Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House

Pineapple House

Montego Bay , Tryall  Jamaica
5
5
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Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
Pineapple House
From $3,071 USD - $5,714 USD / nt

From $3,071 USD - $5,714 USD / nt

Plan Your Trip

HAVE QUESTIONS?

USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK /INTERNATIONAL: +44 1978 368531
From $3,071 USD - $5,714 USD / nt
We love this villa because...
We love Pineapple House for its breathtaking 180-degree Caribbean Sea views, elegant indoor-outdoor living spaces, and exceptional five-star personalized service that makes every stay unforgettable.

Pineapple House – Luxury Jamaica Villa Rental at Tryall Club

A Caribbean Villa with Stunning Ocean Views

Pineapple House is the ultimate escape for guests seeking Jamaica villa rentals that combine elegance, comfort, and breathtaking scenery. Perched on Copperwood Ridge within the prestigious Tryall Club, this villa enjoys panoramic 180-degree views of the Caribbean Sea and offers easy access to world-class amenities including the Great House, championship golf course, tennis courts, spa, gym, and beach.

Classic Caribbean Elegance Meets Modern Luxury

Designed by renowned architect Oliver Messel, Pineapple House showcases timeless architecture blended with modern comforts. This five-bedroom villa offers the perfect setting for families, groups of friends, or those seeking luxury villas in Jamaica.

Villa Features

  • 5 bedrooms accommodating up to 10 guests.

    • 4 spacious master suites with king beds.

    • 1 bedroom with convertible twin beds.

    • Handicap-accessible suite on the lower level.

  • En-suite bathrooms in every room.

  • Private balconies and terraces with sea views.

  • Smart TVs with internet access.

  • Elegant Saltillo terracotta floors and custom cabinetry.

Outdoor Living in Paradise

The villa’s expansive 2,500 sq. ft. terrace is designed for seamless indoor-outdoor living. Relax or entertain in style with:

  • Heated infinity pool overlooking the Caribbean Sea.

  • Lush English garden with waterfall and gazebo.

  • Outdoor bar for sunset cocktails.

  • Spacious dining and lounging areas.

Personalized Service with Five-Star Staff

Your stay at Pineapple House comes with a dedicated household team to ensure a luxurious and stress-free holiday. Staff includes:

  • Private chef, trained at the Culinary Institute of America.

  • Butler and housekeeper.

  • Laundress and gardener.

Guests especially love Chef Rannoy’s signature Pineapple Painkiller cocktail, a house specialty.

Why Choose Pineapple House

  • Exclusive location within the Tryall Club Jamaica.

  • Ideal for Jamaica luxury villa rentals and family vacations.

  • Access to club amenities: golf, tennis, spa, gym, beach, and dining.

  • Perfect for groups, weddings, or special celebrations.

Quick Facts

  • 5 Bedrooms | 10 Guests | 5 Staff Members.

  • Hillside Location with Ocean Views.

  • Luxury Villa with Pool and Gardens.

  • Available for private villa rentals in Jamaica year-round.

If you are interested in renting this villa in Jamacia contact us today

Explore More Villas in Jamaica

USA/ Canada:  +1 347 707 1195

UK / International : +44 1978 368531

Email: [email protected]

For luxury villas to rent in other areas of the Caribbean  visit: www.worldwidedreamvillas.com

Amenities

  • Air Conditioned bedrooms
  • Air Conditioning
  • Beach Club Facility
  • Childrens Activities
  • Communal Facilities
  • Golf Cart
  • Golf Resort
  • Gym/Fitness Room
  • Office
  • Outdoor Jacuzzi
  • Private Garden
  • Private Pool
  • Restaurant
  • Shop
  • Sound System
  • Spa
  • Tennis Court
  • TV
  • WaterSports
  • Well Equipped Kitchen
  • Wireless Internet
See more details...
Bedroom : 5
Bathroom : 5

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • Laundress

Rate

FromToMin StayNightly RateWeekly Rate
18-Aug-202531-Oct-20257$3,071 USD$21,500 USD
01-Nov-202521-Nov-20257$3,221 USD$22,548 USD
22-Nov-202528-Nov-20257$3,571 USD$25,000 USD
29-Nov-202512-Dec-20257$3,221 USD$22,548 USD
13-Dec-202519-Dec-20255$5,714 USD$40,000 USD
20-Dec-202502-Jan-20267$5,714 USD$40,000 USD
04-Jan-202606-Mar-20267$3,697 USD$25,883 USD
07-Mar-202627-Mar-20267$3,697 USD$25,883 USD
28-Mar-202624-Apr-20267$3,697 USD$25,883 USD
25-Apr-202624-Jul-20267$3,382 USD$23,675 USD
25-Jul-202630-Oct-20267$3,225 USD$22,575 USD
31-Oct-202620-Nov-20267$3,382 USD$23,675 USD
21-Nov-202628-Nov-20267$3,571 USD$25,000 USD
28-Nov-202611-Dec-20267$3,382 USD$23,675 USD
12-Dec-202618-Dec-20267$3,382 USD$40,000 USD
19-Dec-202602-Jan-20277$3,382 USD$40,000 USD

Rental rates are subject to 10.00 % TAX plus 7.50 % service charge.

Location

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Get In Touch

CONTACT US

USA/CANADA: +1 347 707 1195
UK /International : +44 1978 368531
Barbados: +1 246-432-6307

Email : [email protected]

 

UK: 40 Knutsford Road, Alderley Edge, Cheshire SK9 7SF

Barbados: Indigo Courtyard, Holetown, Barbados Bb24917

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