Entire home

Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available

Savor gourmet island cuisine in your own seaside paradise or indulge in refreshing cocktails at the poolside bar.

Photo gallery for Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available

Outdoor pool, a heated pool
Exterior
Outdoor pool, a heated pool
Fridge, microwave, oven, stovetop
Smart TV, DVD player, foosball, table tennis

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 9372 sq m

Popular amenities

  • Hot Tub
  • Parking available
  • Washer
  • Gym
  • Pool
  • Barbecue grill

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available



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 lake 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, plus a boutique and excursion & water sports centers.

Located 35 minutes from the Montego Bay airport, The Tryall Club has 90 privately owned villas, golf, tennis, a spa, bars, etc. nestled into 2,000 acres of breathtaking scenery. The entire community is gated and fenced with a 24 hour security staff.

Our airport greeter (optional) will whisk you through immigration, assist you with luggage & accompany you to your van. Greeter and ground transportation reservations are made through our head of house/butler.

Every room in Tradewinds was totally renovated in 2017/2018 including RH furnishings, electronics and systems. The landscape was transformed, with the addition of a new heated infinity pool and spa. A huge ocean front veranda was added, featuring dining and lounging areas. No expense was spared in making Tradewinds a luxury property. And, constant maintenance and recent updates (in 2022 & 2023) 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.

Open for rental in 2018, 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 three bedrooms, with en suite baths. There's a fourth bedroom and bath, in a separate cottage, right 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 Smart 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 the bed(s) which are high quality, with comfortable mattresses (not roll-away cots.) We also have 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, lake & 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 (including golf, tennis, pickle ball & a gym are 5-10 minutes away, by golf cart.) The required Tryall membership fees are compliments of the 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 a chef who offers 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.

One 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. The chef serves 3 fabulous meals daily, with many cuisine choices. He offers gourmet meals and island specialties. He loves to make hors d'oeuvres, bread and 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 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 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.

Tradewinds has a large thatched grass, shaded 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. In fact, guests frequently ask for our sheet and mattress information when they leave.

Most guests never 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: Our group included myself, my wife, her mother, her brother and his family (wife, 1 year old, and two girls under 10.) The heated infinity pool is amazing (gradual depth increase is great for all ages.) Tradewinds also has two golf carts (including one six-seater) which is fun to take all 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, to return with a pack of diapers for my brother in law's baby, as we had mentioned we were almost out. 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 (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.

Property manager

Terri Johnson

Languages

English

Property amenities

Beach

  • On the beach
  • Beach towels
  • Beach sun loungers

Pool/Spa

  • Private pool
  • Outdoor pool
  • Heated pool
  • Shared/communal pool
  • Hot tub
  • Massages

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking
  • Limo/town car service
  • Car not required

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Lobster/crab pot
  • Electric kettle
  • Blender
  • Paper towels

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 1.5 bathrooms
  • Shower
  • Towels provided
  • Hair dryer
  • Soap
  • Outdoor shower
  • Shampoo
  • Toilet paper

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite service
  • Pool or billiards table
  • Foosball table
  • Table tennis
  • Arcade/game room
  • DVD player
  • Stereo
  • Video library
  • Music library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer

Work spaces

  • Office

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessible
  • Smoke-free property

Services and conveniences

  • Concierge services
  • Limited housekeeping
  • Safe
  • Chef
  • Iron/ironing board
  • Phone

Location highlights

  • Near the ocean
  • Near the sea
  • On the lake
  • On the waterfront
  • Near a health or beauty spa
  • Near the bay

Things to do

  • Fitness center
  • Fitness facilities nearby
  • Golf privileges
  • Water sports equipment
  • Boat on site
  • Golfing on site
  • Kayak on site
  • Tennis on site
  • Water skiing nearby
  • Rafting nearby
  • Kayaking nearby
  • Hiking/biking trails nearby
  • Basketball nearby
  • Fishing nearby
  • Power boating nearby
  • Swimming nearby
  • Birdwatching nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 4000 sq ft (372 sq m)

Similar properties

Policies

Check-in

Check-in time starts at 3:30 PM
Minimum check-in age: 25

Check-out

Check-out before 11:30 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Tradewinds staff is not responsible for childcare.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 50
Note from host: Large events must be managed by the Tryall Club.
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is not required for transportation to and from this property

Property is also known as

Tradewinds on the Sea Tryall Club Complimentary Club Fees

About the neighborhood

Map
Montego Bay, Hanover Parish

What's nearby

  • Tryall Golf Club - 1 min walk
  • Montego Bay Cruise Ship Terminal - 18 min drive
  • Freeport Peninsula - 19 min drive
  • Sunset Beach Resort Au Natural Beach - 20 min drive
  • Doctor's Cave Beach - 32 min drive

Getting around

  • Sir Donald Sangster Intl. Airport (MBJ) - 41 min drive

Restaurants

  • ‪the jerk hut at Grand Palladium - ‬11 min drive
  • ‪Roselle Bar - ‬11 min drive
  • ‪COLD BEER JOINT - ‬8 min drive
  • ‪Seaside Terrace - ‬8 min drive
  • ‪Mosquito Cove - ‬5 min drive

Frequently asked questions

Does Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available?

Check-in begins at 3:30 PM.

What time is check-out at Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available?

Check-out is at 11:30 AM.

Where is Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available located?

Nestled on the beach, this Sandy Bay vacation home is within a 5-minute walk of Tryall Golf Club and Jamaica Beaches. Chukka Ocean Outpost at Sandy Bay is 2.2 mi (3.5 km) away.

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Tradewinds, Tryall Club, Oceanfront, Comp Resort Fees, April 5-12 Available Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 26 out of 26 reviews
Rating 8 - Good. 0 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Colin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding Villa and Staff
Wonderful luxury villa on the sea in the Tryall resort. Outstanding staff of six. Delicious meals
Stayed 7 nights in Apr 2024

10/10 Excellent

Mika S., Minneapolis, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Vacation
From the moment we arrived and were greeted by the staff, we knew we were in for a special vacation. The property is immaculate, the staff is wonderful, and the Tryall Club resort is breathtaking. You can’t beat the views of Tradewinds; the sound of waves was the perfect way to fall asleep every night. We hope to be back soon!
Stayed 5 nights in Feb 2024

10/10 Excellent

Tim S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House, excellent location, awesome ataff
5 stars. Exactly as advertised, pictured. Entire house staff was great! Looks like a great beach club being constructed as well.
Stayed 5 nights in Nov 2023

10/10 Excellent

Kim L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
From Almost Heaven to Heaven!
Three West Virginia gals ventured to Jamaica and stayed at Tradewinds…and we were blown away. The villa is gorgeous and the staff is incredible. The head of house, Sean, takes care of all your vacation needs; and Chef Todd prepares the most delicious meals. Gina, the housekeeper, whips up a Bloody Mary that is legendary. We only left the villa twice…to golf and to check out the resort at Round Hill. We like to say that West Virginia is “Almost Heaven.” But Tradewinds IS heaven!
Stayed 7 nights in Jun 2023

10/10 Excellent

Susan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.”
Stayed 6 nights in Mar 2023

10/10 Excellent

Vickie M., US

Liked: Cleanliness, check-in, communication, location, listing accuracy
50th birthday couples celebration
We were more then pleased with our stay at Tradewinds …the staff is amazing . Sean, our butler went above and beyond to make sure we were relaxed and had everything we needed . I’m still dreaming about the jerk chicken and Rasta pasta that chef made . Every meal was so delicious. I don’t think I’ll ever book a hotel again ! This is the way to go . A true vacation where all your worries are taken care of for you so you can truly relax . We will be back !
Stayed 5 nights in Jun 2022

10/10 Excellent

Gretchen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Yeah mon!
We had an amazing stay at Tradewinds - total relaxation in a beautiful home, right on the ocean with private beach, with outstanding staff supporting our trip throughout. Terri is an incredible host, and is always extremely responsive. Sean took care of everything we needed whenever. Gina kept the home looking gorgeous at all times. And Derval, made spectacular gourmet meals through the day - lobster thermidor, filet mignon, Jamaican jerk chicken - and made sure we had the best desserts (chocolate soufflé, bananas foster 😋). For getaways we went for massages and lunch at Round Hill, and ziplining in Montpelier. My kids spent a ton of time in the pool, at the beach, and paddle boarding. One night we went to the Reggae night party up at the Club….so much fun! So if you are considering Jamaica and Tradewinds I say, yeah mon!
Stayed 7 nights in May 2023

10/10 Excellent

Samantha L., New York, New York

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 5 nights in Nov 2023

10/10 Excellent

Suzanne L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Slice of heaven Jamaica
We felt like we had arrived “home” as soon as we got off the bus! I refuse to call the people who cared for us staff, they were more like gracious friends. Our stay was fantastic, the food was divine, the house out of this world, and we had a time that will never be equaled. Thank you Terri for sharing your slice of heaven with us!!!!
Stayed 7 nights in Aug 2022

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spectacular
This lovely home right on the water was perfect for four couples with each room having a private bath and very comfy king beds. The staff made the week easy, happy, and yummy. Walking distance to the golf course and the beach club, although the house has a small private beach from which you can swim or snorkel. Tennis and other facilities at the club are easily accessible by the house’s golf carts.
Stayed 7 nights in May 2022

10/10 Excellent

stacy g.

Liked: Cleanliness, communication, location, listing accuracy
Great Girls Trip!
We had a great girls trip and thoroughly enjoyed staying at this beautiful property!! The communication with the owner was great and the team of staff members was such a treat!
Stayed 4 nights in Apr 2022

10/10 Excellent

Brad P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
First Class Experience at Tradewinds on the Sea!
Our 5-night stay at Tradewinds on the Sea at The Tryall Club was perfect in every way. I honestly can’t think of one thing that didn’t exceed expectations starting from the initial reservation process to the pre-trip communication with the owner to our first steps on property to the final check out. It was all first class. The villa felt like it was enveloped by the Caribbean Sea. It was spacious, comfortable (with seating and lounging options around every corner), private and very clean. We loved the open air vibe that Tradewinds was all about and the views were spectacular. The location was so convenient - steps from the water and a hop, skip and jump to the golf course and Beach Club. The bedrooms and bathrooms were nicely appointed and roomy. Throw in Tradewinds amazing pool, hot tub and small private beach and you have all you need for the vacation of a lifetime. While Tradewinds has it all for sure, but what makes the experience so unique and special was the attentive villa staff who made our vacation feel effortless. The staff were always looking out for us and responded to every request with a smile and “Ya Mon” - they also did an amazing job of anticipating our every need. Chef’s food was absolutely delicious. Every member of the house staff was so friendly and very professional. Tradewinds gets our highest rating and recommendation and we can’t wait until we can come back again.
Stayed 5 nights in Apr 2022

10/10 Excellent

Kristen W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Spring Break!
There was no reason to leave Tradewinds during our entire stay! The pool and accommodations were just as described. But what really made the home so special was the staff! The homeowner was a pleasure and a breeze to work with and we would love to come back one day! Thank you to all for a great week!
Stayed 6 nights in Mar 2022

10/10 Excellent

Kris W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Came as a guest and left as family.
Aside from the beautiful location, what has made our stay most memorable is the Villa Staff! As a very low-key family, each staff member was able to accommodate our personalities which provided us a very peaceful vacation. As I reflect on what it takes to truly operate the villa and provide a wonderful experience I am in awe at how everything was masterfully done in the background without us noticing most times. Chef David created culinary masterpieces, Sean offered suggestions that we hadn’t thought about, Gina was magical at swooping in and transforming bedrooms and living spaces, Jennifer was a doll who made sure our clothes and especially my tennis outfit were cleaned daily (I packed for only one lesson but ended up booking several lessons after discovering my new love), and Clavion and Peter made sure the grounds were beautiful. We feel rejuvenated and are looking forward to coming back next year. Take care everyone, The K Webb Family
Stayed 7 nights in Nov 2021

10/10 Excellent

Scott S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Celebration with friends
We had a wonderful stay at Tradewinds! I can’t say enough about our stay! Staff was a 10! The house was a 10! The airport arrival/ departure (ask for Denise) was a 10! This was true luxury all the way around! Amazing food, amazing sleep, amazing service! We will certainly be back!
Stayed 7 nights in Nov 2021

10/10 Excellent

Abigail H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tradewinds - Exceptional property, exceptional staff.
We are one day away from leaving Tradewinds by the Sea at the Tryall Club. Without a doubt, the best time we could have asked for. The villa was well-appointed, with all the amenities one would need for an amazing vacation. The villa owner was quick to reply in the months and weeks leading up to our trip, and checked in with us on the day of our arrival. Traveling during a global pandemic was nerve racking, however, she reassured us. What makes Tradewinds a truly exceptional place is the warm, genuine staff that go above and beyond to make sure you have everything you need for a relaxing holiday. Sean, Chef David, Gina, Clavion, and Jennifer are the best, and we are so grateful for their attention to detail and professionalism during our stay. The food, made by Chef David continued to “wow” us every night- and Sean attended to the details, so thoughtfully and so genuine. Gina and Jennifer took care of cleaning, laundry, and warm smiles daily. Clavion and Peter kept the grounds tidy. The team is truly top-notch. We look forward to seeing everyone again next year..
Stayed 7 nights in Sep 2021

10/10 Excellent

morgan l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jamaica Paradise
We had the pleasure of staying at Tradewinds this July. It was the most amazing property and the staff was top notch. Guests of all ages can enjoy all the amenities the vacation rental has to offer. Sean, David and Gina went out of their way to make sure we were taken care of. We spent most of our time pool-side enjoying the ocean view and watching the pelicans dive for food. The property is super clean and the beds were very comfortable. We were so sad to leave but left well rested and with a few extra pounds (Chef David is an amazing culinary artist). We will definitely book this vacation rental again!
Stayed 6 nights in Jul 2021

10/10 Excellent

Terry T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tradewinds - Perfection!
My family of 6 just returned from Tradewinds, which was by far, the best vacation we’ve ever taken. Sure, leaving the frigid North East US for Jamaica was awesome, the Tradewinds property and staff is what really made the trip special. A few highlights: 1) Even before leaving for Jamaica, dealing with Teri (the owner) was an absolute joy. She couldn’t have been more friendly and helpful and spelled out everything from A to Z. I was fully prepared for the visit, as she left no stone unturned. 2) The house was flawless from top to bottom. The furniture, bedding, TV’s, etc. were all top notch, and you could tell that Terri didn’t spare any expense with furnishing the property. Even the golf carts were very well kept, and fully charged daily. 3) The staff was equally flawless. Spearheaded by Sean (Head of House) the staff was friendly, and really made us feel at home. They were all great to our kids, and were very flexible with our schedule, as we were visiting Tryall with 5 other families, so we were all over the place. David (Chef) was excellent, and had great meals from breakfast to dinner. The rest of the staff, again, was incredible, laundry done every day, grounds were always well kept, and pool always clean. 4) Outside of the house, the staff and grounds at Tryall were great. Everyone was always kind and helpful, and the grounds were spotless. In summary, as you could probably tell, I would recommend Tradewinds to anyone and everyone. We intend to revisit Tradewinds for years to come, and congratulate Terri for doing such a great job with the house and putting together such a remarkable staff.
Stayed 7 nights in Mar 2021

10/10 Excellent

Kate K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise!!
We just returned from what will now be know as our best family vacation. Everything was perfect! We had high expectations because reviews were so good but the house and staff exceeded our expectations. We will be back next year!
Stayed 7 nights in Mar 2021

10/10 Excellent

Brett B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
More than a wow factor property - an amazing experience
Like many people, I spend way too much time researching destinations and selecting properties. I rarely write my own reviews, but I need to make an exception in this case. Tradewinds is a mind blowing property – set on it’s own private beach, with a view to Montego Bay sparkling in the far distance. Such a calming retreat, with cabanas to nestle into, a hot tub/spa that falls into a large infinity edge pool to swim and splash hat looks over the ocean beyond. Each room is it’s own private retreat, with luxurious ensuites, indoor/outdoor showers, and shutters that open to the waves and ocean breezes. The entire home has an indoor/outdoor feel and an authentic Caribbean vibe. Imagine massages in the open main room, high end TV screens even allowed for family movie night, with Pina Coladas and a warm breeze, incredible. We also loved Tryall. The course is fantastic, with signature holes through sugar mills and aqueducts. Family adventures using the provided carts to explore the property and see some of the amazing homes and views were a blast. The new beach pool is huge, with beach bar and restaurant, events, craft vendors, and a great house with a grocery store, boutique, and another infinity pool, this one with a swim up bar looking out over all of Jamaica beyond. But what makes Tradewinds so special is the amazing family you will have around you. From the gardeners, who showed us the flora and taught us to play croquet on the expansive grounds, our housekeepers, whose turndown service always included flowers and fresh linens, and David, an internationally practiced chef. We’ve had the chance to dine at some incredible venues around the world, and David’s talent and passion for cooking will not disappoint - fresh seafood, authentic sauces, and incredible soups and desserts. Finally Sean, who was more than head of house, he is a great person and he was able to make sure we felt comfortable and at home. He set up masseuses to come in, golf tee times, beach days in Negril, an excursion/waterfall hike in the mountains. Terri is a fabulous host. Excellent communication, and a commitment to making sure it’s a great experience from the moment you book. Tradewinds, and Tryall, is far and away the way to experience Jamaica. This is a must see venue, and a must meet staff. It is worth building your dates around the availability of this property and this caring group of people.
Stayed 6 nights in Feb 2020

10/10 Excellent

Alex S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Our stay at Tradewinds was 9 days and it was a great experience. The villa staff were absolutely terrific. The villa itself was perfect, it has a great location and everything in the villa is in excellent condition. The villa owner was outstanding with terrific communication. Everything that is advertised is 100% accurate. The only negative (which had nothing to do with the villa or staff) was the checkout process with the Tryall Club. The front desk clerk was both unprofessional and rude. It was only a minor glitch in an otherwise perfect stay.
Stayed 9 nights in Feb 2020

10/10 Excellent

Holli C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tradewinds
Everything was nothing short of AMAZING! The Tradewinds team , Sean , Gina & Chef David were EXCELLENT from start to finish! I couldn’t have celebrated my 50th birthday any better way than with my family at the Tradewinds . The pictures absolutely do it no justice ! You will be wowed from the panoramic rooms and soothed by the waves while swinging in the hammock! I still hear the waves ! The only sad part was leaving ! I could go on and on but I’d run out of space ! Thanks Terri for sharing this diamond in the rough ! And for being readily available when needed but yet providing space and freedom! As well as making sure Chef David had all he needed to create me a magnificent delisciuos birthday cake . And alll the special birthday surprises from the table setting with my name spelled out with flowers to my birthday bows on my chair for breakfast & dinner, to the birthday flowers on the bed (thanks to Gina) and what was extra is how the staff all came together to assist setting up a beautiful area with flower petals and roses for our sons surprise marriage proposal! (She said Yes!) It felt like our very own home the past few days ! And we absolutely cannot wait to return !! Beautiful experience & beautiful memories not soon forgotten! The Cameron Family
Stayed 5 nights in Jun 2019

10/10 Excellent

Mary Ellen H.

Beautiful property from top to bottom
Our visit at Tradewinds was, quite simply, the best. The property is everything described and more. The staff met our car on arrival with mojitos and cold towels and maintained that level of service our entire stay. This was truly a vacation where every request was met and accomplished by this remarkable staff. Sean was available ALL the time and drove us wherever we asked. We went out for lunch and dinner and truly felt we had our best meals prepared by David in this beautiful home. Next time, we won't leave at all. Tryall Club is beautifully maintained and our access to all the Club's facilities was seamless. Most of all we enjoyed spending our time in this fabulous home which is so tastefully decorated and impeccably maintained. The sound system is top of the line and everywhere. They have truly thought of everything to guarantee a memorable stay. The owner was very responsive, easy to work with, and all her suggestions were spot on. We are already planning our next stay.
Stayed 4 nights in Dec 2018

10/10 Excellent

Cie-jai B.

Fantastic Relaxing Family Vacation
Our stay at Tradewinds at The Tryall Club couldn't have been better. With three children ages six and under, the living space and the attentive staff exceeded our expectations. The owners have done an impeccable job with the interior design and upkeep of the villa. Each of the staff members was warm and friendly, and extremely professional. Chef David was a super star whose menu left us perpetually satisfied, yet wanting more. The staff truly worked well as a team and made our stay incredibly relaxing. The owner is very gracious and easy to work with as well. The resort itself is beautiful and has a solid offering of activities, including the beach bbq party with live reggae music. We had an amazing time and have been raving about to to all of our friends. Kudos to the owner and staff at Tradewinds. We hope to see you soon!
Stayed 6 nights in Dec 2018

10/10 Excellent

Tom M., Orlando Florida

Everything described and more......
My wife and I had a very relaxing time at Tradewinds. The staff were fantastic and accommodating - Sean, David & Gena. Chief David made some great meals 3 times a day of anything we wanted and welcomed new ideas. Sean was always around if you needed anything. Rooms were always clean and tidy., Tradewinds is new and clean inside and out, pool and outside areas are fantastic, great Sonos sound system and more large TV's then you can watch. Located just feet from the ocean where the waves put you to sleep every night. Tryall Club is a unique property. Terri the owner was also very helpful in pre-planning. We would recommend this home to anyone looking for a laid back vacation.
Stayed 3 nights in Nov 2018