 colours 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 master bedroom has a separate small sitting room with the most idyllic sheltered view over the bay.

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!

At The Tryall Club, the team is committed to continually improving their services and offerings to ensure that guests have the best possible experience during their stay. The Tryall Club is a private members club, so all guests 13 years of age and older are required to take out a Temporary Membership, which will be charged upon arrival at check-in.

Temporary Membership Dues now start at USD $32 per day, plus a 15% service charge, for guests ages 16 years and older who stay for one to four days. For guests who stay for five to seven days, the Temporary Membership Dues are now US $160 plus a 15% service charge. Children between the ages of 13 and 15 pay at a discounted rate of 50% plus a 15% service charge. For children 12 years and younger, Temporary Membership Dues are complimentary.

Includes 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 various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, Reggae Nights & Beach Parties on selected nights.

• 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
• Children Welcome
• Indoor/Outdoor Dining
• Safe
• Games available
• Flat screen SMART Televisions throughout

Area description

Read more about the Tryall Resort


Montego Bay
Nearest airport Montego Bay Airport
17 km
Nearest beach Tryall Private Beach 100 meters


  • 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 is on a request basis - please Enquire


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 2,286 - $ 4,857 $ 16,000 - $ 34,000 5 Nights -
Low Season 2024 20-Apr-2024 - 02-Aug-2024 $ 2,414 $ 16,900 5 Nights -
Low Season 2024 03-Aug-2024 - 01-Nov-2024 $ 2,286 $ 16,000 5 Nights -
Low Season 2024** 02-Nov-2024 - 13-Dec-2024 $ 2,414 $ 16,900 5 Nights -
High Season 2024 14-Dec-2024 - 20-Dec-2024 $ 3,143 $ 22,000 7 Nights -
Festive Season 2024 21-Dec-2024 - 03-Jan-2025 $ 4,857 $ 34,000 14 Nights -

Additional Information


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.

**Thanksgiving may be charged at Premium rate.**


Great Vacation
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.

By The Harris family

Amazing!!! House was a little dated but staff made up for it. Perfect weather too. All went perfectly. Thanks again!

By Outlaw Party
We had a wonderful time at Tradewinds.
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.

By Johnson Party
We had a great time
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.

By Bill F. Party
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Alannah Harrington

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.

    • 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