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