Fairwinds, Tryall Club

** Please drop us a message before booking the property as we need to check availability for all requests at this villa **

PROMO! Special Offer
STAY & PLAY GOLF PACKAGES 2026–2027
Championship golf meets Caribbean villa luxury
4–7 night packages from $1,900 per person

Packages valid in low season from April 25th - Nov 20th 2026 and high season from Nov 21* - April 24* 2026/27. Any day arrival applies to new bookings from April 25th to Nov 20th, 2026, only. Blackout dates include US Thanksgiving, Presidents’ Week, Christmas, New Year and Spring Break.
Prices include all local taxes, administrative fees, and the 10% service charge for villa staff. Alcoholic beverages and shrimp, lobster, speciality seafood, and selected meats are not included. Same-day replay rounds: complimentary green fee; just pay cart & caddy fees for the 2nd round. Caddy gratuity is not included.

** Full payment is required at the time of booking (non-refundable).
Terms & Conditions apply. * Supplemental St & 6th nightly rates are available.
Reserve your Stay & Play Golf Package today by messaging us.

FAIRWINDS at the TRYALL CLUB, Montego Bay, Jamaica

Fairwinds is a sophisticated Jamaican residence with breathtaking views of the Caribbean sea and lush tropical gardens. The villa’s beautiful grounds include two freshwater lily ponds teeming with goldfish, making it the ideal place to rest and reconnect. Designed by Robert Hartley, Fairwinds exemplifies the epitomy of traditional Caribbean architecture.

Located on Copperwood Ridge, the villa’s two-tier floor plan maximizes the breathtaking sea views and is a short walk to the gym and tennis courts. The primary bedroom features a king-size bed and an en-suite bathroom with a Jacuzzi tub. A secondary master also boasts a king bed and an en-suite with a unique sunken Roman bath. Both master bedrooms have private entrances and patios. The guest bedrooms come with twin beds that can be converted into kings and also feature private entrances and patios. Another sunken Roman bath is available in one of these rooms for extra relaxation.

Whether you’re lounging in the living room, enjoying the covered alcove by the pool, or soaking up the views from the pool deck, every space at Fairwinds is designed with comfort in mind.

The dedicated staff, including a housekeeper, cook, laundress, and gardener, will make your stay even more special, ensuring a seamless and unforgettable experience.

AMENITIES
• Swimming pool – deepest point 8 feet
• Indoor/Outdoor Dining
• Wet Bar, Free wifi
• Private balconies
• Cable programming,  Flat screen TVs in all bedrooms
• ‘Smart’ plasma TV in living room
• Golf carts
• Free on-property shuttle service

Features
• Short golf cart ride to the beach, golf
• Walking distance to Tennis
• Massage center
• Fitness center, Boutique
• Tryall market
• Kid’s Club &Games room

STAFF
• Chef
• Head of the House
• Laundress 
• Housekeeper
• Gardener

** All villa rates are subject to a 10% Government Tax and a 7.5% (non-refundable) Administration Fee.

Please note that villa reservations for stays from November 2026 onward will be subject to a 10% non-refundable Administration Fee.
Additionally, reservations for stays from April 1, 2027, onward will attract a 15% Government Tax.

TEMPORARY MEMBERSHIP DUES/FEES
The Club requires all villa guests to obtain a Temporary Membership for their stay. By obtaining a Temporary Membership, you gain access to all Club facilities and amenities, ensuring a memorable experience during your stay.
The Fee Structure is as follows:
The Club requires all villa rental guests to have a temporary membership for their stay.
This is $45 per day for persons over 16 year-olds, $25 per day for 13 – 16-year-olds, and complimentary for 12 years and younger.

All Temporary Membership Fees are subject to a 15% service charge. Fees may change without notice.

Payment Options: You can choose to pre-pay the membership fees or pay them upon arrival at the Club.

BEDROOM DESCRIPTION
Main
Bedroom 1 - King size bed, A/C, En-suite bathroom, Jacuzzi tub
Bedroom 2 - King size bed, A/C, En-suite bathroom, unique sunken Roman Bath
Guest Bedroom
Bedroom 3 - 2 Twin beds (which can be combined as kings), A/C, En-suite bathroom
Bedroom 4 - 2 Twin beds (which can be combined as kings), A/C, En-suite bathroom

• All rates quoted in USD.
• Rates are subject to change without notice
• Villa staff is exclusively curated and included in all villa rates.
  Tips can be paid in cash to the villa manager upon departure to distribute amongst the villa team, or you may place the amount on your Front Office account. When charged to your account this attracts a 3.5% surcharge charge.

CASH ADVANCE
If you need extra cash while on the property:
You can request a cash advance against your credit card at the Front Office.
Notice Required: A one-day advance notice is necessary, with a maximum advance of US$200 percouple per day.
A 7.5% surcharge will apply.