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 Villa at Tryall Club, Jamaica

Your Perfect Jamaica Villa Retreat

Nestled on Copperwood Ridge within the renowned Tryall Club, Pineapple House is a stunning Jamaica luxury villa designed for travelers seeking elegance, comfort, and breathtaking sea views. Overlooking the Caribbean with sweeping 180-degree vistas, this five-bedroom private villa is only minutes by golf cart from the beach, Great House, championship golf course, tennis courts, gym, and spa.

Timeless Caribbean Style

Taking inspiration from the celebrated architect Oliver Messel, Pineapple House blends traditional Caribbean charm with refined modern living. Perfect for family villa holidays in Jamaica or group getaways, the home offers spacious interiors, stylish design, and every modern convenience.

Accommodation Highlights

  • 5 bedrooms (sleeps 10).

    • 4 master suites with king beds and en-suite bathrooms.

    • 1 bedroom with twin beds (convertible to king).

    • Handicap-accessible suite on the lower level.

  • Private balconies and terraces with ocean views.

  • Saltillo terracotta tiles and custom-designed cabinetry.

  • Smart TVs and Wi-Fi in each suite.

Outdoor Living at Its Best

The villa’s design embraces open-air Caribbean living, with a 2,500 sq. ft. terrace that connects seamlessly to the gardens and pool. Guests enjoy:

  • Heated infinity-edge pool overlooking the sea.

  • Tropical gardens with waterfall, gazebo, and shaded areas.

  • Alfresco dining and outdoor bar for entertaining.

  • Expansive lounging and sunbathing areas.

Five-Star Villa Staff

Pineapple House comes fully staffed to ensure an effortless stay. The villa team includes:

  • Private chef (Culinary Institute of America trained).

  • Butler, housekeeper, laundress, and gardener.

  • Personalized dining with both international and Jamaican flavors.

  • Signature cocktail: the refreshing Pineapple Painkiller.

Why Book Pineapple House?

  • Exclusive location at the prestigious Tryall Club Jamaica.

  • Luxury hillside villa with panoramic Caribbean views.

  • Full access to club facilities including golf, tennis, beach, spa, and dining.

  • Ideal for Jamaica villa rentals, private escapes, weddings, or family gatherings.

  • A perfect balance of Caribbean elegance and modern luxury.

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

From To Min Stay Nightly Rate Weekly Rate
18-Aug-2025 31-Oct-2025 7 $3,071 USD $21,500 USD
01-Nov-2025 21-Nov-2025 7 $3,221 USD $22,548 USD
22-Nov-2025 28-Nov-2025 7 $3,571 USD $25,000 USD
29-Nov-2025 12-Dec-2025 7 $3,221 USD $22,548 USD
13-Dec-2025 19-Dec-2025 5 $5,714 USD $40,000 USD
20-Dec-2025 02-Jan-2026 7 $5,714 USD $40,000 USD
04-Jan-2026 06-Mar-2026 7 $3,697 USD $25,883 USD
07-Mar-2026 27-Mar-2026 7 $3,697 USD $25,883 USD
28-Mar-2026 24-Apr-2026 7 $3,697 USD $25,883 USD
25-Apr-2026 24-Jul-2026 7 $3,382 USD $23,675 USD
25-Jul-2026 30-Oct-2026 7 $3,225 USD $22,575 USD
31-Oct-2026 20-Nov-2026 7 $3,382 USD $23,675 USD
21-Nov-2026 28-Nov-2026 7 $3,571 USD $25,000 USD
28-Nov-2026 11-Dec-2026 7 $3,382 USD $23,675 USD
12-Dec-2026 18-Dec-2026 7 $3,382 USD $40,000 USD
19-Dec-2026 02-Jan-2027 7 $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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