close ✕
pricipal Image

Pineapple House

The perfect Caribbean getaway, Pineapple House offers stunning ocean views, gorgeous architecture, and top-notch hospitality. The Tryall Club’s renowned golf course is visible from this magnificent home perched above Copperwood Ridge, which offers expansive 180-degree views of the Caribbean Sea. Guests enjoy easy access to the Great House, tennis courts, gym, spa, and beach, all just a short golf cart ride away.

Inspired by the renowned architect Oliver Messell, Pineapple House blends classic Caribbean elegance with modern luxury. The villa features five beautifully appointed bedrooms, including four master suites with king beds and a fifth bedroom with convertible twin beds. Each suite boasts custom cabinetry, Saltillo terracotta floors, en-suite bathrooms, and private balconies or decks with stunning views. A handicap-accessible master suite is conveniently located on the lower level. Smart TVs with internet access are installed in every suite.

The villa’s 2,500-square-foot terrace, which was designed for seamless indoor-outdoor living, provides plenty of space for dining, lounging, and taking in the scenery. The lush English garden with a waterfall, gazebo, outdoor bar, and heated infinity pool make this the ideal place to unwind or host guests.

An outstanding team is available to attend to all of your needs, including a private chef, butler, housekeeper, laundress, and gardener. Savor the delicious dishes prepared by Chef Rannoy, whose skills were refined at the Culinary Institute of America. Remember to enjoy the house speciality, the Pineapple Painkiller cocktail!

A stay at Pineapple House is pure paradise; you won’t want to leave!

 

REQUEST NOW VIEW GALLERY

AMENITIES AND SERVICES

Ac

Private terrace

Fully equipped kitchen

Wifi

Flatscreen tv

Sound system

Private swimming pool

Hot tub jacuzzi

Golf carts

Designated space for work

Complimentary international calls

  • Housekeeper
  • Laundress
  • Gardener
  • Chef
  • Butler

Tips can be paid in cash to the villa manager upon departure to distribute amongst the villa team, or you may place the amount on your Front Office account. When charged to your account this attracts a 3.5% surcharge charge.

A short golf cart ride or walk to The Great House restaurant, gym, reception, commissary, games room, library, tennis courts, pickleball, kids club, and nanny service, and the environment office. A short golf cart ride to the luxury spa, beach, beach club, watersports facility, beach grill, championship golf course, commissary, and tour attractions desk.

...

Bedroom 1:

  • King

Bedroom 2:

  • King

Bedroom 3:

  • King

Bedroom 4:

  • King

Bedroom 5:

  • King or Twin

WEEKLY RATES

Date
5 BED
Jan 3rd –Mar 6th   
$ 25,883
Mar 7th–Mar 27th   
$ 25,883
Mar 28th –Apr 24th
$ 25,883
Apr 25th–Jul 24th 
$ 23,675
Jul 25th–Oct 30th  
$ 22,575
Oct 31st–Nov 20th 
$ 23,675
Nov 21st–Nov 28th
$ 25,000
Nov 29th–Dec 11th 
$ 23,675
Dec 12th–Dec 18th 
$ 40,000
Dec 19th–Jan 3rd 
$ 40,000
Date
5 BED
Jan 3rd–Feb 12th
$ 31,900
Feb 13th–Feb 19th
$ 31,900
Feb 20th–Mar 5th
$ 31,900
Mar 6th–Apr 2nd
$ 35,850
Apr 3rd–Apr 23rd
$ 28,750
Apr 24th–Jul 23rd
$ 26,050
Jul 24th–Oct 29th
$ 24,850
Oct 30th–Nov 19th
$ 26,050
Nov 20th–Nov 26th
$ 35,850
Nov 27th–Dec 10th
$ 26,050
Dec 11th–Dec 17th
$ 44,000
Dec 18th–Dec 26th
$ 48,100
Dec 27th–Jan 2nd
$ 48,100

All villa rates are subject to a 7.5% (non-refundable) Administration Fee and a 10% Government Tax (increasing to 15% for stays from April 1st, 2027).

The Club requires all villa rental guests to have a temporary membership for their stay. Rates, inclusive of tax and service charge, are:

Adults (17 years and older): $45 per day

Teenagers (13 – 16 years): $25 per day

Children (12 and younger): Complimentary

REQUEST NOW

ADDITIONAL INFORMATION

  • Exclusions: Food and beverage costs are not included in the villa rate.
  • Shopping List: Guests will collaborate with their villa team to prepare a shopping list before arrival or upon check-in.
  • Billing: All food and beverage charges will be added to your final bill.
  • Estimated Costs: As a guideline, please budget approximately US$75 per person per day for in-villa food.
  • Dining Options: Guests also have the option to dine at one of the resort’s restaurants.
  • Guest Charges Agreement Form (sent to you from Guest Services prior to arrival)
  • Completion Required: You must complete the Guest Charges Agreement Form, providing the names of all guests for whom you will be covering charges during your stay.
  • Credit Card Authorization: A physical copy of your credit card will be required upon check-in for a pre-authorization of US$150 per person per day.
  • Golf Cart Rental: If a golf cart is not included in your villa rate, it can be rented for US$45 per day, plus 30% taxes, totalling US$58.50 per day.
  • Highchairs, Cribs, and Rollaway Beds: These items can be rented for US$11 per day each.

If you need extra cash while on the property:

  • You can request a cash advance against your credit card at the Front Office.
  • Notice Required: A one-day advance notice is necessary, with a maximum advance of US$200 per couple per day.
  • A 7.5% surcharge will apply.

Cost (round trip):
US$120 for 1–4 persons
US$30 for each additional adult (12 years and over)
US$16 for children aged 4–11
Children 3 years and under travel free

Additional Charges:
If you request a stop to shop, an additional fee of US$35 will apply.
Car and booster seats are available for rental at US$30 round trip.
A 3.5% surcharge applies if charged to your Front Desk account. However, you may pay your driver in cash to avoid this fee.

Rates:
Daytime (5:00 a.m. – 10:00 p.m.)
US$12.00 per hour for 1 child
US$15.00 per hour for 2 children

Nighttime (10:00 p.m. – 5:00 a.m.)
US$12.00 per hour for 1 child
US$15.00 per hour for 2 children

A minimum booking of 3 hours is required for nanny services. If care is needed for 3 or more children, an additional nanny is required.

If a nanny stays between 10:00 p.m. and 5:00 a.m., an additional US$50 per night will apply.

Nannies must be compensated for transportation: US$10 after 10:00 p.m., US$20 after midnight.

After 10:00 p.m., nannies must be paid for at least 3 hours, even if they work fewer hours.

Rates for nanny services are doubled on public holidays.

A 3.5% surcharge applies if charged to your Front Desk account.

YOU MAY ALSO LIKE

Deluxe

Avalon

  • 4 bedrooms
  • 8 guests
  • 3 Household staff

If you are looking for privacy, tranquility, a view of the sea and gorgeous gardens then look no further. This very special home has enchanted many not just for its warmth and comfort but for the caring team of staff that work here.

View Villa From $1,360 /per night

Deluxe

Bali Hai

  • 5 bedrooms
  • 10 guests
  • 7 Household staff

Quiet, serene and set on a hill with far-reaching ocean views surrounded by a truly remarkable garden, Bali Hai is loved by its guests as it allows them to relax, reflect, rejuvenate and recharge. A masterful bringing together of the artistic beauty of Bali with a spirited sense of fun that is uniquely Jamaican. Bali Hai is nothing short of unique. The home has evolved after the owner’s many trips to the East over countless years.

View Villa From $1,786 /per night

Luxury

Bella Vista

  • 5 bedrooms
  • 10 guests
  • 8 Household staff

Bella Vista villa is a Jamaican celebration. Architecturally designed and built by Jamaicans…for its Jamaican owner, it opens up with the reminiscent grandeur and elegance of a Jamaican Great House with the comfort and warm hospitality of the people of the island. Conspicuously perched upon five (5) acres of beautifully landscaped grounds, details considering its environment were not spared and so, it is the tropical sunlight that powers the energy efficient led lighting, hot water, and saltwater pools.

View Villa From $2,678 /per night

Classic

Bluebird

  • 4 bedrooms
  • 8 guests
  • 5 Household staff

Surrounded by a lovely garden and with a super view of the cobalt ocean, Blue Bird is a Tryall classic offering spacious airy accommodation that epitomizes living in the tropics.

View Villa From $819 /per night

Luxury

Bougainvillea House

  • 5 bedrooms
  • 10 guests
  • 5 Household staff

Stunning architecture, tranquillity, glorious sea views, beautiful gardens and an emphasis on stylish comfort are all hallmarks of this superb luxury villa.

View Villa From $2,500 /per night