This 70-Year-Old Resort in Jamaica Is Steeped in History and Timeless Luxury

It’s difficult not to be giddy during the 20-minute transfer from Sangster International Airport in Montego Bay, Jamaica to the storied Round Hill Hotel and Villas. The 11-mile trip takes you down winding roads abutting the clear blue waters of the Caribbean. As you turn into the hotel itself, giddiness is replaced with an overwhelming sense of calm; my driver (a 40-year veteran of Round Hill), turned to me to simply say, “Welcome home.” 

Round Hill first opened its doors 70 years ago when Jamaican-born entrepreneur John Pringle invited the who’s who of the era to build private cottages on what was once a pineapple plantation. Given the lush, verdant landscape of the surrounding rainforests and the turquoise waters of the bay, it didn’t take long for Adele Astaire, Oscar Hammerstein, and John F. Kennedy to come flocking.

Round Hill has managed to preserve the same sense of old school glamor that pervaded the property in its first few years of operation. Comprising 26 villas (still individually owned by “shareholders”) and the 36-room Pineapple House, which serves as the main hotel area of the resort, the timeless elegance and simple luxury of Round Hill is as beguiling today as ever. 

Villas are available in two-through-six-bedroom floorplans. While each is unique, all feature the same nautical-meets-Caribbean theme (like wooden four-poster beds and tropical flora providing cover for your outdoor shower). Thanks to the indoor-outdoor design, you’ll enjoy a cooling Caribbean breeze from nearly every nook and cranny. All bedrooms feature an en-suite bathroom and terrace, ensuring sanctuary even among larger groups. Many also feature their own private pools, as well as dedicated staff (and private chef) who cater a daily breakfast. The crown jewel of Round Hill — the Estate — is a massive villa at the edge of the tropical rainforest, offering breathtaking views of the ocean below. With two private pools, an open-air living room with both a firepit and a waterfall, and multiple outdoor showers, the Estate is nothing short of a slice of paradise. 

If a villa, however, sounds intimidating, Round Hill also offers beautiful accommodations in the Pineapple House. Designed by Ralph Lauren, the 36-room structure features exclusively oceanfront rooms. Rooms on the second floor boast large jalousie windows that can be folded back to appreciate the views of the Caribbean. Or, opt for a room downstairs, and enjoy your morning coffee from a patio or balcony. 

The charm of Round Hill does not end with its luxury accommodations; the gourmand dining experience includes several options for meals throughout the day. At the Grill – the flagship restaurant – check out Caribbean classics that make use of local ingredients grown on-site at the organic garden; don’t miss the jerk mac and cheese, the farm to table snapper served en papillote, or Scotch Bonnet ice cream. On “Jamaica Night” (or Friday), dine at the Seaside Terrace and try the oxtail or fish escabeche served buffet-style.

Round Hill makes ample use of its naturally stunning setting, with a private beach and watersports that allow guests to take advantage of the beautiful reef that lies just a few yards away from the main dock. There’s complementary snorkeling, paddle boarding, and kayaking, or charter a vessel to take the family waterskiing, tubing, or fishing. Afterwards, relax in the spa, located in the restored Great House of the pineapple plantation. 

Whether it’s small touches like a nightly Jamaican proverb left alongside your bedtime chocolate, or the unbelievably attentive staff throughout the property, there is a distinctive quality to Round Hill that makes coming back easy, and leaving hard. As I pulled away from my first stay at the Hotel, my driver’s departing words to me were, “See you next week.” 

Top Takeaways

Location: Montego Bay, Jamaica 

Rating: Five-Star

The Vibe: Elegant, old-school luxury designed by Ralph Lauren, with classic Caribbean touches throughout

Food + Drink: Check out The Grill at Round Hill, Seaside Terrace, Cocktail Bar, daily Afternoon Tea, and private in-villa dining. Guests can also enjoy light snacks and refreshments on the beach and at the Beach and Pool Bars. 

Amenities: 2300 square foot fitness center; Restaurants; Bars; Spa; Watersports; Tennis; Pickleball; Nightly entertainment; Outdoor swimming pool 

Our Favorite Thing About the Hotel: Every morning, enjoy a complementary cruise to see the local fauna via the glass-bottomed boat. 

What’s Nearby? Appleton Estate; Tryall Golf Club; Dunn’s River Falls & Park; YS Falls; Rose Hall Great House

Rooms: 26 villas and 36-room Pineapple House 

Pricing: Rooms start at $589/night  

Closest Airport: Sangster International Airport

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