Pineapple House
Overview
Specials
Amenities
Location

Pineapple House

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10   5
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Villa
10 Guests
5 Bedrooms
6 Beds
4 Bathrooms
2 floors
Tryall Club, Montego Bay, Jamaica, Caribbean
Villa
Ocean View
Pool with heating
Hot Tub

Special Offers

One Love Lives
The spirit of Jamaica endures and welcomes you back. Book this home and enjoy $1,000 in savings on stays through the end of April. Beautiful surroundings, warm hospitality, and the rhythms of the island await your return.
Offer applicable:
Stay: Feb 7 — Oct 31, 2026

About This Property

This gorgeous villa has it all; incomparable ocean views, exquisite architecture, stunning interiors, and a villa staff that delivers a level of hospitality that is nothing short of world-class.

Pineapple House is nestled on the brow of Copperwood Ridge, overlooking an extensive portion of the Tryall Club 18-hole golf course and with 180 degree views of the Caribbean Sea. It is within easy walking distance of the Great House, gym, tennis courts, spa and a short ride by the villa’s complimentary golf cart to the legendary Tryall Golf Course and the beach resort club.

Beautifully built and designed in the spirit of the renowned architect Oliver Messell, Pineapple House is built on two levels and has all of the hallmarks that you would expect from a villa of this quality, style and comfort.

There are four master bedrooms fitted with King beds and one bedroom fitted with twin beds which convert to a king. All master suites are of the same size and come with custom-designed cabinetry, Saltillo-terracotta tiled floors and lavish en-suite bathrooms. The lower level master bedroom which has a king size bed is handicap-accessible. Smart televisions with internet capability are installed in each suite. Each bedroom has a private balcony or deck with thrilling views.

The villa is notable for its views and the spacious verandas from its upper floors, 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. Well-manicured lawns are great spots for the children to play and the English garden with its waterfall is the loveliest place to sit and read or host a cocktail party.

A warm and efficient team of Chef, Butler, Housekeeper, laundress and gardener, wait to serve you with everything you could possibly want, plus endless rounds of the House drink, “Pineapple Painkiller.” You will not want to leave. Chef Rannoy is a certified chef from the Culinary Institute of America, the world-renowned premier cooking school that has trained some of the best chefs in the world. A talented professional, Chef Rannoy will prepare and present the most mouth watering meals for you to enjoy.

The Tryall Club Experience
Guests of this villa enjoy access to the prestigious Tryall Club, set across 2,200 acres of beautifully landscaped hillside and beachfront. Amenities include the renowned 18-hole championship golf course, tennis courts (day and night play), private beach club, fitness center, jogging trails, Kids Club, and complimentary non-motorized watersports such as snorkeling, kayaking, and sailing. Guests also enjoy afternoon tea at the Great House and weekly social events including the Manager’s Cocktail Party.
*While many facilities are included, additional fees apply for golf, spa services, dining and bar charges, motorized watersports, and select special events.

Temporary Tryall Membership Dues

All villa guests are required to register for a Temporary Membership during their stay. Current rates are US$170 per person (16+) per week, or US$34 per person per day for stays under 7 days (plus 15% service charge). Children 13–15 receive a 50% discount; children 12 and under are complimentary. Fees are payable directly to the Club upon arrival.
*Please note that certain facilities may occasionally close for private events, and membership offerings and fees can be subject to change at any time without notice.

Bedrooms and Amenities

Bedrooms

Bedroom One
Bed: King Bed·En-Suite Bath·Direct Access to Private Balcony·Flat-Screen, Smart TV·Ocean View
Bedroom Two
Bed: King Bed·En-Suite Bath·Direct Access to Private Balcony·Flat-Screen, Smart TV·Ocean View
Bedroom Three
Bed: King Bed·En-Suite Bath·Direct Access to Private Balcony·Flat-Screen, Smart TV·Ocean View
Bedroom Four
Bed: King Bed·En-Suite Bath·Direct Access to Private Balcony·Flat-Screen, Smart TV
Bedroom Five
Bed: 2 Twin Beds w/Option as King Bed·Ocean View

Amenities

Living Room
Sofas·Flat-Screen, Smart TV·Bar·Multiple Seating Areas
Kitchen
Fully Equipped Kitchen
Dining Area
Dining Table - Seats 10·Ocean View
Outdoor Living
Pool·Hot Tub·Chaise Lounges·Outdoor Dining Table·Gazebo·Garden·Manicured Yard·Waterfall·Deck·Veranda
Home Amenities
Air Conditioning·Wireless/WiFi Internet Access·iPod Docking Station·Safe·Hair Dryer
Services Available
Butler Service·Chef Service·Gardener·Housekeeper·Private Laundry Service
Home Amenities Three
Transportation
Complimentary Shuttle·3 Golf Carts

Location

Attractions

Sangster International Airport
14.7 Miles
Nearest Airport
Tryall Club
0.5 Mile
Beach, Restaurants, Golf Course, Kids Club
Round Hill Resort
4.6 Miles
Golf Course, Tennis Court, Spa, Gym, Trails, Beach Access, Kids Club
Hip Strip
13.1 Miles
Shopping & Restaurants, Sightseeing, Adventure & Exploring
Aquasol Theme Park
13.1 Miles
Amusement Park, Ocean Gear Rentals, Go-Kart Racing, Water Sports
Doctor's Cave Beach
13.6 Miles
Beach, Beach Club, Beach Access
Ahhh...Ras Natango Gallery and Garden
15.8 Miles
Nature Preserve, Galleries, Lookout
Cinnamon Hill
22.5 Miles
Golf Course
Kool Runnings Waterpark
31.8 Miles
Amusement Park, Water Park
Royal Palm Reserve
34.8 Miles
Botanical Garden
$3,225 — $5,714 / night
Pineapple House
Tryall Club, Montego Bay, Jamaica, Caribbean
·
10   5
$3,225 — $5,714 / night
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This property requires our Villa Specialists to confirm availability for you. Please inquire below.

For assistance call us at 888.628.4896

Rates

Please note, quote is not inclusive of Temporary Tryall Membership Fees due at the property upon check-in. Please inquire with your Villa Specialist for current rates.

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