Tradewinds at the Tryall Club
4 Bedrooms, 4 Bathrooms, 8 Guests
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Tradewinds at the Tryall Club

Montego Bay, Jamaica, Caribbean – Vacation Rental
Villa – 4,000 sq ft. on 1 floor
4 People Looking
8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Ocean Front Pool Hot Tub Mobility Friendly


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.
  • 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, 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.

The 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. It's 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 4 Agile Turf courts and 5 Nova Cushion courts, some lit for night play, with world-class pros on call. All white attire is required.

The beach is well-planned for parents and children. Have lunch at the beach bar. Work out in the well-equipped gym and compete in the Usain Bolt Games Room at the Great House (teens love it). 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 a complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

Tryall Club Temporary Membership Dues
The Tryall Club is a private club where members may use most facilities at no charge except for the tennis shop, ball boys, bar & restaurant, spa, motorized watersports, nanny services, and golf.  Complimentary amenities include the beach, non-motorized watersports, tennis, the fitness room, 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 Dues cost of US$160 (plus a 15% service charge) per week for each guest 16 years and over, or US$32 (plus a 15% service charge) per day per person for stays of less than 7 days. Children between the ages of 13 and 15 are at a discounted rate of 50% plus a 15% service charge. For children 12 years and younger, the Temporary Membership Dues are complimentary.  

Plan to pay your TMD fee at the Front Desk in the Great House when you register (see below).
Please note: There may be occasions when 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 right to change or alter its membership packages with no advance notice.

When your driver brings you to Tryall, you will check in at the front desk. You will be asked for your passport as a means of identification. You will sign a waiver & need to provide a driving license for the use of the complimentary golf carts provided at the villa as well as any additional golf carts you may wish to rent.

The Tryall Club can set up an account for your stay.  A credit card is required at check-in and a credit hold will be placed until check-out for budgetary items & signing privileges (i.e., groceries, restaurant dining, golf, and activities). The calculated amount for the credit hold is approximately US$150 per bedroom per night. If you plan to make payment for your Folio Account in cash, they will request a cash deposit.  If you plan to make payment by credit card, they will place a hold on your credit card.

The Tryall Club will charge your credit card or take a cash payment for the Temporary Membership Dues of US$160 (plus a 15% service charge) per person per week for each guest 16 years and over, or US$32 (plus 15% service charge) per person per day for stays of less than 7 days; a discount of 50% (plus the 15% service charge) applies to children who are ages 13-15 years old.  Children 12 years and younger are complimentary.  
$2,072 - $4,786 /per night
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For assistance call us at 888.628.4896.
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Bedrooms and Amenities

Bedrooms: 4 (8 Guests)

Master Bedroom
Bed: King Bed • En-Suite Bath with Walk-In Shower and Dual Vanity • Air Conditioning • Direct Access to Veranda • Flat-Screen TV • Ceiling Fan • Safe • Office Area
Bedroom Two
Bed: King Bed • En-Suite Bath with Walk-In Shower and Dual Vanity • Air Conditioning • Direct Access to Veranda • Flat-Screen TV • Ceiling Fan • Safe • Connecting/Adjoined Room *
Bedroom Three
Bed: 2 Twin Beds w/Option as King Bed • En-Suite Bath with Walk-In Shower and Bathtub • Air Conditioning • Direct Access to Veranda • Flat-Screen TV • Ceiling Fan • Safe • Connecting/Adjoined Room *
The Cottage - Bedroom Four
Bed: King Bed • En-Suite Bath with Walk-In Shower • Air Conditioning • Direct Access to Terrace and Pool • Flat-Screen TV • Ceiling Fan • Safe

Living Room
Sofa • Flat-Screen TV • Additional Seating • Direct Access to Terrace and Pool • Ceiling Fan
Fully Equipped Kitchen Stainless Steel Appliances, Gas Stove • Dishwasher • Coffee Maker • Toaster
Dining Area
Dining Table - Seats 6 • Open Concept
Media Room
Sofa • Flat-Screen TV • Wet Bar • Direct Access to Terrace and Pool • Air Conditioning • Additional Seating
Pool Terrace
Heated, Salt Water Pool • Hot Tub • Fully Furnished Terrace • Direct Access to Beach • Chaise Lounge w/Cushions • BBQ Grill • Multiple Seating Areas • Dining Table - Seats 8
Covered Veranda
Sofa • Dining Table - Seats 10 • Flat-Screen TV • Direct Access to Patio • Multiple Seating Areas
Home Amenities
Wireless/WiFi Internet Access • Sound System * • 2 Golf Carts *
Services Included
Chef Service • Butler Service • Housekeeper • Gardener • Private Laundress
Tryall Club Membership (Additional Fee)
Access to Beach Club • Access to Tennis Court • Access to Gym/Fitness Center • Access to *

Area Attractions

Sangster Int'l Airport: Montego Bay
28.3 kilometres
Nearest Airport, Airport
Tryall Club
2.0 kilometres
Beach, Restaurants, Golf Course, Kids Club
Jungle Zip Lining
9.4 kilometres
Zip Line
Aquasol Theme Park
20.3 kilometres
Amusement Park, Ocean Gear Rentals, Go-Kart Racing, Water Sports
Montego Bay
28.3 kilometres
Shopping & Restaurants
Discovery Bay
85.6 kilometres
Shopping & Restaurants
Dunn's River Falls
115.6 kilometres


Please note that the holiday (higher) nightly rate will be applicable to the full duration of any reservation that includes said holiday date, regardless of rate period listed.


April 15 - November 17
$2,072 / night
$14,500 / week
November 18 - November 25
$2,786 / night
$19,500 / week
November 26 - December 15
$2,072 / night
$14,500 / week
December 16 - December 23
$2,786 / night
$19,500 / week
December 24 - January 5, 2024
$4,429 / night
$31,000 / week


January 6 - April 15
$3,143 / night
$22,000 / week
April 16 - November 22
$2,286 / night
$16,000 / week
November 23 - November 30
$3,143 / night
$22,000 / week
December 1 - December 15
$2,286 / night
$16,000 / week
December 16 - December 23
$3,143 / night
$22,000 / week
December 24 - January 5, 2025
$4,786 / night
$33,500 / week

Pricing Notes:
Prices do not include applicable taxes and fees. All rates and fees are subject to change without prior notice. For more information, please contact your EEI Vacation Estate Specialist.


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