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Pineapple House at Tryall- 5 bedrooms


Welcome to Pineapple House at the Tryall Club, a 5 bedroom private villa that combines luxury and comfort in all the right ways. This Jamaican villa has recently undergone a complete renovation and been transformed into a distinctive architectural masterpiece.

Luxury living is all about the details, and Pineapple House does just this and more. Distinctive in its architecture, Pineapple House’s extensive fret-work and ‘Oliver Messel’ design is defined by its Messel-green shutters, coral stone exterior and overall rustic elegance.

Pineapple House is perched on a stunning part of the Tryall Club overlooking the 18-hole world-famous golf course with panoramic views of the Caribbean Sea. While you have the privacy of your own luxury villa, you will be within walking distance to Tryalls Great House, gym and tennis courts, massage centre and a short golf cart ride to the Golf course and beach.

The villa has recently undergone a complete renovation and been transformed into a distinctive architectural masterpiece. The villa boasts unique architecture with its extensive fret-work and ‘Oliver Messel’ design defined with Messel-green shutters, coral stone exterior and rustic elegance.

The interior design combines sophistication and art with its rich mahogany furnishings and bright colours. Pineapple House boasts four master bedrooms fitted with King or queen-sized beds and one bedroom fitted with twin beds which convert to a king. The master suites are equal in size, and each has a lavish en-suite bathroom. The lower level master bedroom is handicap-accessible. Smart televisions with internet capability are installed in each suite. All bedrooms have their own private balcony or deck with breathtaking views.
Pineapple House is famous for its views. The 2,500 square feet meandering terrace on the main level overlooking the diving heated pool, the Gazebo, covered outdoor dining area, lounging areas and bar all take full advantage of them. There is plenty of space to entertain all tastes with its well-manicured lawns which are great spots for the children to play, the English garden with its waterfall is the loveliest place to sit and read or enjoy a cocktail!

Check out all that the Tyrall Resort Jamaica has to offer its guests.

Staff When you stay at Pineapple House, you will be personally cared for by your own wonderful Butler, Chef, Housekeeper, Laundress and Gardener all of whom will cater to your every need...and they never run short of their popular speciality drink, “Pineapple Painkiller”... You will want to stay here forever!

AC bedrooms
Heated swimming pool
3 carts
2 king/2 queen/1 twins (joinable)
Free Wireless internet
Smart TVs
Cable television
Children Welcome
Indoor/Outdoor Dining
I-pod docks
Blow dryers
Flat-screen TV
En-suite bathroom
Private balconies
Free on-property shuttle service

a short golf cart ride to golf, beach, Walking distance to tennis, massage centre, fitness centre, boutique, Tryall market, games room, Kid's Club

The Tryall Club requires all villa and condo guests to become members during their stay via a temporary membership fee of US$130 (plus 15% service charge) per week for each guest 16 or older, or US$26 (plus 15% service charge) per day per person for stays of less than 7 days.


Montego Bay

Accommodation, Facilities and Services

  • Bedroom(s): 5 ( Sleeps 10 )
    5 Double with en-suite
  • Bathroom(s): 5
    5 Showers, 5 Wash basins, 5 Toilets
  • General facilities: Balcony / Deck, Bar, Ceiling Fans, Computer, Garden, Garden View, Gated Entrance, High Speed Internet, Ice Maker, Panoramic Views, Parking, Pool, Private Location, Private Terrace, Safe, Security, Terrace, Wifi
  • Indoor facilities: Air conditioning, All Bedrooms Air Conditioned, All Bedrooms En Suite, Blender, CD Player, Coffee Maker, Drier, DVD Player, Freezer, iPOD Docking Station, Iron and Board, Luxury Finishes, Microwave, Phone, Safe, TV
  • Outdoor facilities: Beach Access, Golf Views, Heated Swimming Pool, Helicopter Pad, Parking, Patio, Private Terrace, Restaurants nearby, Sea Views, Sun Loungers, Swimming pool
  • Services: Butler Service, Cleaning inclusive, Concierge Service, Daily maid service, Gardener, Kids club, Laundress, Linen provided, Maid service, Personal Butler Included, Personal Chef Included, Towels provided
  • Access: Wheelchair access, Off-road parking, Secure parking


  • Local activities: Climbing, Cycling, Fine Dining, Fishing, Golf, Hiking, Horse riding, Shopping, Swimming, Tennis, Walking, Water Sports


Availability is on a request basis - please Enquire


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
02-Jan-2021 - 09-Apr-2021
Nightly rate Weekly Min. Stay Change-over
$ 2,571 $ 18,000 7 Nights -
18-Apr-2021 - 18-Dec-2021
Nightly rate Weekly Min. Stay Change-over
$ 1,929 $ 13,500 5 Nights -
19-Dec-2021 - 01-Jan-2022
Nightly rate Weekly Min. Stay Change-over
$ 4,286 $ 30,000 14 Nights -
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 1,929 - $ 4,286 $ 13,500 - $ 30,000 5 Nights -
02-Jan-2021 - 09-Apr-2021 High Season 2021 $ 2,571 $ 18,000 7 Nights -
18-Apr-2021 - 18-Dec-2021 Summer 2021 $ 1,929 $ 13,500 5 Nights -
19-Dec-2021 - 01-Jan-2022 Christmas/New Year 2022 $ 4,286 $ 30,000 14 Nights -

All prices are subject to VAT at 15%


Taxes & Fees of 15% must be applied to the villa rental rate (Government Consumption Tax of 10% + Tryall Club Administration Fee of 5%)


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Our team know each destination and every villa we feature.

We also offer a personalized and fully complimentary concierge service so every part of your trip will be taken care of ensuring you have a hassle free vacation.

We look forward to hearing from you.

Sean Walsh

jamaica Specialist

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    • Type: Villa
    • Sleeps: 10
    • Bedroom(s): 5
    • Bathroom(s): 5
    • Board: Catered
    • Long term rentals: No
    • Pets: No
    • Children: Yes, great for kids
    • Wheelchair: Yes
    • Eldery or infirm: Yes
    • Holiday type: Family, Honeymoon, Resort, Sea Views, Walk to Beach