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 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.

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 dÃÆ'©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.

Beach and Pools
Round Hill's beach, in front of the reception area and main restaurant, is a narrow crescent of dark sand lined with palm trees and beach loungers. For beach-lovers, it can be a bit of a disappointment since it's not a very large beach. But the water here is clear, warm and lovely, and there are plenty of complimentary toys on hand - Hobie Cat, kayaks, paddle boards - that make a dip extra inviting.

For those who prefer to lounge by their villa pool or the resort's infinity-edged pool, the small beach isn't a problem. Older kids who spend most of the time in the water may not even notice the small swath of sand. They might be too busy swimming out to the trampoline, kayaking or racing each other on pedal boats. The resort can also arrange snorkeling outings and guided dives to nearby reefs, as well as water skiing and tubing. 

In addition to the many villas with their private pools, Round Hill also has an infinity edge swimming pool directly overlooking the ocean that's open to everyone and located right next to a shallow children's wading pool. There are no lifeguards on duty at the main pool or kids' pool.

Water Sports
Non-motorized water sports are complimentary here - including snorkeling, pedal boats, Hobie Cats, paddle boats and sea kayaks. You're asked to sign up to use them and grab a lifejacket at the small deck area on the west end of the beach, but there's hardly ever a line to partake. Tubing, water skiing, wind surfing lessons and snorkeling and scuba diving outings can also be arranged here for an additional fee. Water sports are available from 9 a.m. to 4 p.m.

Pineapple Kid's Club
Round Hill offers two year-round, complimentary supervised children's programs for varying age groups. Both clubs use the air-conditioned cottage on the lawn near the lobby as a base. The first two rooms, a main area with craft tables, board games and a blue sky ceiling painted with red, blue and green balloons, as well as a small side room, are for the "Pineapple Kids," ages 3 through 6 (kids must be potty trained). From 9 a.m. to 5 p.m., the younger kids enjoy movies, face painting, and T-shirt painting inside. Kids also fly kites, play beach games and go on nature walks throughout the property.

At the "7-up Club" for ages 7 and older, also from 9 a.m. to 5 p.m. can play Foosball and computer games in the rear two rooms of the cottage, as well as take advantage of Round Hill's facilities by playing volleyball and taking tennis clinics. These kids also enjoy dance lessons, basket weaving and video game tournaments. There's Xbox and a foosball, table as well as a mini billiards table for the older kids here, too.

Walking Paths
The resort has a jogging/walking path that's about 1-mile long. It passes the garden where the chef grows lettuce, spinach, callaloo, tomatoes and a variety of herbs for the restaurants. Just beyond, on top of the round hill is a bench with a splendid view of the sea. 

Tennis
Tennis and equipment are complimentary and the resort has five all-weather courts. Golfers tee up at Tryall's nearby course, to which the concierge can arrange complimentary transport.

Spa
Teens and tweens ages 12 to 16 can enjoy the resort's All About Me Teens' Spa treatments. These include mini-massage, facials, manicures, pedicures and hair braiding.

There's really one restaurant at Round Hil, the Seaside Terrace. And unless you're staying in one of the villas and have meals whipped up by your personal chef, you may tire of the menu after a week.

In-Room Dining
Ah, the cook! Rent a villa and he or she prepares breakfast for you, a leisurely start to the day. You can also request your cook prepare additional family meals.

The Seaside Terrace
This roof-top restaurant features an indoor wood-fired grill (one of the only ones on the island) and serves modern Caribbean cuisine. Seafood is a favorite here. The restaurant has continual service from 7:30 a.m. to 10:30 p.m. daily.

The restaurant runs a buffet breakfast daily on the roof deck with a great Jamaican juice bar, omelet station, pastries, bagels and many hot selections. Lunch sticks to things like burgers, salads, fish sandwiches and the like. And dinner is fancier with some great steaks and seafood on the menu. You can opt to eat lunch or dinner upstairs on the roofdeck or downstairs on the sprawling terrace. Kid-friendly items include burgers, fish fingers, pizzas, pasta, sandwiches, mac and cheese and the like, all priced around $10 to $12.

Beach Barbecue
On Mondays, the resort offers a beach barbecue and on Fridays, the property hosts Jamaican Night with stilt walkers, Limbo contests and Jamaican food. Extra fees apply.

Round Hill offers a variety of packages, some of which include meal plans.

All About the Extras
Complimentary Snacks
We love the complimentary daily afternoon tea served at 4 p.m. on the patio outside of the lounge. Along with the tomato and cheese sandwiches and cucumber sandwiches, there's a nice array of cookies, cakes and sweets to please parents and kids. It makes for a nice carry-me-over between lunch and dinner.

Wi-Fi
Wi-Fi service is complimentary throughout the resort. In addition, the property has a library with one computer and use is complimentary. 

Fitness Center
The state-of-the-art fitness center and open-air yoga pavilion, located near the spa, feature fitness with a view. Several cardio machines are offered, plus free weights and a personal trainer. Yoga and fitness classes can also be found here. Kids ages 16 and older may use the facility. The gym is open from 5 a.m. to 10 p.m.

The Art of Smart Timing
High season runs from around mid-December to mid-April. The resort no longer has a shoulder season. Rates drop to low season after mid-April and continue through Labor Day. After Labor Day, the resort closes for the month of September and re-opens in October. Low season continues from October to mid-December. Long-time staff members tell us that June and October are the island's rainiest months. 

Getting There
Round Hill is located in Montego Bay, about a 25-minute drive from Donald Sangster International Airport. Round Hill can arrange transfers or guests can take a local taxi to the resort. It's about $45 (one way) for one to four people and an additional $12 for each extra passenger.

Getting Around
The resort provides free regular shuttles to Montego Bay and to golf at Tryall, another villa resort nearby.

For Mom and Dad
Spa
Take advantage of pampering treatments at the Spa at Round Hill. You reach the spa by following a footpath that leads from the resort's waterfront to the next cove. The spa building sits atop a rise fronted by an expansive green lawn that stretches to the ocean. A designated "quiet area" open to adults only, the entire spa lawn is a great place for relaxing under one of the huge almond trees (you don't need to have a treatment to use the space). There's a hammock and a small outdoor pool here, too, as well as a few day beds fronting the ocean for relaxing (the beach isn't the best for swimming, as it's covered with rocks). The spa building was created from the original stone manor house, parts of which date to the 18th century.

The spa has seven treatment rooms plus an outdoor, hillside couples' hydrotherapy area hidden behind lush vines.

For a casual dinner offsite, ask the concierge to book you a table (must be reserved in advance) at a rustic seafood restaurant just down the beach. At the Lobster Trapp, local fishermen cook up lobster they've just hauled in that morning. You've never tasted shellfish this fresh.