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Our Travel Planners are here to help you book your perfect
Welcome to Hillside House on Round Hill, nestled in the picturesque region of Hanover Parish, Jamaica. This magnificent five-bedroom retreat offers a perfect blend of Old Jamaican charm and modern luxury, making it an ideal hideaway for families and groups of up to ten guests. Each bedroom boasts its own en-suite bathroom, with several offering king-size beds and outdoor access, ensuring a private and relaxing stay. The property captures the essence of island living with breathtaking panoramic ocean views and the gentle caress of cooling trade winds. Designed with elegance and comfort in mind, Hillside House provides a relaxed yet refined atmosphere where guests can unwind and savor the tranquil island surroundings.
The property is equipped with an array of luxurious amenities to make your stay truly unforgettable. Stay connected with complimentary Wi-Fi and enjoy leisurely days lounging by the private ocean-view pool, complete with sun loungers for soaking up the Jamaican sun. Delight in culinary experiences crafted by your personal cook and receive first-class service from a team of staff including a butler, housekeeper, laundress, and gardener. Emphasizing leisure and relaxation, Hillside House features smart TVs, a balcony or terrace for delightful outdoor moments, and exclusive memberships to the Round Hill and Tryall Clubs, enhancing your island experience. Whether you're invigorating your senses with the outdoor shower or enjoying a peaceful evening by the fire pit, this property offers a luxurious sanctuary that celebrates the best of Jamaican hospitality.
A special amenity available to guests in this villa is membership at Round Hill, just minutes from the villa and one of the finest private resorts on Jamaica's North Coast.
Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, and unforgettable long sunsets from the waterfront terrace.
Guests receive complimentary use of the Round Hill gym; the $25 daily fee is waived for Hillside House guests (paid for by the homeowner). Hillside House guests also receive complimentary WiFi throughout Round Hill (daily fee waived/paid by the homeowner).
For additional charges, members may enjoy the spa, tennis courts, afternoon tea, and Wednesday Manager's Cocktail Party, Pineapple Kids Club, fitness center, salon, a range of water sports, and beach parties.
A significant amenity for guests in this villa is membership at the excellent Tryall Club. On 2,200 acres, Tryall’s golf course is among the most beautiful in the world. Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda, and other PGA championship events. The resident pro offers workshops and private lessons. The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pros on call. All white attire required.
The beach is well planned for parents and children. Have lunch at the beach bar. Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it). Jog the marked trails. Snorkeling, kayaking, Hobie Cat, and sunfish are complimentary. Glass bottom boats, charter fishing, a boat to the reef, and any captained craft attract various fees. Enjoy weekly events like complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.
On the hill, enjoy the historic Great House for daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar. Also at the Great House is the new Usain Bolt Games Room, open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs, and HDTV. And don’t miss the massive Tryall pool. The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads, and everyone from teens to octogenarians.
Available to purchase on checkout
If you have any queries or need further information, you can contact us anytime via live chat or telephone. Our Travel Planners will be happy to help in any way they can.
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1-407-495-2595
24 hours a day
7 days a week