Entire home
Pineapple House in Montego Bay by Personal Villas - World-Class Service
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5 bedrooms5 bathroomsSleeps 10557.4 sq m
Popular amenities
Explore the area

Montego Bay, St. James
- Tryall Golf Club5 min walk
- Montego Bay Cruise Ship Terminal20 min drive
- Sunset Beach Resort Au Natural Beach21 min drive
- Montego Bay (MBJ-Sir Donald Sangster Intl.)36 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 King Bed
Bedroom 5
1 King Bed
5 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet · Shower only
Bathroom 5
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
About this property
Pineapple House in Montego Bay by Personal Villas - World-Class Service
Summary:
** Please drop us a message before booking the property as we need to check availability for all requests at this villa **
PINEAPPLE HOUSE at the TRYALL CLUB, Montego Bay, Jamaica
This gorgeous villa has it all; incomparable ocean views, exquisite architecture, stunning interiors, and a villa staff that deliver 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, massage center, and a short ride by the villa’s complimentary golf cart to the legendary Tryall Golf Course and the beach.
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 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.
AMENITIES
• Heated swimming pool
• Indoor/Outdoor Dining
• Hot Tub
• Free Wireless internet
• Smart TVs and Blow dryers
• Cable Flat-screen TVs
• I-pod docks and Safes
• Free on-property shuttle service
Features
• Short golf cart ride to golf, beach
• Walking distance to tennis
• Massage center and Fitness center
• Boutique and Tryall market
• Games room and Kid’s Club
STAFF
• Butler
• Chef
• Housekeeper
• Laundress
• Gardener
BEDROOM DESCRIPTION
Bedroom 1 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 2 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 3 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 4 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 5 - 2 Twin beds (which can be combined as kings), En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Mandatory Temporary Membership Dues (TMDs)
*Adults (16 & older): $184 per person per week or $36.80 per person per day for stays of less than 5 nights
Children ages 13 -15 pay 50% discounted rate
Children 12 & younger – complimentary
TMDs can be either prepaid or paid upon arrival at the Club.
*Cost quoted is inclusive of taxes.
New Temporary Membership Dues (TMDs)
* Effective immediately to all bookings for travel January 1, 2025 and beyond
1- 4 DAYS - PER DAY
16 yrs. and over - $ 34.00+ 15% = $39.10
13-15 yrs. - $17.00+ 15% = $19.55
5- 7 DAYS
16 yrs. and over - $170.00 + 15% - $195.50
13-15 yrs.-$85.00 + 15% = $97.75
*TMD rates are subject to change
Other Things to Note:
* All rates quoted in USD.
* Rates are subject to change without notice
* Thanksgiving may be charged at Premium rate.
* Villa staff is exclusively curated and included in all villa rates.
** Please drop us a message before booking the property as we need to check availability for all requests at this villa **
PINEAPPLE HOUSE at the TRYALL CLUB, Montego Bay, Jamaica
This gorgeous villa has it all; incomparable ocean views, exquisite architecture, stunning interiors, and a villa staff that deliver 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, massage center, and a short ride by the villa’s complimentary golf cart to the legendary Tryall Golf Course and the beach.
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 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.
AMENITIES
• Heated swimming pool
• Indoor/Outdoor Dining
• Hot Tub
• Free Wireless internet
• Smart TVs and Blow dryers
• Cable Flat-screen TVs
• I-pod docks and Safes
• Free on-property shuttle service
Features
• Short golf cart ride to golf, beach
• Walking distance to tennis
• Massage center and Fitness center
• Boutique and Tryall market
• Games room and Kid’s Club
STAFF
• Butler
• Chef
• Housekeeper
• Laundress
• Gardener
BEDROOM DESCRIPTION
Bedroom 1 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 2 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 3 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 4 - King size bed, En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Bedroom 5 - 2 Twin beds (which can be combined as kings), En-suite Bathroom, A/C, Toilet, Shower, private balcony or deck
Mandatory Temporary Membership Dues (TMDs)
*Adults (16 & older): $184 per person per week or $36.80 per person per day for stays of less than 5 nights
Children ages 13 -15 pay 50% discounted rate
Children 12 & younger – complimentary
TMDs can be either prepaid or paid upon arrival at the Club.
*Cost quoted is inclusive of taxes.
New Temporary Membership Dues (TMDs)
* Effective immediately to all bookings for travel January 1, 2025 and beyond
1- 4 DAYS - PER DAY
16 yrs. and over - $ 34.00+ 15% = $39.10
13-15 yrs. - $17.00+ 15% = $19.55
5- 7 DAYS
16 yrs. and over - $170.00 + 15% - $195.50
13-15 yrs.-$85.00 + 15% = $97.75
*TMD rates are subject to change
Other Things to Note:
* All rates quoted in USD.
* Rates are subject to change without notice
* Thanksgiving may be charged at Premium rate.
* Villa staff is exclusively curated and included in all villa rates.
Property manager
owner/property manager
Languages
English
Add dates for prices
Amenities
Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Sandy Bay
Located in Sandy Bay, this villa is near the beach. While the natural beauty of Jamaica Beaches and Doctor's Cave Beach can be enjoyed by anyone, those looking for an activity can explore Montego Bay Cruise Ship Terminal.
Rocklands Bird Sanctuary and Widowmaker's Cave are also worth visiting. Spend some time exploring the area's activities, including golfing.

Montego Bay, St. James
What's nearby
- Tryall Golf Club - 5 min walk - 0.4 km
- Montego Bay Cruise Ship Terminal - 20 min drive - 19.9 km
- Freeport Peninsula - 21 min drive - 20.9 km
- Sunset Beach Resort Au Natural Beach - 21 min drive - 21.1 km
- Doctor's Cave Beach - 31 min drive - 21.9 km
Getting around
Restaurants
- COLD BEER JOINT - 10 min drive
- Seaside Terrace - 9 min drive
- Mosquito Cove - 6 min drive
- Smoked Marlin - 5 min drive
- Pachie's - 3 min drive
Frequently asked questions
Reviews
Reviews
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About the host
Hosted by owner/property manager

Languages:
English
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