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Tradewinds on the Sea

Guests: 9Bedrooms: 4Bathrooms: 5

Listing Description

Email the owner for details on Fall discounts.

We’ve been to Tradewinds 5 times in 2021, with guests of all ages. Our home has also been frequently rented (primarily by Americans) with everyone having a safe, enjoyable trip. Jamaica has a tourist corridor (from Ocho Rios-Negril) for visitors to travel freely and enjoy dining, attractions, fishing, sailing excursions, etc. Our Tradewinds staff (of 6) has been fully vaccinated, as has a majority of the staff at Tryall. However, everyone continues to wear masks, as just one part of the strict Jamaican protocols.

Guests (using our VIP airport greeter) are whisked through a special immigration area, baggage claim and out to one of our waiting drivers, in a sanitized vehicle. The process for entering the country is quite simple, using the Jam Covid-19 govt. phone app. Covid tests are required within 3 days of departure, and by the US for re-entry. Departure testing is available in the villa or at the MBJ airport, the day of departure.

Tradewinds is literally on the sea; an acre of property, with 380 feet of waterfront access. 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. The Tryall golf course is just across the quiet street, with an awesome view of the lake and fairways. And, the fabulous new Tryall Club beach is a 5 minute cart ride, with a huge walk-in pool, bars, beach service, an outdoor cafe and indoor restaurant, as well as a boutique, excursion and water sports centers.

Located less than 30 minutes from the Montego Bay airport, The Tryall Club has 90 privately owned villas, nestled into over two thousand acres of breathtaking scenery.

Tradewinds was named Tryall Villa of the Year for 2019.

Each room in historic Tradewinds was completely renovated in 2017/2018 including upscale furnishings, electronics and systems. The landscape was transformed, with the addition a new heated infinity pool and spa. A huge, ocean front veranda was built featuring two dining and lounging areas, with a TV. No expense was spared in making Tradewinds a luxury property. And, constant updates and refurbishing keep it in great condition. It’s the perfect location for families, couples and girls and boys trips.

A guest wrote that being at Tradewinds is like staying on a luxury yacht, that never moves. But, distant ships, sail and fishing boats cross the waterfront in an ever changing ocean view.

On the rental market since 2017, Tradewinds has fabulous reviews, on VRBO and the Tryall Club’s Trip Advisor page (see one at the end of this property description.)

The main house has 3 bedrooms, with en suite baths. There’s a fourth bedroom and bath, in a separate cottage, right next to the main house. A detailed floor plan is included with the photos on this site. All bedrooms have exceptional sea views, exterior doors and operable louvered windows, as well as large Smart TVs. The master bath, as well as #2 and #4 have indoor and outdoor showers. Bath #3 has a sea view indoor shower and a free standing bath tub. 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 converted from a king to XL twin beds. A second bed may be added to Bedroom 2 (twin or queen sized.) There is no additional charge for the bed(s) which are high quality, with comfortable mattresses (not roll away cots.)

If you crave peace and privacy you’ll find it at Tradewinds. With the sea to the north and golf course, lake and hill views to the south, plus an attentive full-time staff, Tradewinds offers a rare vacation experience. But, if you want activity and the company of other guests and owners, the resort facilities are 5 minutes away. The required Tryall membership fees are compliments of the owner, for stays of 5 nights or more. Fees are $165 per person, for 4 nights or more (for guests over 16.) So, that’s a savings of $1,300 for 8 guests (including the 15% gratuity and taxes.)

While at Tradewinds, guests will be attended to by a professional, light hearted staff of 6. The Ritz Carlton trained butler manages a house known for unsurpassed cocktails and the “best food on the island” according to guests. The butler is happy to make arrangements for transportation, tours, dining reservations, etc. He sets an experienced, but casual and fun tone for Tradewinds.

The chef (US/Jamaica trained) serves three fabulous meals daily, with many cuisine choices. He offers gourmet meals and island specialties. He loves to make hors d’oeuvres, so let him wow you! The chef is passionate about food, and 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 may be purchased (by the staff) at a Montego Bay grocery store or at the Tryall Commissary. See the “Rental Agreement” under Rules & Policies for details.

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 (Summer 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, specifically under the Rental Agreement information.

Bedrooms 2 & 3 have desks, and the Master has a private sitting room, with a large 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 massage, arranged by the butler.

Tradewinds has honed sea 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 closed and 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. There is a pass through counter from the kitchen, which can also be closed off.

The living room has 2 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 room also has direct sea views.

A 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.

Tradewinds has a large thatched grass, shade seating area, just next to the heated pool and spa. 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, luxury bedding and bath amenities.

Most guests never want to leave Tryall, but if they do Round Hill, another private, luxury resort, is 10 minutes away, with restaurants, bars and a beautiful full service spa. Very casual, seaside restaurants (in Hopewell) are about the same distance. Montego Bay has casual and fine dining restaurants, about 30 minutes away. The house butler can make reservations and arrangements for transportation.

Tradewinds provides a rare opportunity for a perfect, memorable vacation. In fact, the owners came to Tryall for a birthday celebration, sold their beach house in Florida and bought Tradewinds to insure their best vacation never ended!

Trip Advisor Review:

Our group included myself, my wife, her mother, her brother and his family (wife, 1 year old, and two girls under 10.) We were so excited to see the updates and renovations. The heated infinity pool is amazing (gradual depth increase is great for all ages) Tradewinds also has two new golf carts (including one six-seater) which is fun to take all 6 of us at once. No expense was spared in the complete renovation, every television is a big screen/smart. Every pillow, bed linen and towel is luxury grade. Aside from the spectacular ocean front setting and renovations, the staff made the vacation. Sean, the butler, who takes care of everything (recommendations and setting up a romantic dinner, transportation, taking my mother in law to Rose Hall mansion. ) He left after dinner on our last night only to return with a pack of diapers for my brother in law’s baby, as we had mentioned we were almost out. David, the chef, prepares the best meals on the island. We felt as if we were at a 10 star restaurant every evening. The staff members help to make everything easy and comfortable. They were all wonderful with the children, and so attentive to any needs. Sean and his staff feel like part of the family. Now back in cold Michigan, we’re ready to go back to Tradewinds.

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 ( Select Tryall Villas and then Villa Experience. More specific details on Tradewinds are on this site under Rules & Policies/Rental Agreement.

Bedroom Details
Bedroom 1
1 King Bed
1 Ensuite Bathroom
1 TV
Bedroom 2
1 King Bed
1 Ensuite Bathroom
1 TV
Bedroom 3
1 King Bed
1 Twin
1 Ensuite Bathroom
1 TV
Bedroom 4
1 King Bed
1 Ensuite Bathroom
1 TV
Room Features
Beach Chairs
8 Beach Chairs
Close To
Beach Club
Diving / Snorkeling
Shopping Mall
Swimmable Beach
Free WiFi
High Speed Internet
Dining Room Chairs
6 Dining Room Chairs
DVD Player
Home Theatre
Large Flatscreen TV
Satellite TV
Stereo System
Video Game Console
Foosball / Soccer Table
Ping Pong Table
Pool Table
Golf Course Access
Golfcart Included
Handicapped Accessible
Lake View
Ocean View
Private Beach Club
Swimmable Beach
Indoor Features
Air Conditioned
Ceiling Fans
Central AC
Iron & Ironing Board
Mini Splits
Wet Bar
Zoned Air Conditioning
Coffee Maker
Gourmet Kitchen
Ice Maker
Professional Appliances
Maid Service
Daily Maid Service
Outdoor Features
Child Friendly Pool
Dining Table
Heated Pool
Infinity Pool
Outdoor Shower
Stand Up Paddle Boards
Sunning Pool
Swimming Pool
Outdoor Loungers
8 Lounge Chairs
Services Included
Chef Included
Concierge Included
Houseman Included


May 2024
June 2024
Price per night: USD$ 2,014
Minimum no of nights: 3
Terms and Conditions
Smoking Allowed
Pets Allowed
Party Allowed
Children Allowed
100% refund if you cancel at least 60 days before check-in. 50% refund (minus the service fee) if you cancel at least 30 days before check-in. No refund if you cancel less than 30 days before check-in.
You will be responsible for any damage to the rental property caused by you or your party during your stay. The villa staff is not responsible for childcare. Tryall has a kid's club and fully trained nannies (both fee based.) Guests pay the villa staff a minimum gratuity of 10% of the rental rate for the Winter & Holiday Seasons & 15% for Summer Season, at departure. Children must be supervised by parents (or Tryall nannies) particularly at the pool and waterfront areas.
from USD$ 2,014/night

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Sandie Cagata

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