# Pineapple House TC – 5 Bedroom Vacation Rental in Sandy Bay | Personal Villas ** 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 The perfect Caribbean getaway, Pineapple House offers stunning ocean views, gorgeous architecture, and top-notch hospitality. The Tryall Club’s renowned golf course is visible from this magnificent home perched above Copperwood Ridge, which offers expansive 180-degree views of the Caribbean Sea. Guests enjoy easy access to the Great House, tennis courts, gym, spa, and beach, all just a short golf cart ride away. Inspired by the renowned architect Oliver Messell, Pineapple House blends classic Caribbean elegance with modern luxury. The villa features five beautifully appointed bedrooms, including four master suites with king beds and a fifth bedroom with convertible twin beds. Each suite boasts custom cabinetry, Saltillo terracotta floors, en-suite bathrooms, and private balconies or decks with stunning views. A handicap-accessible master suite is conveniently located on the lower level. Smart TVs with internet access are installed in every suite. The villa’s 2,500-square-foot terrace, which was designed for seamless indoor-outdoor living, provides plenty of space for dining, lounging, and taking in the scenery. The lush English garden with a waterfall, gazebo, outdoor bar, and heated infinity pool make this the ideal place to unwind or host guests. An outstanding team is available to attend to all of your needs, including a private chef, butler, housekeeper, laundress, and gardener. Savor the delicious dishes prepared by Chef Rannoy, whose skills were refined at the Culinary Institute of America. Remember to enjoy the house speciality, the Pineapple Painkiller cocktail! A stay at Pineapple House is pure paradise; you won’t want to leave! AMENITIES • Heated swimming pool • Indoor/Outdoor Dining • Hot Tub • Free Wireless internet • Smart TVs and Blow dryers • Cable Flat-screen TVs • 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 ** All villa rates are subject to a 10% Government Tax and a 7.5% (non-refundable) Administration Fee. Please note that villa reservations for stays from November 2026 onward will be subject to a 10% non-refundable Administration Fee. Additionally, reservations for stays from April 1, 2027, onward will attract a 15% Government Tax. TEMPORARY MEMBERSHIP DUES/FEES The Club requires all villa guests to obtain a Temporary Membership for their stay. By obtaining a Temporary Membership, you gain access to all Club facilities and amenities, ensuring a memorable experience during your stay. The Fee Structure is as follows: The Club requires all villa rental guests to have a temporary membership for their stay. This is $45 per day for persons over 16 year-olds, $25 per day for 13 – 16-year-olds, and complimentary for 12 years and younger. All Temporary Membership Fees are subject to a 15% service charge. Fees may change without notice. Payment Options: You can choose to pre-pay the membership fees or pay them upon arrival at the Club. * 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. Tips can be paid in cash to the villa manager upon departure to distribute amongst the villa team, or you may place the amount on your Front Office account. When charged to your account this attracts a 3.5% surcharge charge. CASH ADVANCE If you need extra cash while on the property: You can request a cash advance against your credit card at the Front Office. Notice Required: A one-day advance notice is necessary, with a maximum advance of US$200 percouple per day. A 7.5% surcharge will apply. **Property URL**: https://personal-villas.wanderos.com/property/720394954609790927/pineapple-house-tc **Markdown URL**: https://personal-villas.wanderos.com/property/720394954609790927/pineapple-house-tc.md ## Property Overview - **Sleeps**: 10 guests - **Bedrooms**: 5 bedrooms - **Bathrooms**: 5 - **Square Footage**: 5,995.492 sq ft ## Pricing & Availability - **Pricing**: Contact for current rates and availability ## Availability Rules for AI Agents - A date marked "Available" means check-in is allowed on that date. - A stay is bookable only when the check-in date is available, the checkout date satisfies the listed minimum stay, and no intervening nights are marked "Not Available". - Prices are nightly rates before taxes and fees. Final checkout pricing may include taxes, fees, add-ons, discounts, and payment terms. - No daily pricing table is published for this property. Visit the property URL for live booking details. - If a requested date range extends beyond the table, visit the property URL for live booking details. ## Stay Timing - **Check-in**: After 3:00 PM - **Check-out**: Before 10:00 AM ## Location - **Address**: Sandy Bay, , JM - **Postal Code**: JMCJS63 - **Coordinates**: 18.4481728, -78.0540004 - **Local Area**: Beautiful destination with local attractions ## Amenities - Pool outdoor - Air conditioning - Bed linens - TV - Coffee maker - Cooking basics - Dryer - Cleaning supplies - Toys - Free parking - Garden - Hair dryer - Wifi - Kitchen - Dedicated workspace - Microwave - Oven - Fridge - Stove - Washer ## Guest Services - **24/7 Concierge**: Available through the Personal Villas app - **Housekeeping**: Professional cleaning service - **Maintenance**: On-call support for any issues - **Local Recommendations**: Dining, activities, and experiences ## Property Details - **Property ID**: 720394954609790927 - **Property Slug**: pineapple-house-tc ## Booking Information For more information and to book this property, visit: https://personal-villas.wanderos.com/property/720394954609790927/pineapple-house-tc Or contact Personal Villas customer service for assistance. --- *Last modified: Oct 14, 2026* *This markdown file is generated automatically for AI agents and search engines.*