Tradewinds at the Tryall Club

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Sleeps: 8 Bedrooms: 4 Bathrooms: 4


10% discount!
Wow Factor
Modern Ideal for Kids Hot Tub Walk to Beach All Bedrooms En-Suite Wheelchair Access

Tradewinds is a modern family home in the beautiful city of Montego Bay. The luxurious waterfront villa boasts a massive garden full of towering palm trees and stone paths and is home to a private beach.

At Tradewinds you are truly surrounded by the best that nature has to offer with both lush greenery and the beach being your immediate environment. Not to mention the awe-inspiring views of the horizon and beyond!

The home’s living room incorporates high ceilings and neutral coloured walls that emphasize the ample living space available. The room’s light blue décor adds a calming and serene ambience which can be enjoyed while looking out onto the garden. Guests can also sink into the cosy sofas while unwinding and watching the television. Inside, guests will find a quaint little mini bar with a tantalising selection of exotic beverages and of course, the islands favourite liquor, rum! Pair that with the indoor sound system and you’ve got yourself a private party.

Beautiful white décor and walls are used throughout the villa, making it feel like an exclusive show home. Tradewinds also benefits from an open plan design which creates ample social space.

Outdoors, you can dine right by the ocean with an inviting dining area for eight situated in front of the sea. The dining table is brightly decorated with flowers and refined tableware. You’ll want to savour meals here, under the bright blue or starry night sky.
The villa comes equipped with two complimentary golf carts, a four-seater and a six-seater. These can be used to transport you around the Tryall Club. After all, who wants to walk in this blazing hot climate?

Oliver Approved

What you should know…

  • Remember, it is customary to pay a 15% Gratuity fee before leaving your Villa in Jamaica
  • When using the air-conditioning, please ensure to keep the doors and shutters firmly closed
  • The Tryall Club requires all villa guests to become members during their stay via a Temporary Membership Fee

Property Features

Private Pool Heated Pool Wi-Fi/Internet Air-Con Hot Tub BBQ Hairdryer All Bedrooms En-Suite Tennis Court Ground Floor Bed & Bath TV Wheelchair Access Outdoor Games Table Tennis DVD Ceiling Fans Beachfront

The Villa

Tradewinds is a simply stunning 4-bedroom villa within the Tryall Club. Being on-top of the beach, you and your guests have the luxury of taking to the waves or simply sloshing off in the Jacuzzi and private swimming pool.

Ground Floor
- Master bedroom, with en-suite bathroom
- Two King bedrooms, with en-suite bathrooms
- Communal bathroom
- Dining & living area
- Fully equipped kitchen
- Media room
- Utility room

- King bedroom, with en-suite bathroom

- Private swimming pool, with Roman steps access
- Jacuzzi
- Lawn area
- Outdoor dining & furniture
- Poolside shower
- Private Parking
- Sun loungers


About the surrounding area of Tradewinds at the Tryall Club
Walk to Beach Walk to Restaurant <1hr to Airport Watersports Canoeing/Kayaking Golf Nearby Tennis Nearby Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages Seafront
Loading map

Located on 200 acres of unspoiled Jamaican forest, the Tryall Club offers privacy, peace and tranquillity to its guests. A former plantation, the Tryall Club has since dedicated itself to the preservation of its natural landscape and is now home to over 30 species of non-fruiting trees, including rare grey birch trees, and 12 species of fruit trees.

On-site you’ll find a member’s only beach club for Tryall Club residents, boutique shops, tennis courts and one of Jamaica’s finest 18-hole golf courses. Food and drink is available at Tryall Club, with a beachside grill, two restaurants and two bars. There are 2 swimming pools, a zero-entry heated infinity-edge swimming pool directly above the beach and 2nd pool at the Great House with swim-up bar service available during the winter season.

Water sports facilities are located on the main beach where you can enjoy complimentary Kayak and paddleboards, rent hobie cats, book water skiing, banana boat rides and sailing lessons (all motorised water sports are charged locally).

There is a reef offshore that can be viewed from a glass bottom boat or snorkelers and divers can explore, bottom and deep-sea fishing trips can also be booked.

To help stay in shape while away the resort has an ocean facing gym. Qualified yoga instructors are available and there are 9 tennis courts along with tennis pros, hitting partners and ball boys.

If you want to go off-site, you’ll find the nearby area easy to navigate and easily accessible by local taxi services which can be arranged for you by the Tryall Club concierge team. In both Sandy Bay and Hopewell, you’ll find additional shopping and dining opportunities offering plenty of variety, from upscale beachfront cuisine to casual local hotspots.

Just 30 minuites drive away is Montego Bay, Jamaica's tourism capital and arguably one of the Caribbean’s premier resort destinations. It is the island's second city in terms of size and importance and has long been a playground for the world's rich and famous.

The City's streets are colourful and lively, with craft market stalls, shops and banks. You can visit the renowned white-sand Doctor's Cave Beach which has attracted celebrities and socialites from all over the world. Legend tells that the beach is fed by healing mineral springs, whether or not the legend is true, the beach certainly holds the most uncommonly clear and sparkling waters.

As well as dazzling waters, Montego bay also offers history, culture and wildlife. The Rocklands Feeding station is a must for bird lovers, located only minutes from Montego Bay. The Belvedere estate also draws in tourists from every area, one of the first sugar cane plantations in Jamaica and is still a working estate.

There are numerous spa's, restaurants, nightclubs, historic cites, watersports and adventure parks at your disposal as a vacationer at Montego Bay. The ideal holiday destination for families, couples and friends alike.

Read more about Jamaica

Local Amenities
Nearest Airport Sangster International Airport


Nearest Town/City Lucea


Nearest Restaurant Tryall Club

(Walking Distance)

Nearest Bar/Pub Tryall Club

(Walking Distance)

Nearest Beach Tryall Beach

(Walking Distance)

Nearest Golf Tryall Club

(Walking Distance)

Nearest Tennis Tryall Club

(Walking Distance)

About the Island & Getting There

About Jamaica

We have assembled a guide on some of our Jamaica highlights, so please check it out!

Prior to Booking

Please be aware that Jamaica is an island nation that experiences weather patterns dictated by the Atlantic Ocean to the north of the island and the Caribbean Sea to the south of the island. This tropical rainforest climate results in the island experiencing a hurricane season, which usually occurs between June to November. When thinking about booking your holiday to Jamaica, please consult Foreign travel advice for more information.

Entry Requirements

Tourists who are British Citizens will not require a visa upon arrival and Departure Tax is included in most flight costs. Please check Entry Requirements before departure.

Getting There

Jamaica has two international airports, Donald Sangster in Montego Bay and Norman Manley, Kingston.

From the US:
There are many direct flights with Jet Blue, Caribbean, Delta, American and United from cities including New York, Chicago, Miami, Atlanta, Charlotte, Dallas, Houston and Philadelphia.

From the UK:
There are direct flights to Montego Bay from Gatwick and Manchester with American Airlines, British Airways or Virgin Atlantic. Glasgow and Belfast passengers can also fly via the US with United Airlines.

A. Sangster International Airport, Montego Bay,
B. Norman Manley International Airport, Kingston, Kingston Parish:

View large map


Best Suited For: All Ages
Ideal for Kids Ideal for Teens Ideal for Xmas/NY

Kids will have tons of fun at one of Jamaica’s most exciting attractions, Kool Runnings Waterpark. The park is full of exhilarating water rides including 10 unique water slides and the chance to travel along the Rio Bueno Lazy River.

The park is full to the brim with activities and is home to water cannons, paintball, outdoor laser tag and go-karts. After all that activity, pop over to the Sweet Potato Grill for tasty jerk chicken and smoothies before settling down to watch what’s happening on the entertainment stage. Kool Runnings Waterpark is a 50-minute drive away from Tradewinds and is well worth the visit for a thrilling day out.

Hummingbird Kids Club is within walking distance and this superb service enables parents to have the little ones amused, especially if Mum & Dad want some one-on-one time with one another.

Kids Activities Close-by

  • Beach Nearby
  • Walk to Beach
  • Walk to Restaurant
  • <1hr to Airport
  • Watersports
  • Canoeing/Kayaking
  • Tennis Nearby
  • Horse Riding
  • Outdoor Pursuit & Activities
  • Tourist Towns & Villages

Onsite Facilities

  • Heated Pool
  • Tennis Court
  • Outdoor Games
  • Table Tennis
  • DVD
  • Beachfront

Services Available

  • Chef/Cook Included
  • Maid Service Included
  • Babysitting Available


Oliver's Extras

  • Pre-Stocked Fridge Available
  • Transfers Available
  • Chef/Cook Included
  • Maid Service Included
  • Babysitting Available
  • Butler Included
  • The Tryall Club temporary membership - Fees apply
  • 2 complimentary golf carts for transportation throughout the resort

At Oliver’s Travels we pride ourselves on going that little bit further for our guests. From private chefs to babysitters we can help you arrange those little extras that make it a truly memorable holiday. Simply fill in the concierge request form or contact the Oliver’s Concierge Team who will be happy to help. We can typically help you arrange any of the following:

- Maid service/extra cleaning
- Private chef/cook/catering
- Welcome hamper/pre-stocked fridge
- Local day-trips or tours
- Airport pick-up/drop-off
- Babysitting/childcare services

Villa Staff included at this property:
A full-time dedicated chef, butler, housekeeper and personal laundress attend exclusively to your villa.

Your cook will handle grocery shopping and meal preparation. They will pre-purchase your first few meals plus pantry staples, then finish the week's shopping after meeting with you. At week's end, they will present receipts for all food and beverage and reconcile your account. A typical grocery budget is $55-$65 per adult per day and $20-25 per day for preteens. This may vary up or down depending on market prices and menus.(more luxurious items such as shrimp, lobster, imported meats and Champagne will incur a further charge). 

Your cook will also pre-purchase a small starter bar (a few bottles of Red Stripe, moderately-priced wine and rum). Additional alcohol requests will increase your budget. If you wish to go to the various markets with them, you are welcome. Otherwise, simply review your tastes and distastes with them and they'll handle it all while you stay at the villa and relax.

A nanny can be arranged for an average of $12 per hour. Guests should plan to add approximately $20 per day for food for their nanny.

For any requests simply fill in the concierge request form or contact the Oliver’s Concierge Team.

Please note that all extras are subject to availability and must be requested in advance of the holiday (prices on request). Due to some rural/remote locations, not all services will be available at all properties. However, we will always do our best to fulfil your requests!

Terms & Conditions

These terms and conditions may be amended from time to time.

Security deposit A credit card will be collected and charged $1500 upon check-in at the Tryall Club. The amount will be refunded after check-out if there are no incidents/damage at the property.
Arrival time 3.00 p.m.
Departure time 11.00 a.m.
Energy costs included? Included in the rental price
Linen & towels included? Included in the rental price
End of stay cleaning included? Included in the rental price
Changeover day Saturday during Peak Season
Minimum stay 5 nights (Mid April - Mid December); 7 nights (Thanksgiving week and Mid December - Mid April);
Internet access? Wi-Fi connection included
Pets welcome? Pets are not allowed
Smoking Allowed? Smoking & Vaping is not permitted inside the villa
Insurance It is recommended that all guests take out insurance to cover against potential cancellation and any accidental damage caused during your stay at the property.
Damage Waiver Bookings to this property will incur a non-refundable 'Damage Waiver' of $149, to be paid by the guest.

Villa Conditions
- A obligatory Gratuity rate of 15% of the overall booking is due to be paid to the Staff before departure. Please plan to pay in Cash (US Dollars or the local currency).
- A 50% deposit may be required for bookings that include Thanksgiving, Christmas or New Years Eve.
- The Tryall Club requires all villa guests to become members during their stay via a Fee of US$160 (plus 15% service charge) per week for each guest 16 years and over, or US$32 (plus 15% service charge) per day per person for stays of less than 7 days. Payable Front Desk in the Great House when you register.

Rental Rates

Please note: All rates below are subject to 15% (10% Government General Consumption Tax + Administration Fee of 5%)

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 19th 2024 - Aug 3rd 2024 - £16,624
Aug 3rd 2024 - Nov 2nd 2024 £11,243 £15,736
Nov 2nd 2024 - Dec 1st 2024 - £16,624
Dec 1st 2024 - Dec 13th 2024 - £16,624
Dec 13th 2024 - Nov 20th 2025 - £33,440

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 19th 2024 - Aug 3rd 2024 - €18,058
Aug 3rd 2024 - Nov 2nd 2024 €12,214 €17,094
Nov 2nd 2024 - Dec 1st 2024 - €18,058
Dec 1st 2024 - Dec 13th 2024 - €18,058
Dec 13th 2024 - Nov 20th 2025 - €36,326

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 19th 2024 - Aug 3rd 2024 - $19,647
Aug 3rd 2024 - Nov 2nd 2024 $13,288 $18,597
Nov 2nd 2024 - Dec 1st 2024 - $19,647
Dec 1st 2024 - Dec 13th 2024 - $19,647
Dec 13th 2024 - Nov 20th 2025 - $39,521

Please note that these prices/rates are a guide only and may not be correct at the current date. For an accurate quote, please enquire.


  • Great Vacation

    on 11/05/2018

    We stayed at Tradewinds last May and has such a blast. Our kids loved the pool and the villa was just perfect for us. The staff are just so friendly, it made our stay extra special. I would highly recommend the villa and the resort.

  • Amazing!

    on 28/11/2016

    Amazing!!! House was a little dated but staff made up for it. Perfect weather too. All went perfectly. Thanks again!

  • Tradewinds

    on 10/06/2016

    Multigenerational family had the pleasure of visiting tradewinds. The property is beautiful, but it's the staff that made our trip. Gina, Tina, Clavion and chef Vincent are absolutely awesome. We had great service and they felt like family. The food was great. Clothes were washed and ironed daily. Miss Gina made the best rum punch. We also hasd a good experience going to the local grocery store with Vincent. One night we saw 3 crabs and got a fun lesson from Clavion- my 9 year old loved it.

    The complimentary glass bottom boat tour was a lot of fun. Disappointed the Beach BBQ night was cancelled though. No surprises with the costs. Using the golf carts to ride through the property was also awesome. Family age ranged from 9. year to 71 years and everyone had a blast. Will be back to tradewinds next year if the same staff is there.

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