Hanover Windward Garden Villa at the Tryall Club

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Sleeps: 8 - 12 Bedrooms: 6 Bathrooms: 8


10% discount!
Pool Modern Beach Nearby Ideal for Kids All Bedrooms En-Suite Wheelchair Access


Hanover Windward Garden Villa at the Tryall Club is a majestic home offering classical colonial elegance, peerless comfort and world-class amenities, perched overlooking the glistening Caribbean Sea.

This sumptuous home’s exterior showcases the best of quintessential plantation style architecture: formally symmetrical lay out and sleek marble pillars with long balconies and balustrades, along with the hallmark cedar roofs and jalousie windows.

Set overlooking the glistening pool and sparkling seas, there is a natural interplay between indoor and outdoor living, and when lit up at night, the house and pool are a dazzling sight. Outdoor living is executed stylishly, with an array of outdoor lounge spaces, a pool-side bar and abundant dining spots from family meals to intimate moments on the balconies, with the characteristic use of natural timber and wicker alongside vibrant aqua and cobalt blue fabrics for that breezy sea-side feel.

Hanover Windward Garden Villa is a great party house, with a five speaker sound system in both the house and the pool bar, ideal for rocking pool parties with the rum cocktails flowing. Executed with indulgence in mind, this unapologetically opulent home panders to guests’ every whim, from delectable chef-prepared meals to pool-side lounging to popping into the golf buggy down to the club.

The interiors are vivacious and airy, offering an abundance of designer flair, blending both European finesse and Caribbean ease. With glittering chandeliers, contemporary art, and chic, polished mahogany furnishings along with art-nouveau inspired fabrics and cool marble flooring.

Hanover Windward Garden Villa offers six bedrooms with six en-suite bathrooms (the beds can be arranged as king sized beds, or as two kings with eight twins). All bedrooms have HD cable television, remote control air conditioning, safes, ceiling fans and glorious Travertine marble en-suite bathrooms. Four bedrooms open to private furnished balconies and lovely sea views from both bedroom and bathroom.  Two bedrooms downstairs open to furnished terraces, gardens and soft lawn.

With a pool table, football goals, an array of entertainment options and full staff offering, guests will barely need to leave the comfort and gracious confines of this impressive abode.

Montego Bay glitters at night across the water, whilst at every turn guests can absorb the changing colours of the Caribbean Sea. Windward offers the last word in luxury, no detail is left under thought, whilst guests can enjoy that low-key and understated feel of having their own pad and privacy in combination with world-class resort standards.

Oliver Approved

What you should know…

  • Remember, it is customary to pay a 15% Gratuity fee before leaving your Villa in Jamaica
  • The pool is unfenced (toddlers will need to be monitored)
  • Two of the bedrooms are on the ground floor, the rest are on the first floor
  • The Tryall Club requires all villa and guests to become members during their stay via a Temporary Membership Fee

Property Features

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

The Villa

Hanover Windward Garden Villa...

Ground Floor
- King bedroom, with en-suite bathroom
- Twin bedroom, with en-suite bathroom
- Living area
- Fully equipped kitchen
- Utility room

First Floor
- Master bedroom, with en-suite bathroom & terrace access
- King bedroom, with Daybed, en-suite bathroom & terrace access
- King bedroom, en-suite bathroom & terrace access
- Twin bedroom, with en-suite bathroom & terrace access
- Dining area
- Living area

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


About the surrounding area of Hanover Windward Garden Villa at the Tryall Club
Beach Nearby <1hr to Airport Watersports Canoeing/Kayaking Golf Nearby Tennis Nearby Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages
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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 Sandy Bay


Nearest Restaurant Pachie's


Nearest Bar/Pub Glama Sports Bar


Nearest Beach Tryall Club

(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

Hanover Windward Garden Villa at the Tryall Club is an ideal choice for families, with an intentionally family-friendly floor plan consisting of three master bedrooms, each adjacent to a children’s bedroom, with a Kids Club and playground close by, this extremely secure, immaculately staffed home also has access to a kids club as well as a range of resort amenities.

The pool will offer hours of splashy fun, whilst older kids will have all their entertainment needs met with cable televisions and DVD players.

Just off the coast of Montego Bay is the marine park, which offers mile upon mile of luminous coral reefs and mangroves. For an action packed family-friendly day out, Walter Fletcher Beach has a go-kart track, tennis courts and an aquatic theme park

Jamaica offers endless, thrilling and memory-making outdoor pursuits for children, for older kids zip lining across the across the island's rainforests, or younger children will delight at aqua parks and shallow waters beach waters.

One of the picks of the northern coast would be close up dolphin encounters at Dolphin Cove in Ochos Rios, which is immensely popular due to its wide range of appeal to all ages. From feeding them to swimming with stingray, to glass bottom boat trips to shark shows and a nature trail, this is an ideal day out for the family.

The pick of the beaches for kids has to be Doctor’s Cave beach, it has a range of trampolines, including in-water trampolines for the older children, shallow waters full of colourful fishes and delicious chicken nuggets at the restaurant right on the beach.

Kids Activities Close-by

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

Onsite Facilities

  • Football net
  • Heated Pool
  • Outdoor Games
  • Table Tennis
  • Table Football
  • DVD

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 $2000 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? 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
- Bedrooms will be allocated dependent upon ‘Number of Guests’ at the time of Booking. Any unused Bedroom(s) may not be available to Guests.
- 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 10% Government General Consumption Tax + 7.5% Tryall Club Administration Fee

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - £12,128
Aug 3rd 2024 - Nov 2nd 2024 £8,411 £11,771
Nov 2nd 2024 - Dec 1st 2024 - £12,128
Dec 1st 2024 - Dec 14th 2024 - £12,128
Dec 14th 2024 - Nov 26th 2025 - £28,353

Prices based on an occupancy of 10 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - £14,029
Aug 3rd 2024 - Nov 2nd 2024 £9,112 £12,753
Nov 2nd 2024 - Dec 1st 2024 - £14,029
Dec 1st 2024 - Dec 14th 2024 - £14,029
Dec 14th 2024 - Nov 26th 2025 - £28,929

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - €13,245
Aug 3rd 2024 - Nov 2nd 2024 €9,185 €12,855
Nov 2nd 2024 - Dec 1st 2024 - €13,245
Dec 1st 2024 - Dec 14th 2024 - €13,245
Dec 14th 2024 - Nov 26th 2025 - €30,964

Prices based on an occupancy of 10 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - €15,321
Aug 3rd 2024 - Nov 2nd 2024 €9,951 €13,927
Nov 2nd 2024 - Dec 1st 2024 - €15,321
Dec 1st 2024 - Dec 14th 2024 - €15,321
Dec 14th 2024 - Nov 26th 2025 - €31,594

Prices based on an occupancy of 8 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - $14,375
Aug 3rd 2024 - Nov 2nd 2024 $9,969 $13,952
Nov 2nd 2024 - Dec 1st 2024 - $14,375
Dec 1st 2024 - Dec 14th 2024 - $14,375
Dec 14th 2024 - Nov 26th 2025 - $33,607

Prices based on an occupancy of 10 people:

Rental period 5 Nights Weekly
May 25th 2024 - Aug 3rd 2024 - $16,629
Aug 3rd 2024 - Nov 2nd 2024 $10,800 $15,116
Nov 2nd 2024 - Dec 1st 2024 - $16,629
Dec 1st 2024 - Dec 14th 2024 - $16,629
Dec 14th 2024 - Nov 26th 2025 - $34,290

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.


  • Exceptional

    on 01/12/2018

    The staff was professional, kind & fun! They made our stay at Tryall great fun! Thank you for making our stay exceptional.

  • Utterly great

    on 01/11/2018

    The staff are personable, professional & made our trip. The attention to details was amazing. They went above & beyond. We will return every year.

  • Extremely good

    on 01/10/2018

    Windward is amazing. The house is beautiful and the staff is great. Damion is charming and professional and made us feel at home immediately. And Chef Knight is very talented - the food has been fantastic. Just wanted to let you know how much we appreciate everything!

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