Tradewinds on the Sea, Oceanfront, Rate Discount & Comp Member Fees 8/2 - 10/31 | House in Montego Bay

Late Summer to Fall stays are now discounted 20% from August 2 - October 31. This offer does not apply to previously booked dates.
Tradewinds is on the Caribbean Sea, with an acre of property & 380 ft. of waterfront. The pool, spa, terraces and a lush lawn, sprinkled with coconut palms, all border the
ocean. A private beach is present most of the day, depending on tides. Just across the quiet street is an awesome view of a pond and golf course fairways. And, the beautiful
Tryall Club beach area is a 5 minute cart ride, with a huge walk-in pool, bar, beach service, an outdoor cafe, a full service indoor restaurant, plus a boutique and
excursion & water sports centers.
Located about 30 minutes from the Montego Bay airport, The Tryall Club has 90 privately owned villas nestled into 2,000 acres of breathtaking scenery. The entire community is gated & fenced with a 24 hour security staff & cameras.
Our airport greeter (optional) will whisk you through immigration, assist you with luggage & accompany you to your van. Greeter & ground transportation reservations are made through our head of house/butler.
Every inch of Tradewinds was totally renovated in 2017/2018 including RH furnishings, electronics & systems. The landscape was transformed, with the addition of a heated infinity pool & spa. A huge ocean front veranda was also created, featuring dining & lounging areas. No expense was spared in making Tradewinds a luxury property. And, constant maintenance and recent updates (2024) keep it in great condition. Tradewinds is the perfect location for families, couples & girls/boys trips. A guest wrote that being at Tradewinds is like staying on a luxury yacht, that never moves. But, distant cruise liners, sail & fishing boats cross the water in an ever changing ocean view.
Opened for rental in 2018, Tradewinds has fabulous reviews on Vrbo & the Tryall Club's Trip Advisor page (see one from 5/25 at the end of this property description.) The main house has three bedrooms, with en suite baths. There's a fourth bedroom & bath, in a separate cottage, just next to the house. A detailed floor plan is included with the photos, on this site.
All bedrooms have exceptional sea views, exterior doors & operable louvered windows, as well as large current TVs. The primary bath, as well as #2 and #4 have indoor & outdoor showers. Bath #3 has a sea view indoor shower and a free standing bathtub. All baths have dual vanities and ample storage.
The master bedroom has a separate sitting room/office, with space for a crib. Bedroom 3 can be changed from a king to XL twin beds (with a twin to king converter.)
A second bed may be added to Bedrooms 2 or 3 (twin or queen sized.) There is no additional charge for extra beds which are high quality, with comfortable mattresses (not roll-away cots.) There's also a portable bed, which is great for two small children.
If you crave peace and privacy you'll find it at Tradewinds. With the sea to the north and the golf course, pond & hill views to the south, plus an attentive full-time staff, Tradewinds offers a rare vacation experience. But, if you want activity the resort facilities (golf, tennis, pickle ball, a gym & spa) are 5-10 minutes away, by golf cart. The
required Tryall guest membership fees are compliments of this owner, for stays of 7 nights or more. Fees are $184 per person, for 4-7 nights (for guests 16 & over.) It's $92 for those 13-15. Guests 12 and under are free.
At Tradewinds, guests will be attended to by a professional, light hearted staff of 6. The Ritz Carlton trained butler manages a villa known for unsurpassed cocktails and what's been called the best food on the island. The butler is happy to make arrangements for transportation, tours, dining reservations, etc. He sets an experienced, but casual and fun tone for Tradewinds.
Some of the many advantages of a staffed villa is choosing your own menu, dining whenever you like and dressing as you please. While food is not inexpensive in Jamaica, it's certainly less costly than dining out. Chef Todd serves 3 fabulous meals daily, with many cuisine choices, including gourmet meals and island specialties. He loves to make hors d'oeuvres, bread and outstanding desserts, so let him wow you! He strives to satisfy every guest, including those on special diets and children of all ages. Locally sourced fish & lobster are readily available, as well as organic products. Groceries can be purchased (by the staff) at a Montego Bay grocery store or at the Tryall commissary. See more details under Rules & Policies/Rental Agreement (in blue type) below your rental quote.
Morning to night housekeeping, with turndown service, and a full time laundress help to insure a relaxing stay. The gardeners keep the grounds, pool, spa and two custom golf carts (4 and 6 passenger) in top condition at all times.
As busy as they are, our staff gets rave reviews on their rapport with children. The Tryall Kid's Club, and experienced nannies, are available to give parents some time on their own. The Tryall Club recommends a 10% gratuity for the household staff for the Winter season (Christmas/New Year's Holidays through Easter Week) and 15% for the rest of the year (except Holiday season.) The gratuity is based on the net rental amount for the villa (i.e. not on hotel taxes, fees, etc.) See more details under Rules & Policies/Rental Agreement (in blue type) below your rental quote.
Bedrooms 2 & 3 have desks, and the Primary bedroom has a private sitting room, with a a desk, sectional sofa and a TV. The sitting room is just feet from the the ocean, with louvered windows on three sides. The waves lull guests to sleep at night, but sliding doors can close the sitting area off from the bedroom, if desired. The sitting room is also a great location for an in-home seaside massage, arranged by our butler, through the Tryall Spa.
Tradewinds has honed stone floors and vaulted wood ceilings. Each room/bath has a Big Ass fan, as well as air conditioners (primarily used for sleeping.) The entire house can be air conditioned, but it's rarely needed as the constant sea breeze and fans keep the house quite comfortable. The media room has a wet bar, TV, and comfortable seating. Although it adjoins the living room, sliding doors can be shut for sound protection/privacy.
The living room has 2 different ocean views, a TV, and includes a seating area with sofas and swivel chairs. Most meals are served on the veranda, but the adjacent dining area also has direct sea views. The grand veranda, with casual seating, two dining areas, and a 65" TV bridges the rear of the house, and is just steps from the sea. Automated (see through) fabric screens can be lowered if less breeze is desired.
By the heated pool, hot tub and ocean is a large thatched grass, shaded seating area. The pool is a walk-in style, with lounge chairs and built in seats for relaxing in the water. Frontgate noodles and rafts are also offered. The spa platform has the best views of a private bay, looking toward Round Hill and Montego Bay.
The house was professionally decorated, in a transitional island style. It's complete to the last detail, with high end furnishings, and lighting, Frontgate Resort bedding and bath amenities. In fact, guests frequently ask for our sheet and mattress information when they leave.
Most guests rarely want to leave Tryall, but if they do, Round Hill (a private, luxury resort) is 10 minutes away, with restaurants & bars. Very casual, seaside restaurants (in Hopewell) are about the same distance. Montego Bay has casual and fine dining restaurants, about 35 minutes away. The house butler can make reservations and arrangements for transportation.
Tradewinds provides a rare opportunity for a perfect, memorable vacation. In fact, we (the owners) went to Tryall for a birthday celebration, sold our beach house in FL and bought Tradewinds, to insure our best vacation never ended!
Trip Advisor Review 5/2025: This was our 2nd time staying at Tradewinds. What a wonderful, relaxing week! The vila, pool & hot tub are perfect for us & our grand babies. The staff is incredible and took care of our every need.
Sean, the butler took care of all our needs including travel, excursions, etc. Chef Todd delighted us with our favorite dishes: lobster, fish tacos, steak salad, eggs Benedict, etc. Gina (the housekeeper) was there from sunup to sundown, keeping the entire
villa spotless. She greeted us with cold cloths and fresh drinks after playing tennis & pickle ball. Peter, the groundskeeper, was truly a pleasure every day. He worked
quietly in the yard and villa, until we needed to adjust the hot tub and he would
miraculously appear. He was great with the grandkids. And, last, but not least,
Jennifer (the 2024 Tryall Housekeeper of the Year) is an absolute treasure. Our laundry was washed, ironed (clean smelling) & returned to our rooms. She can
remove any stain & handled our special requests with a smile. How nice to return home with all clean clothes.
In summary, it was a wonderful week in a beautiful villa, with an amazing staff. It was just what we all needed & the perfect vacation.
Enough said! Come to Tradewinds, and experience your best vacation ever!
For more details on how Tryall villas operate (services, food, etc.) go to the Tryall site (www.tryallclub.com) Select Tryall Villas and then Villa Experience. More specific details on Tradewinds are on this (Vrbo) site under Rules & Policies/Rental Agreement, which is actually guest information.) It's in blue type, below your rental quote.

This 4 Bedrooms House provides accommodation with Guest Services, Hot Tub, Internet, for your convenience. This House features many amenities for guests who want to stay for a few days, a weekend or probably a longer vacation with family, friends or group. The rental House has 4 Bedrooms and 1 Bathroom to make you feel right at home.

Check to see if this House has the amenities you need and a location that makes this a great choice to stay in Tryall. Enjoy your stay in Tryall at this House.