A Posh Family Beach Vacation at Jamaica’s Round Hill Hotel & Villas

Jamaica has always been noted for its warm hospitality, and I can’t think of anywhere on the island that epitomizes it better than Round Hill Hotel & Villas. Tucked amid 100 acres on a peninsula near Montego Bay, it radiates an easy elegance and graciousness that draw generations of families back over and over. Repeat guests are greeted by hugs and personal hellos; visit more than once and the staff will remember your drink preferences, your favorite room and the names and ages of your little ones. Although the hotel evokes the dignified air of a country club, it’s anything but stuffy. You’re in the Caribbean, after all, and luxury here marches to its own leisurely beat.

Property overview at Round Hill, Jamaica

Round Hill occupies a lush cove not far from Montego Bay — a perfect blend of seclusion and easy access.

Round Hill Hotel & Villas Review

Round Hill is just 20 minutes from the Montego Bay airport, but as soon as you drive through the gates and up the steep, twisting road, you’re a world away from the hustle and bustle. It’s so private that, if I had tweens and teens, I’d have no problem letting them roam the grounds on their own. The property opened in the 1950s, and its blend of seclusion and sophistication made it a magnet for the glitterati: Noel Coward, John and Jackie Kennedy, Oscar Hammerstein et al. Photos on the walls of the cocktail lounge are a who’s who of A-list guests over the years. While it’s retained its glamorous cachet, Round Hill warmly and thoughtfully caters to families. Kids aren’t tagalongs here — they’re mini VIPs. One little boy, whose family has visited every year since he was a baby, has his own engraved name tag and gets to zip around the property with the staff. How sweet is that?

Pineapple House at Round Hill, Jamaica

The Pineapple House offers king and double guestrooms that can be connected for families.


Round Hill’s accommodations are stunning. The two-story Pineapple House has 36 guest rooms, which connect for families of up to five people (larger groups will need a villa). Ralph Lauren, who owns a home on the property, masterminded the decor: dabs of sapphire blue and hot pink in a field of crisp, clean white. Mahogany four-posters, slatted wood ceilings and sleek stone flooring complete the island-preppy effect. My room was on the second floor and had a knockout view of the water. There are no TVs in the rooms, but who needs them when you can lounge in an oversize club chair, watching the sun slip below the horizon and the lights flicker on across the bay? Ground-floor rooms have private patios that look out to the oceanfront infinity pool and adjacent kids’ pool. Despite the proximity to the guest rooms, pool noise isn’t really a factor, even with the shutters wide open.

Oceanfront room at Round Hill, Jamaica

Second-floor rooms in the Pineapple House have fantastic, sweeping sea views.

Villa Suites and Private Villas

Round Hill has 27 villas tucked into the hillside. All of them are individually owned and decorated, but they adhere to the same casually elegant style — lots of blue and white, wicker and bamboo, and tailored top notes. They range from two to six bedrooms, with full kitchens and, in most cases, private pools. To pamper you even further, each comes fully staffed with a housekeeper, cook and gardener — you don’t have to poke a toe beyond your peaceful bubble. Should you feel like venturing out, the staff will ferry you around the property in a golf cart.

Villa living room at Round Hill, Jamaica

Villas are individually owned and decorated, but all feature crisp, classic decor.

I toured a representative sample of villas, and I think some work best with either very tiny babies or older kids (open stairs, living areas that merge with the pool deck, and so forth). With toddlers and preschoolers, I’d choose one with an easier configuration. Ask about the different floor plans before you decide on which villa to book. If you don’t need a complete villa, you can reserve a portion of one as a suite. Just know that if someone else books the other part, you’ll be sharing common areas such as the kitchen and pool. Happily, Round Hill pays special attention to the mix of guests in these cases (they try not to put, say, honeymooners together with extended families).

Villa pool at Round Hill, Jamaica

Private pools and green spaces at the villas give families plenty of space to play.

Beach and Activities

Round Hill’s beach is compact, but it’s sheltered, private and tranquil — exactly what I want from a Caribbean hotel. The shallows are roped off for swimming. To explore farther out, flag down the watersports staff, who can set you up with kayaks, Hobie-Cats, snorkeling and scuba gear, banana boats, and more. The hotel has its own glass-bottom boat, which cruises over the reefs nearby, as well as a speedboat that guests can charter. Not in the mood to get wet? Join a fitness class, play a round of golf at a course nearby, tour the property’s lavish gardens, or brush up on your tennis backhand. A beautiful path winds along the bay to the spa, an adults-only oasis. The spa building was under renovation during my stay, but as far as I could tell, the new facilities will be stunning. Meanwhile, several guestrooms in the Pineapple House have been converted into treatment rooms; I indulged in a massage and emerged a very content wet noodle.

Infinity pool at Round Hill, Jamaica

Round Hill’s infinity pool. Feel yourself exhaling?

Kids’ Club

Activities at the kids’ club, a simple little cottage at the heart of the grounds, are included in the room rates. It’s divided by age: the Pineapple Club for 3- to 6-year-olds and the 7-up Club for bigger kids up to 12. The schedule changes every day: beach volleyball, nature walks, crafts and games, shell hunting, dance classes, movies and more. Certified nannies staff the club, and you can also book them privately for a minimum of 3 hours at a stretch. They aren’t just for babies and toddlers — it’s not unusual to see them supervising school-age kids and up, many of whom have come to Round Hill for years and request the same nanny each time. Best of all, they’re available around the clock for couples who want to linger over a nightcap, or for parents who need a break from predawn wake-up calls. Now that’s luxury!

Kids' club at Round Hill, Jamaica

Activities at the Pineapple Kids’ Club, such as learning traditional basket-making from a local artisan, change daily.

Dining at Round Hill

I’ve stayed at five-star Caribbean hotels where the food fell flat, but Round Hill isn’t one of them. Every single thing I tasted was delicious and well prepared. Much of the produce comes from the organic garden onsite, and seafood and other goods are sourced locally. The menu at the open-air Grill offers an inspired take on island cuisine — don’t-miss dishes include sautéed callaloo greens, spiny lobster grilled over Jamaica’s native pimento wood, and Scotch bonnet pepper ice cream. Although the Grill is elegant and has a dress code, you won’t feel out of place with little ones in tow. There’s a kids’ menu and early dining hours to accommodate families. The Seaside Terrace just outside the cocktail lounge serves a casual lunch menu. Villa guests can have breakfast prepared in-house and can order in lunch and dinner from the restaurant menus if they wish. For all guests, the staff serves an informal afternoon tea, including finger sandwiches, cakes and pastries, fruit and other nibbles to go with your Earl Grey. It’s a perfect amenity for kids (and, let’s be honest, some grownups) who get cranky in the late-day lull. This is Round Hill in a nutshell: refined niceties tempered by laid-back tropical charm.

Cocktail lounge at Round Hill, Jamaica

Round Hill’s cocktail lounge hosts afternoon tea as well as evening drinks.

Want Help Booking a Room at Round Hill Hotels & Villas?

If you make a request using Ciao Bambino, the request goes right to the hotel for the best available pricing and one of our Family Vacation Consultants will follow up with you to ensure all your needs are met. This is a free service! Just use the Check Availability button on the Round Hill Hotel and Villas family-friendly review in the CB! Collection to make your request. Need help planning a full Caribbean family vacation? We can help! Our Family Vacation Consultants provide expert advice on the best accommodations and activities for your family. Request assistance on My Trip Planner. Relevant Links: Ciao Bambino family-friendly review of Round Hill Hotel & Villas Essential tips for a Caribbean family vacation Jamaica with kids Six Caribbean islands for kid-friendly bliss Family beach vacation ideas Editor’s Note: Lisa was hosted by Round Hill Hotel & Villas to review the property for Ciao Bambino. As always, our opinions are our own. Photos by Lisa Frederick.

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