Where To Stay

Round Hill Hotel & Villas

The spirit of Round Hill’s golden age - think 1950s glamour and barefoot elegance - still lingers in the best way. A favorite of celebrities, political icons, and travelers in-the-know, it’s the kind of place people return to when they need to reset and recharge (yes, even Stella would approve). Oceanfront rooms designed by Ralph Lauren channel classic Jamaican charm, while the private villas, each uniquely styled, blend seamlessly into the lush, tropical hillside.

West of Montego Bay

62 Units

20 minutes from MBJ Airport & 25 minutes from Montego Bay

1 Restaurants & 3 Bars

2 Swimming Pools | 5 Tennis Courts | 2 Pickleball Courts | Soccer Field | Glass Boat Tour

The Spa at Round Hill

Pineapple Kids Club | 7up Club

Pascale's Insights

Why

A timeless escape with old-school Caribbean elegance, Ralph Lauren’s favorite resort, where life slows down and every detail feels curated with care
A wide range of privately owned villas, 24 of which feature private pools, and all staffed with cooks and housekeepers, make it ideal for multigenerational families or group getaways.
Classic charm meets refined comfort, expect colonial-style architecture, manicured lawns, and quiet beachfront moments

Now You Know

Ralph Lauren owns a beachfront villa here, and when he’s on island, you might spot him and his family enjoying cocktails at the bar
The resort’s interiors? Many were personally designed by Ralph Lauren himself, adding to the understated glamour
Round Hill was once a favorite hideaway for the Hollywood set, Cary Grant, Grace Kelly, and JFK have all stayed here

Our Two Cents

Don’t miss a walk through the resort’s photo gallery, it’s like a time capsule of Round Hill’s star-studded past
Book a villa for added privacy and that classic villa staff experience, cooked-to-order breakfast on your terrace is a highlight
For a quiet, romantic stay, opt for an Oceanfront Room in the Pineapple House, they’re elegant, serene, and just steps from the sea