Two Jamaican Icons: Half Moon & Round Hill – Which Resort Fits Your Family?

When it comes to luxury family travel in Jamaica, two names consistently rise to the top: Half Moon and Round Hill. Both are legendary properties with decades of history, devoted followings, and that effortless Caribbean elegance that makes you forget about email the second you arrive. I recently had the privilege of experiencing both as a travel advisor, and I'm excited to share what makes each of these resorts so special for families.

Getting There

Half Moon sits in Montego Bay, just a quick 10-minute drive from the airport—which is clutch when you're traveling with kids who've already asked "are we there yet?" seventeen times on the plane. The 400-acre estate hugs a pristine crescent-shaped beach (hence the name), and the property feels like its own self-contained village.

Round Hill is about 30 minutes west of Montego Bay in Hopewell, more secluded and perched on a hillside overlooking a stunning private cove. The drive gives you time to decompress and really feel like you're escaping. Both locations offer that classic Jamaican beauty, but the vibe shifts based on how quickly you want to transition from airport to beach mode.

Accommodations for Every Family Style

Both resorts offer a range of options from traditional rooms to sprawling private villas, so let's break down what you're actually getting at each level.

Entry-Level Rooms & Suites

Half Moon's Garden View and Oceanfront Rooms are traditional hotel-style accommodations—comfortable, well-appointed, and perfect for couples or families with one small child. They're your classic resort room experience with all the amenities you'd expect from a luxury property.

Round Hill's Pineapple House rooms are also the entry point, but with a key difference: they're right on the beach. These oceanfront accommodations put you steps from the sand with elegant, classic Caribbean styling. The location alone makes them feel more special than a standard hotel room, and they work beautifully for smaller families who want that beachfront access without the villa price tag.

Stepping Up: Suites

If you need more breathing room, Half Moon's one-bedroom suites give you a separate living area and significantly more square footage. Some overlook the ocean, others nestle into the gardens—it's really about whether you want to fall asleep to the sound of waves or prefer a quieter retreat.

Round Hill's Premium Oceanfront Suites offer more space and those jaw-dropping ocean views that make you want to camp out on your balcony. They strike that sweet spot between a standard room and a full villa commitment.

The Villa Experience

This is where both properties really shine, but in different ways.

Half Moon's villas range from two to seven bedrooms and are scattered throughout the property. Many come with private pools, full kitchens, and dedicated staff. They maintain that connection to the resort—you can easily access all the amenities, restaurants, and activities—while still having your own private sanctuary. It's perfect for families who want the best of both worlds, or for multi-generational groups and families traveling together who want to split costs.

Round Hill's 27 hillside villas are something else entirely. Each one is privately owned and uniquely decorated (Ralph Lauren designed his own, if that gives you an idea of the caliber). They range from one to six bedrooms, all with private pools and personal staff who cook, clean, and basically ensure you never lift a finger. These villas offer total privacy and that home-away-from-home feeling, though you're a short walk or golf cart ride from the beach. The individual character of each villa means no two stays are quite the same.

Family-Friendly Features and Activities

The approach to families differs beautifully between these two properties, and both work depending on what your crew needs.

Half Moon leans fully into the family-friendly experience with their Anancy Children's Village—a supervised kids' club complete with activities, a small pool, and programs designed to keep children happily entertained while parents sneak off for spa treatments or quiet beach time. There are bikes all over the property for you to grab and ride, an equestrian center offering horseback riding on the beach, and an extensive menu of water sports. Teens have plenty to keep them engaged too: beach volleyball, kayaking, snorkeling, and enough happening that phones might actually stay in the room. The 400-acre property includes an 18-hole Robert Trent Jones Sr. golf course, world-class spa, multiple pools and tennis courts.. You genuinely never need to leave if you don't want to.

Round Hill takes a quieter, more organic approach to family time. They have a small kids club. What you get is space and flexibility—those private villa pools are perfect for families who want to move through their days on their own schedule. The beach is calm and swimmable, ideal for paddleboarding, snorkeling, or just floating around. Round Hill offers tennis, pickleball, water sports, and a spa, plus they can arrange excursions like catamaran trips or visits to nearby attractions like Dunn's River Falls. The intimate 110-acre property encourages you to slow down and be present with each other.

Both properties also offer cultural experiences that help families connect with Jamaica beyond the resort bubble. Half Moon has Jamaican cooking classes and reggae nights built into the property experience, while Round Hill can arrange more personalized cultural excursions based on your family's interests.

Dining Options

This is another area where each resort's personality really shows.

Half Moon gives you variety. The Sugar Mill Restaurant delivers fine dining in a restored 18th-century sugar mill (the setting alone is worth it), while Seagrape Terrace offers casual beachfront meals. There's also an Italian restaurant, a jerk shack right by the beach, and in-villa dining for those nights when getting kids to a restaurant feels impossible. The range means picky eaters and adventurous foodies can both find their happy place, and you're not eating the same thing every night.

Round Hill focuses on one exceptional restaurant—the Grill—which serves breakfast, lunch, and dinner featuring fresh, locally sourced Caribbean cuisine. The menu changes regularly and the quality is consistently good. While some families might worry about limited options, it rarely feels repetitive. Plus, villa guests have the incredible perk of working with their personal staff to plan custom menus. Your villa chef cooks meals right in your kitchen based on what your family actually wants to eat, which completely changes the vacation dynamic—no negotiations with kids about restaurant behavior, no rushing through meals. Even if you're staying in a Pineapple House room, the Grill's quality means you're not missing out on anything. Added bonus: 4:00pm afternoon tea with sandwiches and sweet treats!

The Vibe Check

Here's what it really comes down to: both Half Moon and Round Hill deliver authentic Jamaican luxury, but the energy is different.

Half Moon feels like a destination unto itself—vibrant, active, with something for everyone at any given moment. It's that resort where you can have a packed day or a lazy one, where kids can choose to have structured activities if you want them, and where you're never wondering what to do next. The variety in accommodations, dining, and activities means it adapts beautifully to different family dynamics and trip styles.

Round Hill is about simplicity and presence. It's intimate, refined, and designed for families who want to exhale and exist together without a packed agenda. The individually designed villas and personalized service create an experience that feels less like a resort stay and more like borrowing a friend's incredibly beautiful Jamaican home—if that friend also happened to employ a private chef and housekeeper.

Planning Your Stay

I loved my time at both properties for different reasons, and I'm confident recommending either depending on what your family needs right now. Want to talk through which one fits your crew? Let's hop on a call or email me. There's nothing I love more than matching families with the perfect property.