Tradewinds at the Tryall Club

Caribbean / Jamaica / Montego Bay

Tradewinds was completely renovated and refurbished in January 2018. This amazing sea front property sits on two acres at the famous Tryall Club – directly on the Caribbean Sea. 300 feet of waterfront from the north perimeter of the property, and it is one of the newest premier villas at The Tryall Club.

up to 4
up to 8
Min. Nights Upon Request


  • 4-bedroom contemporary beachfront villa
  • 4 1/2 bathrooms
  • magnificent views of the Caribbean Sea
  • full staff: chef, butler, housekeeper, laundress, gardener
  • heated infinity edge, zero entry pool
  • hot tub for 10
  • ocean access, outdoor shower
  • ocean edge dining area for 8
  • table tennis
  • lawn games including bocce, croquet and horseshoes
  • sitting room with comfy seating & 75-inch curved TV
  • air-conditioned media room & well equipped bar area with a 65-inch curved TV
  • Sonos sound system throughout (inside & out)
  • covered veranda dining room & large seating area with automated blinds, and a 75-inch curved TV
  • water sports nearby including kayaks, paddleboards and snorkel gear (at Tryall Club beach)
  • two complimentary golf carts: one 4-seater and one 6-seater
  • The Tryall Club membership: complimentary beach, pickle ball, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room for all ages, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night.
  • Tryall Club Temporary Membership Fee (due at check-in, see paragraph below)*

Tradewinds is a cozy beachfront villa. Recently completely refurbished (finished in January 2018), the villa boasts not only a new verandah facing the sea, where the sea can be as smooth as glass. Sometimes its waves break dramatically against the sea wall.

To the east of the house is a large grassy lawn, wonderful for children's games. The beach club, pro shop, driving range, first tee, and casual beach bar and restaurant are a three-minute walk or a one-minute golf cart ride.

The dramatic entrance with double height, double doors welcomes you into the villa, which has been tastefully decorated with hues of blue and green throughout, and leads you onto the new verandah with the azure blue Caribbean Sea as its backdrop. The outside living space features an oversized L-shaped comfy sofa, and a curved 75-inch TV for keeping up with your favorite sports. The whole area has automatic screens to protect you from breeze, rain or sun.

In the main house, there are three comfortable bedrooms (two which interconnect, making a perfect fit for families with small children) and bathrooms, two of which feature outside showers and one a soaking bath tub. The cottage, which is poolside, features a king-size bed with indoor/outdoor shower.

The comfortable sitting room, with curved 50-inch TV & formal dining room open to the verandah from three double doors, through sliding pocket doors is an air-conditioned media room & bar and a 75-inch curved TV, also opening to the pool terrace.

The pool terrace features a zero entry, heated, salt water, infinity edge pool with a hot tub. There are sumptuous long sun chairs and a thatched gazebo with a double sun chair for afternoon snoozes!

The location is very private.  The service is excellent. Tradewinds is a contemporary, bright villa with plenty of natural light from the many sets of French doors, with stylish furnishings & interiors, inside, outside living at its very best.


All bedrooms have quiet remote control air conditioning, ceiling fans, flat screen HD televisions and en-suite bathrooms, robes & personal safes.

Master Bedroom
Kingsize bed, 50-inch TV, and office/den with TV and sofa. En-suite bathroom with TV, double vanity, walk-in rain shower & open-air shower. Opens to sea-facing veranda.

Bedroom 2
Kingsize bed. 50-inch TV. En-suite bathroom with double vanity, walk-in shower & open-air shower. Oceanview verandah.

Bedrooms 2 & 3 are appropriate for families as parents and children can share this two-bedroom connecting suite of rooms. 

Bedroom 3
Kingsize or twin beds at guests' option. 50-inch TV. En-suite bathroom with walk-in shower & deep tub. Opens to ocean-facing verandah.

The Cottage (Bedroom 4)
Kingsize bed. 50-inch TV. En-suite bathroom with walk-in shower & open-air shower. Opens to pool terrace. This bedroom is in a separate octagonal cottage on the edge of the pool terrace and just 20 feet from the main house.  Six French doors and 10 louvred windows open to a wonderful ocean view.

Tryall Club Membership

A significant amenity for guests in this villa is membership at the excellent Tryall Club. On 2,200 acres, Tryall’s golf course is among the most beautiful in the world. Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events. The resident pro offers workshops and private lessons. The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call. All white attire required. (Some Tryall Club golf services subject to a 15% service charge, including green fees, golf cart rentals, shoe and club rentals).

The beach is well planned for parents and children. Have lunch at the beach bar. Work out in the well-equipped gym. Jog the marked trails. Snorkeling, kayaking, hobie cat and sunfish are complimentary. Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees. Enjoy weekly events like the Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

On the hill, enjoy the historic Great House for afternoon tea and a magnificent view from the terrace. Shop at the commissary and boutique, meet for happy hour at the bar, and browse a wealth of Jamaican, Haitian and Cuban works and souvenirs in the Gallery of West Indian Art. And don’t miss the massive Tryall pool!

Membership Fee

Tryall is a private club whose members may use most Club facilities at no charge with the exception of tennis shop, ball boys, bar & restaurant, spa, grocery, motorized watersports, Nanny services and golf. Complimentary amenities include the beach, non-motorized watersports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party and various special events.

The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee of US$130 (plus 15% service charge) per week for each guest 16 years and over, or US$26 (plus 15% service charge) per day per person for stays of less than 7 days.

Plan to pay your Temporary Membership Dues locally at the Front Desk in the Great House when you register. Credit cards are accepted. You will be given a temporary membership card to enable your access to all Club facilities.

Tryall Club Front Desk will set up a charge account for you during your stay. If you plan to pay for your charge account in cash at the end of your stay, they will request a cash deposit. If you plan to pay for your charge account with a credit card, they will place a hold on your card to cover this amount (recommended hold amount is US$150 per adult per day). 

Please note: There may be occasion that some or all the facilities for the hotel may be closed for membership guest services due to a private hotel event. The Tryall Club reserves the rights to change or alter their membership packages with no advance notice.


4 Bedrooms, 4 Bathrooms

Sleeps 8 Guests

4000 Interior Square Ft.

  • Playground Nearby
  • Kids Club Membership
  • Connecting Bedroom(s)
  • Golf Nearby
  • Wireless Internet Access
  • Hot Tub (Outdoor)
  • Heated Pool
  • Infinity Edge
  • Zero Entry
  • Snorkel Gear
  • Paddle Boards
  • Kayaks
  • Water Sports Nearby
  • Tennis Nearby
  • Butler
  • Housekeeper
  • Laundress
  • Gardener
  • Full Gym Nearby
  • Tryall Club
  • Located on Club Grounds
  • Hair Dryers
  • Outdoor Shower
  • Ocean Edge Dining
  • Air-Conditioned Media Room
  • Two Complimentary Golf Carts
  • Ping Pong
  • Bocce
  • Croquet
  • Horseshoes
  • Sonos Sound System


Pool Details

30x36-feet, heated, saltwater, ocean edge

Distance Details

Beach: 3 minutes via complimentary golf cart to Tryall Club beach
Town: 25 minutes via driver
Airport: 25 minutes (MBJ)

Rates and Availability

Tax Service Charge Details*
A 10% Government Consumption Tax and Non-Refundable 5% Tryall Club Administration Fee applies to the villa rental.
Security Deposit Details
US $99 Damage Deposit Waiver Fee: A US $99 Damage Deposit Waiver Fee applies to your reservation. It is our goal to ensure that you have a remarkable experience at our villas. And we understand that accidents happen. In lieu of a large security deposit, your reservation will include a $99 Accidental Damage Waiver fee. This will cover accidental damages of up to $2,000 that occur during your stay.

The Tryall Club will collect a security deposit on arrival. If no damage occurs, your security deposit will be refunded and credited to your account. However, if damage does occur, we will reimburse you for any amount which does not exceed US$2,000.
Accidental Damage Waiver
A $99 Accidental Damage Waiver applies to every reservation.
Check-In Times
Check in: 3:00 PM - Check out: 11:00 AM
Rate Policies
A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas and New Year’s Eve.
Surcharge for festive bookings
5% surcharge for festive bookings

Exclusive Offers

Take your vacation to the next level, with 2 free airline tickets.* For a limited time, every reservation over $50,000 will receive an airline reimbursement worth up to $1,000 - any airline, any destination. Imagine flying in style to your handpicked villa located in one of the most beautiful destinations around the world, knowing that you've saved on the cost of your flights. This is your chance to experience the ultimate in luxury travel and indulge in the vacation of a lifetime.

*Free air promotion is valid new bookings only and cannot be applied to existing bookings. Valuation based on two round trip tickets using the bureau of Transportations U.S. average flight price for 2022. Receive up to a $1,000 reimbursement for flights upon presentation of a flight receipt. Minimum booking value of $50,000 applies. The booking value applies to the villa cost only and does not include any additional services or fees. This offer is valid for bookings made 2/20/2023 through 3/26/2023 for travel now through 2/31/2024. Bookings made outside of this period will not be eligible. The $1,000 air credit offer is non-transferable, has no cash value, and cannot be redeemed for any other service. The airline credit will be applied to your booking once your villa rental has been paid in full. The airline credit will be redeemed by providing a receipt of your booked flight and a check will be sent to you within 15 business days of providing flight documentation. All offers are subject to availability. We reserve the right to modify or cancel this promotion at any time without notice.



Dear Linda,

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.

Bill F.

Tradewinds has under gone a top to bottom renovation and it is stunning. The heated pool and hot tub were a hit, but Chef David and the Butler Sean really stole the show! Each meal was better than the next and Sean could not have been more welcoming and professional. The entire staff and this amazing villa truly exceeded our expectations

Doug S.

Villa information may change without notice and should be confirmed with our villa rental specialists.