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
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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
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 – Exclusive Jamaica Villa Rental at Tryall Club

Luxury Living with Caribbean Charm

Set high on Copperwood Ridge within the prestigious Tryall Club, Pineapple House is a five-bedroom luxury villa offering sweeping 180-degree views of the sparkling Caribbean Sea. Perfect for those seeking Jamaica villa rentals, this hillside retreat combines timeless design with modern comforts, just moments from the resort’s golf course, tennis courts, spa, gym, and private beach.

Elegant Accommodation

Designed in the spirit of renowned architect Oliver Messel, Pineapple House reflects a blend of classic Caribbean architecture and contemporary luxury. This Jamaica vacation villa is an ideal choice for families or groups looking for privacy and space.

Bedrooms & Interiors

  • 5 stylish bedrooms for up to 10 guests.

    • 4 king-bedded master suites with en-suite bathrooms.

    • 1 twin-bedded room (convertible to king).

    • One suite is handicap-accessible on the lower level.

  • Private balconies or terraces with panoramic sea views.

  • En-suite bathrooms and custom cabinetry.

  • Saltillo terracotta flooring throughout.

  • Smart TVs with internet access in each suite.

Outdoor Lifestyle

The villa’s design embraces open-air living, with a 2,500 sq. ft. terrace perfect for dining, lounging, or entertaining. Outdoor features include:

  • Heated infinity-edge swimming pool overlooking the Caribbean.

  • Tropical English garden with waterfall and gazebo.

  • Alfresco dining area and outdoor bar.

  • Spacious sun terrace for relaxation.

Dedicated Villa Staff

Guests of Pineapple House are looked after by a professional and attentive household team, including:

  • Private chef trained at the Culinary Institute of America.

  • Butler, housekeeper, laundress, and gardener.

  • Daily meal service featuring international cuisine and Jamaican specialties.

  • Signature cocktail: the Pineapple Painkiller, a house favorite.

Highlights of Pineapple House

  • Located in the heart of the Tryall Club Jamaica.

  • Full access to club amenities: golf, tennis, spa, fitness center, and private beach.

  • Stylish hillside villa with ocean views and luxury services.

  • Perfect choice for private villa rentals in Jamaica and family villa holidays.

  • A true blend 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

Looking for Jamaica Villas to Rent?

Looking for Jamaica Villas to Rent?Caribbean Dream Villas, a trusted Caribbean villa specialist and part of Worldwide Dream Villas, offers a handpicked selection of luxury villas to rent in Jamaica. Whether you’re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaica’s top attractions, we provide some of the finest Jamaica villa rentals available. Explore villas to rent in popular areas like Montego Bay, Negril, and Ocho Rios. With stunning ocean views, professional concierge services, and easy access to Jamaica’s best beaches, dining, and golf courses, our villas for rent in Jamaica are ideal for couples, families, and groups looking for a memorable Caribbean vacation. Book your perfect Jamaica villa getaway with Caribbean Dream Villas today!

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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