• USA: +1 917 336 4477
  • UK: +44 744 147 3289

Similar properties

Pineapple House at Tryall- 5 bedrooms

What we like most
  • Incomparable ocean views
  • Stunning architecture and interiors
  • World-class hospitality from villa staff
Insider's Knowledge
  • Easy access to Tryall Club amenities
  • Spacious verandas and meandering terrace with heated pool
  • Certified chef from the Culinary Institute of America
Places close by
  • Tryall Golf Course & beach resort club (5 min golf cart ride)
  • Tennis courts, luxury spa, and Great House restaurant (short walk)
  • Watersports facility and beach grill (10 min golf cart ride)


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 Tryall 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

At The Tryall Club, the team is committed to continually improving their services and offerings to ensure that guests have the best possible experience during their stay. The Tryall Club is a private members club, so all guests 13 years of age and older are required to take out a Temporary Membership, which will be charged upon arrival at check-in.

Temporary Membership Dues now start at USD $32 per day, plus a 15% service charge, for guests ages 16 years and older who stay for one to four days. For guests who stay for five to seven days, the Temporary Membership Dues are now US $160 plus a 15% service charge. Children between the ages of 13 and 15 pay at a discounted rate of 50% plus a 15% service charge. For children 12 years and younger, Temporary Membership Dues are complimentary.

Includes beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, Reggae Nights & Beach Parties on selected nights.


Tryall Club


  • 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, 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 Pool, Helicopter Pad, Parking, Patio, Private Terrace, Restaurants nearby, Sea Views, Sun Loungers, Swimming pool
  • Services: Butler Included, Butler Service, Chef Included, Cleaning inclusive, Concierge Service, Daily maid service, Gardener, Kids club, Laundress, Linen provided, Maid service, Towels provided
  • Access: Off-road parking, Secure parking


Availability is on a request basis - please Enquire


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
- Nightly rate Weekly Min. Stay Change-over
Rate summary $ 2,857 - $ 5,714 $ 20,000 - $ 40,000 5 Nights -
Low Season 2024 20-Apr-2024 - 02-Aug-2024 $ 2,935 $ 20,548 5 Nights -
Low Season 2024 03-Aug-2024 - 01-Nov-2024 $ 2,857 $ 20,000 5 Nights -
Low Season 2024** 02-Nov-2024 - 13-Dec-2024 $ 2,935 $ 20,548 5 Nights -
High Season 2024 14-Dec-2024 - 20-Dec-2024 $ 5,714 $ 40,000 7 Nights -
Festive Season 2024 21-Dec-2024 - 03-Jan-2025 $ 5,714 $ 40,000 14 Nights -

Additional Information


Recommended staff gratuity at the end of your stay is 15% of the villa rental in low season and 10% in high season. Plan to pay your grocery and gratuity monies in cash: US dollars or Jamaican dollars.

**Thanksgiving may be charged at Premium rate.**


Listing not yet reviewed by any guest.
Special Offers
  • Get in Touch

    Ask us about our special offers

    Contact Us
  • Join Our Mailing List

    Get offers sent direct to your mailbox

    Receive Offers

Expert Reviews

Listing has not been reviewed by our experts

Inquire About Villa

  • Name is required.
    An email address is required.
  • A valid phone number is required.
  • We need travel dates
    We need travel dates
  • Tick the box to submit the form.
Alannah Harrington

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.

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