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Fairwinds at the Tryall Club

What we like most
  • Surrounded by lush gardens, two freshwater lily ponds, and captivating sea views.
  • Designed by renowned architect Robert Hartley, featuring whimsical Caribbean architecture.
  • Each bedroom with private entrances and patios, providing intimate retreats.
Insider's Knowledge
  • En suite bathrooms feature a Jacuzzi tub and a sunken Roman Bath.
  • Easy stroll to tennis courts and gym for recreational activities.
  • Enjoy meals indoors or under the stars with breathtaking views.
Places close by
  • Copperwood Ridge: Explore the scenic surroundings with excellent sea views.
  • Tennis Courts and Gym: A short walk for those looking to stay active during their stay.
  • Montego Bay (12 Miles from villa)


Welcome to Fairwinds at the Tryall Club, a beautiful 4 bedroom private villa with a magnificent sea view located in the exclusive Tryall Club in Montego Bay.

Villa Fairwinds boasts meticulous attention to design and comfort which has resulted in a superb home away from home, Mahogany parquet floors, cable televisions and sound system, sunken Roman baths, a first-class chef ~ and all the amenities of the extremely exclusive Tryall Club combine to distinguish Fairwinds as one of the truly outstanding vacation homes of the Caribbean.

Throughout this luxury Jamaican villa, you will find the spectacular panorama of the manicured golf course and the translucent Caribbean Sea. From the spacious living room, glass panels open to the upstairs dining balcony where one of the best views of sunrises and sunsets can be captured. Memorable candlelight dinners are also served here with the magical romance of lighted palm trees dotting the hillside and the night light show of cruise ships and Montego Bay-like diamonds sparkling in the distance.

Guests may enjoy cable television, VCR, and a library of videos and CDs. Explore the bookshelves or enjoy an old-fashioned game night with many selections available. Villa Fairwinds has entertainment that caters for all; from family to couples, to the young and lively.

Outdoor stairways from the living room and three bedrooms lead to the large pool and poolside bar and lounge with icemaker, cable television, a stereo system, telephone and fish-filled grotto ... all under dramatic stone arches. A great place for all the family -Children love to feed the fish! Lunch is typically served outside on the lower level under the protective shade of a large ficus tree. Three acres of gardens are lush in many species of tropical flora including the orchids that surround the pool.

While private and self-contained, Fairwinds is only minutes from The Tryall's Great House, golf and tennis pro shops, bars and restaurants, shops, beach club, water sports and nighttime entertainment. The complimentary golf cart included with villa rental enables guests to explore the 2,200 acres that make up The Tryall Club.

Check out all of the wonderful things to do at the Tryall Resort Jamaica.

STAFF While staying in Villa Fairwinds you will be personally looked after by our wonderful team of staff. The staff includes our chef, housekeeper, laundress and gardener. The staff's marvellous team will cater your every need and make sure you have everything you want for your dream vacation at Villa Fairwinds.

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.

• Superior 4-bedroom 4-bathroom private villa at the famous Tryall Club
• Staff of four: cook, housekeeper, laundress, gardener - please note, no butler is among the Fairwinds staff because the staff ladies are responsible for serving drinks and meals - the quality of service will be excellent
• Private pool and covered poolside bar, wet bar, icemaker and lounge with television
• Air-conditioned bedrooms, wall safes, ceiling fans throughout
• Cable televisions in all bedrooms, living room, bar, master bedroom, children's room
• Wi-Fi is throughout the villa and a computer is located in the living room
• VCR and library of videos for parents and children
• Sound system and selection of CD's
• Complimentary wireless ADSL Internet and computer in living room
• Complimentary golf cart for excursions throughout The Tryall Club resort
• Child-friendly: portable playpen, booster seat, games, kids' videos, inflatable pool toys,
nannies on request


Master Bedroom Downstairs on Lower Level by Bar & Pool
Kingsize bed; mirrored walls framed in mahogany latticework; 8-foot Mexican-tiled sunken tub with louvred walls open to a tropical garden; television and VCR; private entrance from lower patio; glamorous, private and romantic. This is the only pool level bedroom and is accessed only via an outside stairway.

Bedroom 2
Kingsize bed; en-suite bathroom with Jacuzzi tub; sea view; private outside entrance and stairs to pool.

Bedroom 3
Optional kingsize or twin beds; sea view; en-suite bathroom with marble Roman tub; private terrace, stairs to pool.

Bedroom 4
Optional kingsize or twin beds; en-suite bathroom with tub-shower combination; private outside entrance, stairs to pool. Ideal for children (door to stairs to pool can be locked) as it is in the wing near Bedroom 2 ~ also fine for adults.

Villa Features
• 4 Bedrooms, 4 Bathrooms
• Sleeps 8 People
• 4 Staff
• Air Conditioning
• Children Welcome
• Fully Staffed Villa
• Golf Available Tryall Club (members only). Across town: Cinnamon Hill, Half Moon, White Witch
• Internet Wireless
• Pool
• Hair Dryers
• Tryall Club member located on Club grounds
• Kids Club Membership
• Playground Nearby
• Complimentary Calls to the US, UK and Canada
• Computer or Laptop
• Wireless Internet Access
• Full Gym Nearby (walk, drive or take golf cart)
• Golf on Site or Nearby
• Tennis Nearby
• Helicopter Pad
• Spa on Site or Nearby
• Kayaks

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.

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 new Usain Bolt Games Room at the Great House (teens love it). Jog the marked trails. Snorkelling, 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 the week’s events, including the Monday Night Manager’s Cocktail Party and the Wednesday and Friday night beach parties and buffets.

On the hill, enjoy the historic Great House for daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar. Also, the Great House is the new Usain Bolt Games Room open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs and HDTV. And don’t miss the massive Tryall pool (ping pong table there too). The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads and everyone from teens to octogenarians.
For a great write-up of the Tryall Club, see Dana Vachon's article Club Jamaica in Departures MagazineCondé Nast Traveler chose the Tryall Club for its Gold List of "the best places to stay in the whole world.”

Area description

Enclosed by a cradle of hills with stunning views of the western coastline, Montego Bay’s lovely beaches are just one of the reasons why it is so popular. Montego Bay is a busy place with the centre of activity centred along Gloucester Avenue which has been renamed the “Hip Strip”, bars, restaurants and gift shops line most of the avenue. The strip ends with the infamous Margaritaville and soon after this you will come to Montego Bay’s most famous beach called Doctor’s Cave Beach. At the end of the hip Strip, the sea emerges once again with a lovely stretch of beach with some great snorkelling.
Downtown Montego Bay is not touristy but great to visit if you want to get a flavour of local Jamaican culture. It can be quite chaotic and colourful with lots of fruit and vegetable markets and local shops


Montego Bay
Nearest airport Montego Bay Airport
5.1 km
Nearest beach Tryall Beach 100 meters


  • Bedroom(s): 4 ( Sleeps 8 )
    2 Double with en-suite, 2 Twin with en-suite
  • Bathroom(s): 4
    4 Baths, 4 Showers, 4 Wash basins, 4 Toilets, 1 Jacuzzi/Hot tub
  • General facilities: Bar, Ceiling Fans, Garden, Garden View, Gated Entrance, High Speed Internet, Panoramic Views, Parking, Private Location, Private Terrace, Terrace, Wifi
  • Indoor facilities: Air conditioning, All Bedrooms Air Conditioned, All Bedrooms En Suite, CD Player, DVD Player, iPOD Docking Station, Jacuzzi - indoor, TV
  • Outdoor facilities: Enclosed Garden, Parking, Patio, Private Terrace, Restaurants nearby, Sea Views, Sun Loungers, Swimming pool
  • Services: Chef Included, Cleaning inclusive, Concierge Service, Gardener, Linen provided, Maid service, Towels provided
  • Access: Off-road parking, Secure parking, Private car park


Availability is on a request basis - please Enquire


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 857 - $ 2,429 $ 6,000 - $ 17,000 5 Nights -
Summer 2024 20-Apr-2024 - 02-Aug-2024 $ 1,143 $ 8,000 5 Nights -
Summer 2024 03-Aug-2024 - 01-Nov-2024 $ 857 $ 6,000 5 Nights -
Low Season 2024** 02-Nov-2024 - 13-Dec-2024 $ 1,143 $ 8,000 5 Nights -
Low Season 2024 14-Dec-2024 - 20-Dec-2024 $ 1,714 $ 12,000 5 Nights -
Festive Season 2024 21-Dec-2024 - 03-Jan-2025 $ 2,429 $ 17,000 12 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.**


The best vacation experiences that we have ever had.
The best vacation experiences that we have ever had.

We had an awesome time at Fairwinds. It was beautiful and the staff was excellent! The staff at Fairwinds really made it one of the best vacation experiences that we have ever had.

By Pierce 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, Honeymoon, Resort, Sea Views, Walk to Beach