Round Hill Hotel And Villas
Montego Bay, Jamaica
Book the Pineapple House if you're a couple—these Ralph Lauren-designed rooms sit right above the infinity pool with ocean views, so you can skip the golf cart rides and walk to everything while still feeling like you're in your own private sanctuary.
Established in 1953 on Jamaica's picturesque coastline, this historic resort has welcomed luminaries like John F. Kennedy and Paul McCartney. Set on a private 110-acre peninsula near Montego Bay, it has preserved its heritage while offering luxurious amenities.
Those seeking an intimate Caribbean escape with personalized service will appreciate the resort's commitment to authentic Jamaican experiences.
Rooms and suites
Accommodations include oceanfront rooms designed by Ralph Lauren, featuring elegant furnishings, deep soaking tubs and freestanding rain showers. Floor-to-ceiling windows open to balconies or patios with sea views. Couples seeking a romantic getaway will enjoy these rooms.
For families and groups preferring privacy and ample space, villas ranging from two to six bedrooms provide open-air living spaces, climate-controlled bedrooms and private pools. Each villa comes with dedicated staff, including butlers and personal chefs who prepare made-to-order breakfasts, enhancing the personalized experience.
Amenities and experiences
The Seaside Terrace, the Georgian Room and the resort's bars offer ocean views with menus featuring local and international cuisine.
Spa treatments using local botanicals in a restored plantation house; modern fitness center and yoga sessions in an open-air pavilion overlooking the sea.
Complimentary snorkeling, kayaking and paddleboarding; additional options include water skiing, tubing, scuba diving and private catamaran cruises for snorkeling or sunset sails.
Five tennis courts — clay and hard surfaces, some lit for night play — and pickleball courts with equipment.
The Pineapple Kids Club and 7-Up Club with activities such as reggae dance lessons, nature walks and arts and crafts.
Heritage tours, afternoon tea at the Cocktail Bar and live entertainment with local bands and traditional music.
How to get here
Located 25 minutes by car from Sangster International Airport (MBJ) in Montego Bay, the resort provides private transfers and car rentals. Though secluded on its private peninsula, it is close to attractions such as the historic Rose Hall Great House and the vibrant Hip Strip.
