Fairwinds
Overview
Specials
Amenities
Location

Fairwinds

8 Guests
4 Bedrooms
6 Beds
4 Bathrooms
2 floors
Tryall Club, Montego Bay, Jamaica, Caribbean
Villa
Ocean View
Pool
Hot Tub

Special Offers

One Love Lives
The spirit of Jamaica endures and welcomes you back. Book this home and enjoy $250 in savings on stays through the end of April. Beautiful surroundings, warm hospitality, and the rhythms of the island await your return.
Offer applicable:
Stay: Feb 7 — Oct 31, 2026
Jamaica Escape - Stay 4 Nights for the Price of 3

Trade the everyday for turquoise waters, warm island breezes, and unforgettable sunsets. For a limited time, enjoy one complimentary night in your fully staffed villa when you book a four-night stay in beautiful Jamaica.

*Full non-refundable payment required at time of booking. No Tryall Temporary Membership Dues will be applied to the free night in this promotion.
Offer applicable:
Stay: Jun 6 — Oct 31, 2026 · Book: Feb 14 — May 31, 2026
Jamaica Escape - Stay 7 Nights for the Price of 5

Trade the everyday for turquoise waters, warm island breezes, and unforgettable sunsets. For a limited time, enjoy two complimentary nights in your fully staffed villa when you book a seven-night stay in beautiful Jamaica.

*Full non-refundable payment required at time of booking. No Tryall Temporary Membership Dues will be applied to the free night in this promotion.
Offer applicable:
Stay: Jun 6 — Oct 31, 2026 · Book: Feb 14 — May 31, 2026

About This Property

Surrounded by a tropical garden, Fairwinds offers excellent sea views, imaginatively designed gardens and a charming laid back Jamaican style.

Fairwinds offers rustic charm, amazing views, lovely gardens and two peaceful fresh water lily ponds with goldfish

Fairwinds was designed and built by the renowned architect Robert Hartley and features Caribbean architecture with delightful whimsical highlights. Located on Copperwoood Ridge , the two-tier floor plan takes advantage of excellent sea views. It is also an easy stroll down to the tennis courts and the gym.

The master bedroom is fitted with a king size bed and an en suite bathroom with a Jacuzzi tub. A secondary master bedroom has a king bed and its en suite bathroom features a unique sunken Roman Bath. Both of these master bedrooms enjoy private entrances and private patios. The guest bedrooms each have twin beds which can be configured to a king if required. These rooms also have private entrances and private patios and another (regular size) sunken Roman Bath.

The living room, the covered alcove by the pool and the pool deck all benefit from views. Dining can be either indoors or under the stars.

You will be welcomed by your private staff comprised of a Cook, housekeeper, laundress and gardener.

The Tryall Club Experience
Guests of this villa enjoy access to the prestigious Tryall Club, set across 2,200 acres of beautifully landscaped hillside and beachfront. Amenities include the renowned 18-hole championship golf course, tennis courts (day and night play), private beach club, fitness center, jogging trails, Kids Club, and complimentary non-motorized watersports such as snorkeling, kayaking, and sailing. Guests also enjoy afternoon tea at the Great House and weekly social events including the Manager’s Cocktail Party.
*While many facilities are included, additional fees apply for golf, spa services, dining and bar charges, motorized watersports, and select special events.

Temporary Tryall Membership Dues

All villa guests are required to register for a Temporary Membership during their stay. Current rates are US$170 per person (16+) per week, or US$34 per person per day for stays under 7 days (plus 15% service charge). Children 13–15 receive a 50% discount; children 12 and under are complimentary. Fees are payable directly to the Club upon arrival.
*Please note that certain facilities may occasionally close for private events, and membership offerings and fees can be subject to change at any time without notice.

Staff Gratuity in Jamaica

All inclusive staffing in Jamaica enhances the value of a fully serviced villa stay by ensuring exceptional, personalized service while simplifying the guest experience. Villa staff, including a trained chef, cater to your unique needs and preferences during your stay. It is customary that guests in Jamaica remit staff gratuity for their villa stay. Recommended gratuity ranges from 10% of the total nightly rents (exclusive of taxes and fees) during the high season (December to April) to 15% during the low season, ensuring fair compensation for the highly skilled staff. Gratuity can be paid in US or Jamaican dollars.

Unlike other destinations where staff services are arranged and charged separately, often at a high hourly rate excluding gratuity, Jamaica’s all-inclusive staff system streamlines the process allowing guests to enjoy top-quality service with ease.

Bedrooms and Amenities

Bedrooms

Primary Bedroom
Bed: King Bed·En-Suite Bath·Hot Tub·Flat-Screen TV·Additional Seating·Private Entry·Direct Access to Private Patio
Secondary Bedroom
Bed: King Bed·En-Suite Bath·Flat-Screen TV·Additional Seating·Private Entry·Direct Access to Private Patio
Bedroom Three
Bed: 2 Twin Beds w/Option as King Bed·En-Suite Bath·Flat-Screen TV·Additional Seating·Private Entry·Direct Access to Private Patio
Bedroom Four
Bed: 2 Twin Beds w/Option as King Bed·En-Suite Bath·Flat-Screen TV·Additional Seating·Private Entry·Direct Access to Private Patio

Amenities

Living Room
Sofas·Multiple Seating Areas·Flat-Screen TV·Direct Access to Deck and Pool·Ocean View
Outdoor Living
Pool·Deck·Chaise Lounges·Wet Bar·Multiple Seating Areas·Garden·Outdoor Dining Table - Seats 6·Fish Pond·Ocean View
Home Amenities
Access to Resort Amenities, Beach Club, Gym/Fitness Center and Resort Spa·Air Conditioning·Wireless/WiFi Internet Access·iPod Docking Station·CD Player·DVD Player·Safe
Transportation
2 Golf Carts·On Shuttle Route
Services Available
Chef Service·Gardener·Housekeeper·Private Laundry Service

Location

Attractions

Sangster International Airport
1.8 Miles
Nearest Airport
Aquasol Theme Park
1.7 Miles
Amusement Park, Ocean Gear Rentals, Go-Kart Racing, Water Sports
Hip Strip
1.7 Miles
Shopping & Restaurants, Sightseeing, Adventure & Exploring
Doctor's Cave Beach
2.0 Miles
Beach, Beach Club, Beach Access
Ahhh...Ras Natango Gallery and Garden
7.6 Miles
Nature Preserve, Galleries, Lookout
Round Hill Resort
10.4 Miles
Golf Course, Tennis Court, Spa, Gym, Trails, Beach Access, Kids Club
Tryall Club
13.8 Miles
Beach, Restaurants, Golf Course, Kids Club
Appleton Estate
37.4 Miles
Historic Area, Tours
Kool Runnings Waterpark
45.0 Miles
Amusement Park, Water Park
Royal Palm Reserve
48.1 Miles
Botanical Garden
$1,000 — $2,857 / night
Fairwinds
Tryall Club, Montego Bay, Jamaica, Caribbean
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8   4
$1,000 — $2,857 / night
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This property requires our Villa Specialists to confirm availability for you. Please inquire below.

For assistance call us at 888.628.4896

Rates

Please note, quote is not inclusive of Temporary Tryall Membership Fees due at the property upon check-in. Please inquire with your Villa Specialist for current rates.