Round Hill Hotel and Villas Review

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416 Family Reviews
John Pringle Drive, Montego Bay, Jamaica
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Editor’s Review of Round Hill Hotel and Villas

As our taxi turns into Round Hill's drive, we look beyond the casuarina trees to the green, round hill -- the resort's namesake -- laced by turquoise waters. We then pass a series of villas, their white frames barely visible behind the tall palm and almond trees. When we reach the lobby, a smallish white building whose open-air foyer gives onto an inviting view of the Caribbean Sea, the staff welcomes us with big smiles and our choice of rum or fruit punch.

Situated on a former pineapple plantation and sprawling across 40 acres, Round Hill Hotel and Villas, in the Montego Bay area is the epitome of Caribbean elegance. The property debuted in 1953 as a series of cottages that were individually owned, typically by the wealthy and
... more well-connected. When the notables weren't in residence, their equally high-profile friends were. In the resort's heyday, you might find Adele Astair, Oscar Hammerstein, Cole Porter or Noel Coward in the lounge or Bill and Babe Paley sunning at their cottage's pool. Their black and white photos can still be seen in the property's elegant common areas.

Today, the 27 individually owned villas (most available for guest stays and ranging from two to six rooms)) are still the property's gems, and the prime pick for a family stay. But the 36 hotel rooms in the Pineapple House, overlooking the pool and sea, make for a sublime family escape for smaller groups, too.

These days, the celebrity you hear about most here is Ralph Lauren. The fashion designer owns the stark white villa on the round headland from which the resort gets its name, as well as another villa on the property. And his expertise was invoked in 2006 redesign of the clean, bright and contemporary rooms in the Pineapple House.

While Round Hill still attracts those accustomed to the spotlight as well, as those with deep pockets -- ask which villa Paul McCartney prefers when vacationing -- the resort's feel of "exclusivity" is somehow a very approachable and friendly one. And that's a good thing for families, who really get the red carpet treatment here. less
Our Editor Loves
  • Extra space and privacy in a villa
  • Complimentary children's programs
  • Complimentary non-motorized water sports
Family Interests
    Family Amenities
    • Babysitting
    • Children's Program
    • Connecting Rooms
    • Cribs
    • Family Room 5+
    • Free Wi-Fi
    • Kids'/Theme Meals
    • Kitchenettes
    • Laundry Service
    • Meal Plan
    • Onsite Dining
    • Refrigerator
    • Pool
    Our Member Reviews 416 Reviews
    Caitlin's Mom
    This was our second visit to Round Hill, and I have to say it's becoming a favorite for our family. Perfect if you're looking for an easy all-inclusive resort for chillaxing that's small, low key, tranquil and has great food and ...
    Read full review


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    The villas, the resort's gems, are what make Round Hill special. A stay in one of the two- to six-bedroom villas provides your family with the outdoor space of decks, private lawns and sometimes private pools. You have the convenience of a full kitchen and breakfast prepared for you in your villa by a cook. You can arrange to have additional meals cooked for you, and some of the larger villas come with a housekeeper, as well as a cook and a gardener. 

    Often the villas come with an indoor and an outdoor living area complete with billiard tables and nooks for lounging with views. Some villas offer great sea views. As a result of the outdoor/indoor arrangement, most of the villas have air-conditioning in the bedrooms only. The common area rooms have ceiling fans. All bedrooms in the villas come with private ensuite bathrooms and terraces, so they really feel like complete hotel rooms. And indeed if a villa isn't already rented out, you can request to stay in just a room or two in some of them - with access to the entire property and private pool as a bonus.

    Lush gardens surround most of the villas, creating a sense of privacy. Depending upon the villa, you can sit on your deck, admire the splendid sea view and feel as if you are the only family at the resort.

    Celebrity Stays
    Sir Paul McCartney has stayed a few times in villa #17, a four bedroom unit. In the kitchen, look for the photograph of him and his young daughter Beatrice surrounded by the cottage's staff. A bedroom with a private bath flanks either side of the living space that faces the pool. Each of the two downstairs bedrooms comes with private baths, as well as portholes that look into the pool -- an interesting feature. 

    We're told that John F. Kennedy and his bride Jacqueline honeymooned in villa #10 and the future president practiced his inauguration speech in villa #25. Villa # 11 had a role in "How Stella Got her Groove Back." And villa #20 is one of our all-time favorites. With six beautiful bedrooms, two pools and sweeping views west along the coast, it's perfect for a multiple-family or multi-generational getaway.

    Split Villas
    Sometimes the resort splits a larger villa, renting a bedroom and bath on one side to one family and the bedroom and bath on the other side to another family. The guests share the common sitting area, the kitchen and the pool. This can be great if you know the other family, but an inconvenience if you don't (and don't enjoying listening to someone else's music bumping over the sound system at the pool, for example). Be sure to ask if your rental is for the entire villa or just part of it. 

    Villa Decor
    Since the villas are individually owned, the decor varies. But you can count on extra tasteful and luxurious Caribbean-minimalist dÃ'©cor throughout. Most villas combine dark wood four-poster beds with rattan furnishings and comfortable couches. Bathrooms are tiled and some have oversized tubs.

    Villa Pools
    Superior or classic villas do not have pools. The pineapple suites have large bedrooms, but just semi-private pools; master villa suites are larger, also with semi-private pools.

    Pineapple House
    Small families (max three guests ) can also opt to stay in one of the 36 rooms in the Pineapple House, which feels more like a traditional hotel stay. While many of the villas are quite a far walk from the restaurants, the Pineapple House is smack dab in the middle of it all, and may be the best option for mobility if your child is young. Although the upstairs rooms in the two-story building offer better views of the ocean and are spacious with their vaulted ceilings, we like the downstairs rooms best because these come with balconies or patios that let you really relax and admire the views. The rooms were renovated in 2006 and decorated by Ralph Lauren, who also owns a villa at Round Hill.

    The hotel rooms feature an inviting blend of dark wood and dark bamboo furnishings paired with white daybeds, floors and chairs accented with spots of color. Rooms with a king bed or two double beds are available. Two white swatches of fabric drape the four poster bed and a red throw makes reading in the chair feel even more cozy. A young child would find the daybed comfortable, but a teenager might grumble. Three is the maximum occupancy for each of these rooms, but you can request an extra bed if you need one or are traveling with an older child who won't be comfortable in the day bed.

    Note: Be aware that none of the lodgings have televisions. If you can't miss your favorite show, you can watch it at the television room near the restaurant (provided any other guests on hand are fine with your choice in programming, of course).

    Connecting Rooms
    Only one pair of rooms connect in the Pineapple House - a king room to two doubles.

    Rollaway Beds and Cribs
    Extra beds can be added to rooms or villas for $79 daily, plus tax. Cribs are free of charge.

    ADA Rooms
    Downstairs rooms in the Pineapple House have roll-in showers that are good for most people with mobility issues -- ask for one closest to reception to shorten your walk.


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