Review: Pineapple House At Tryall Club, Montego Bay, Jamaica


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A paradise villa on a paradise island nicely sums up what Pineapple House at Tryall Club in Jamaica has to offer and even better with 5 bedrooms, you can take your whole gang!

For a really memorable, luxury holiday, why not bring your friends and family and take over an entire villa in the Caribbean; perfect for a special occasion or even just because you’ve not caught up in a while. Pineapple House in Montego Bay, Jamaica is a stunning villa overlooking the sea with a full complement of staff. Virgin Atlantic flies direct from London to Montego Bay in just over 10 hours and the villa is just 12 miles from the airport; for a true paradise destination, this is about as convenient as you can get!


The stunning villa is perched on a hill where 180 degree views of the Caribbean Sea welcome you. It is located in the gated ground of The Tryall Club, which overlooks the ruins of the historic sugar plantation. The Tryall Club is renowned for being the Caribbean’s Finest Luxury Club Resort, and includes a world-famous golf course, tennis and its own private beach; all which you have access to as guests of Pineapple House. The exterior architecture of the villa is beautiful and looks exactly how you would expect a grand villa in the Caribbean to look. Inside it’s seriously luxurious, a recent renovation has resulted in an award-winning interior design that fits perfectly into its island location. There are 5 en-suite luxury rooms and the villa can comfortably sleep up to 10; ideal for a family travelling together or for a group of friends; it’s big enough to fit a large group but has plenty of nooks around the place to get away when you need some sanctuary! Your staff are a vital part of the experience of staying at Pineapple House; they are incredibly friendly, welcoming and attentive. You have the services of a CIA-trained chef, butler, housekeeper, laundress and gardener during your stay.


The 5 en-suite bedrooms are very conveniently the same size (250 ft²); so no fights over who gets the biggest room! Each has a private balcony or deck with sea views, air conditioning, ceiling fans and a smart TV. The rest of the villa is made up of a beautiful fully-fitted kitchen overlooking the front waterfall, rear pool and gazebo but it’s outside where you’ll want to spend most of your time; the outdoor space overlooks the stunning turquoise of the Caribbean Sea, there’s really no getting away from those views. There is a 2,500 ft² Lanai (popular in island homes, they consist of an outdoor living and dining area), so lots of comfortable seating areas, a dining gazebo for 10 and there’s even an outdoor bar! The bar overlooks the heated diving pool, 8-foot deep at one end but about half the pool is only 2-foot-deep so is perfect for children. There’s also a hot tub so if you can manage to find a quiet moment just the two of you, this is where you need to head, there’s also audio and lighting special effects so at night with a glass of something chilled romance will definitely be in the air!


Technically, you could self-cater and the professional-grade kitchen is very well equipped with a Vulcan 6-burner stove, grill and oven, side-by-side refrigerator/freezer, dishwasher, microwave, toaster, blenders, coffee maker, and abundant cookware and dinnerware; however, it’s your time off and I very much doubt you’ll feel the need to do much cooking when you have your own personal chef on standby! The chef is exceptional and nothing is off the table food-wise, tell him what you fancy or just let him get creative! If you want an occasional change from dining at the villa, then breakfast, lunch and dinner are all available at The Tryall Club too.

Pool & Activities

While I imagine it’ll be pretty hard to drag yourself (and the family!) away from the pool area it’s worth doing so as what awaits is pretty exciting too! The Tryall Club, where Pineapple House is situated, is a 2,200-acre private resort club; make the most of the fantastic facilities that can be found a mere stroll away and which include a private beach, perfect for swimming, snorkelling, kayaking and wind surfing, an 18-hole golf course, Fitness Centre, Spa, Kid’s Club and tennis. It’s a great spot for afternoon tea and the Manager hosts a Cocktail Party which is definitely not one to miss, keep an eye out for other events too. It’s easy to see why the club is ranked on the Conde Nast Gold List as one of the best places to stay in the world. To get around there are golf carts at the villa and the club also offers complimentary shuttles for transportation. If the rest of Jamaica beckons, your staff can assist with arrangements; why not visit Ys Falls, climb Dunns River Falls, swim with dolphins, visit the Appleton Distillery or if you’re feeling active, there’s horse riding, fishing, sailing, mountain biking, hiking, jet skiing, water rafting or go cliff diving in Negril!

Insider Info

Make sure you request that your chefs cook the Jerk Chicken, it’s sensational and I bet you’ll want it more than once!

For a beautiful, elegant villa to relax with your family, with wonderful staff and in a paradise spot, there are few places that can rival Pineapple House.

Pineapple House also features in our Top 3 Villas on Montego Bay, Jamaica.

Note: Benefits & upgrades subject to availability. Benefits offered correct at the time of writing. Terms & conditions apply. Enquire for more information. Posts may be sponsored by the proprietor or brand being appraised. All opinions remain our own & are in no way influenced.