Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29
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Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29
Sandy Bay, Hanover, Jamaica
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Amenities
Golf course
Pool
Snorkeling
Hiking
Gym
Basketball court
Tennis court
Billiards room
All amenities
Property Description
Fall stays are now discounted 20% until November 29, with complimentary club membership fees for all villa guests (
Tradewinds is on the Caribbean Sea, with an acre of property on 380 feet 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 just 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.About pets:No pets allowed.About checkOut:Check out before 11:30 AM.About children:Children allowed: ages 0-17.Tradewinds staff is not responsible for childcare..About customRules:The villa staff is
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10.0/10
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 2 reviews
Surroundings
Airport: Sangster International Airport
(23.0 km)
Train: Jamaica Rail Way Corp.
(19.4 km)
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Overview
Rooms
Guest Reviews
Services & Amenities
Policies
Host
10
4 Bedrooms Private Vacation Home
4 bedrooms: 2 single beds and 4 king beds
Non-smoking
Check Availability
Guest Reviews
10.0/10
Outstanding
2 reviews
Verified Reviews- Cleanliness10.0
- Amenities10.0
- Location10.0
- Service10.0
Average for similar properties in Sandy Bay
Book now and leave a review after your stay to earn up to 120 Trip Coins (approx. TWD 36). Trip Coins can be used to save instantly on room rates.
Samantha L.
December 8, 2023
Paradise for Thanksgiving
My family traveled to Tradewinds for Thanksgiving 2023 and had a trip of a lifetime. Our group consisted of myself + husband, our 2 1/2 year old son, our 6 month old daughter, and my in-laws.
We got married at Round Hill in 2019, and finally made our way back to the wonderful island of Jamaica to share this special place with our children. We decided to stay at Tryall Club after finding the Tradewinds property on VRBO ... nothing short of perfection! A beautiful home w/ a pool + private beach, across from the golf course and walking distance to the beach club? It doesn't get better than this. We had an incredible 6 days at Tradewinds, and it was all made possible by the exceptional staff. We were treated like royalty/family. I was nervous to travel with two young children, but not only did they have the best time, mom + dad were able to thoroughly enjoy themselves as well. I hope our family can return to Tradewinds for years to come!
A special thank you to the staff, and Terri, the house owner. We are forever grateful for you sharing your beautiful home with us, and we cannot wait for our next trip. Sending our love from chilly NYC! PS - ask chef Todd to make Carolina Shrimp Pasta (Terri's favorite) ... it is UNREAL!!!
Love,
The Larsen Family
Susan H.
April 2, 2023
Paradise
The house, the water, the staff, the resort, sun, ease of travel, arrival/departure….all contribute to a prefect vacation. But what makes Tradewinds THE most perfect vacation is the comfortable house nestled at the foot of the Caribbean Sea and the outstanding staff. Three generations found comfort, fun, and immense pleasure at Tradewinds. Lots to do for the kids, 5-11,: snorkeling, tennis, golf, nature hike, swimming, banana boat, glass bottom boat, etc. Parents and grandparents were beyond happy and will definitely return. Kids are already asking “when.”
Services & Amenities
Most popular amenities
Golf course
Pool
Snorkeling
Off-site
Hiking
Off-site
Gym
Basketball court
Off-site
Tennis court
Billiards room
Table tennis room
Car rentals
Wi-Fi in public areas
More Amenities
Internet
Wi-Fi in public areas
Pool
Heated pool
Transportation
Car rentals
Front desk services
Concierge service
Health & wellness
Billiards room
Table tennis room
Kayaking
Sailing
Off-site
Water sports equipment
Basketball court
Off-site
Tennis court
Golf course
Hiking
Off-site
Snorkeling
Off-site
Gym
Activities
Beach towels
Table soccer
Gaming area
Fishing
Off-site
Public areas
BBQ
No smoking in public areas
Garden
Cleaning services
Clothes dryer
Facilities for children
Children's toys
Accessibility
Stair-free main entrance
Property Policies
Check-in and Check-out Times
Check-in: after 15:30
Check-out: Before 11:30
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.
Age Requirements
The main guest checking in must be at least 25 years old
Property host
About this property
Fall stays are now discounted 20% until November 29, with complimentary club membership fees for all villa guests (
Tradewinds is on the Caribbean Sea, with an acre of property on 380 feet 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 just 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.About pets:No pets allowed.About checkOut:Check out before 11:30 AM.About children:Children allowed: ages 0-17.Tradewinds staff is not responsible for childcare..About customRules:The villa staff is
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Frequently Asked Questions
What’s the cancellation policy at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29?
The cancellation policy at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29 depends on your room type and booking terms.What’s the cancellation policy at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29?
What are the check-in and check-out times at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29?
Check-in at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29 starts from 15:30, and the standard check-out time is by 11:30.What are the check-in and check-out times at Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29?
How do I get to Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29 from the nearest airport?
The nearest airport is Sangster International Airport, located about about 32 mins from hotel by car (23.0 km) away.How do I get to Tradewinds,Tryall Club,Thanksgiving Open, Discount & Comp Member Fees 'Til 11-29 from the nearest airport?
About This Property
| Nearest Airport | Sangster International Airport |
|---|---|
| Distance to Airport | 23.04KM |
| Nearest Train Station | Jamaica Rail Way Corp. |
| Distance to Train Station | 19.44KM |
| Hotel Star Rating | 4 |


