Round Hill Resort: My Insider Site Visit in Jamaica

What I loved

• Ease: Being only 25 minutes from MBJ means you can go from the tarmac to a lounge chair in under an hour.

• The villa experience: Having a dedicated staff to prepare fresh breakfast in your villa each morning is the ultimate luxury.

• Tennis culture: It’s no surprise Vogue named it the best tennis hotel in 2024; the facilities are well-appointed and the pros are accessible.

• Aesthetic: Ralph Lauren’s touch creates a sophisticated atmosphere that feels both high-end and residential. The design is also complimented by rituals such as daily afternoon tea service.

Main entrance to Round Hill Resort

Tennis courts with a view of hillside villas

Who should go here

• Round Hill is ideal for families and multi-generational groups, as the villas provide privacy, there is a kids' club, and childcare services are readily available. It is also an excellent fit for social groups or girls' trips looking to share a beautifully appointed villa with dedicated staff. For couples seeking the property's signature romantic atmosphere, I would advise booking outside of spring break periods to ensure a more intimate experience.

Rooms, suites & villas

The property offers 36 guest rooms, five suites, and 27 private villas.

• Rooms: Located in a bi-level building, all 36 rooms are designed by Ralph Lauren and feature ocean views.

• Suites: There are five one-bedroom suites, each with a private entrance and outdoor plunge pool. Note that these suites are not standalone—they are attached to a villa.

• Villas: The 27 villas range from two to six bedrooms and are categorized as Classic (traditional Caribbean decor) or Signature (more modern), and most have private pools. The Estate Villa (Villa 20) is the standout with six bedrooms, two pools, and waterfalls.

View from Oceanview King room

I’m definitely partial to the villas due to the overall experience they provide. All villas include a dedicated staff and a welcome basket of local snacks, beer, and sodas. Breakfast is prepared and served complimentary in-villa each morning. For a fully bespoke stay, guests can pre-order specific groceries at an additional cost, and private chefs are available to prepare lunch and dinner upon request.

Taste of the decor in a villa

Dining

Guests can enjoy à la carte breakfast in the Georgian Grill Room and casual sit-down lunches or themed dinners with nightly entertainment at the Seaside Terrace. For drinks and bites from your lounge chair, there is both a pool bar and beach bar. The Ralph Lauren-appointed cocktail bar is great for a pre-dinner cocktail, and this is also where a traditional afternoon tea is hosted daily.

Ralph Lauren aesthetic in cocktail bar

Beach bar at sunset

Amenities

Beyond the notable racquet facilities, which include four pickleball courts and four tennis courts, guests have access to a full fitness center, yoga pavilion, and jogging trail. The resort also offers plenty of complimentary ways to get on the water, from daily glass-bottom boat tours to kayaking and snorkeling. For families, the daily kids' club and affordable in-villa nanny services at just $15 per hour provide mom and dad with the opportunity to unwind, too.

Beyond Round Hill

Every resort (including Round Hill) is not one-size-fits-all! There are many great properties in Jamaica beyond Round Hill, including GoldenEye, Half Moon, and The Tryall Club. I have a point of view on who to send when and where—contact me to help design the right Jamaican vacation for your needs and desires.

Off-property adventures

If you’re looking to venture off-property, there are several excursion options available, including boat charters (with a pick-up right from the Round Hill dock), river rafting, cliff jumping, and luminous bay tours. There are also a number of dining options worth the drive for a taste of the local cuisine—notable restaurants include House Boat Grill, Marguerites, and Pier 1.

For more inspiration and insider recommendations, visit our Jamaica page.