Luxury Hotels Atlas / Places / Jamaica / Hopewell / Round Hill Hotel and Villas
Round Hill Hotel and Villas
Hopewell, Saint James, Jamaica · Independent · Core Luxury
John F. Kennedy and Jacqueline Kennedy honeymooned in Villa 10 at this 1953 resort that Jamaican John Pringle founded on a former pineapple and sugar plantation on a private peninsula near Montego Bay. Ralph Lauren personally redesigned the 36 rooms of the Pineapple House hotel block, on 110 acres with 27 villas designed by architect William Ballard.
- 27 rooms
- Opened 1953
- Neighborhood: Cornwall County
- Rooms from 460 sq ft (43 m²)
- Architect: William Ballard
- Interiors: Ralph Lauren (Pineapple House)
About Round Hill Hotel and Villas
- The '& Villas' name was formalized in 1997, more than forty years after John Pringle opened the peninsula.
- AAA Four Diamond and MICHELIN One Key as of 2025.
- Entry-level rooms start at 460 sq ft (43 m²).
History
Round Hill Hotel and Villas opened in 1953 on a former pineapple and sugar plantation on a private peninsula near Montego Bay, Jamaica, founded by Jamaican John Pringle. Its Pineapple House hotel block and a scattering of privately owned villas set the template for a discreet, glamorous Caribbean retreat, drawing figures such as John F. Kennedy and Jacqueline Kennedy, who honeymooned in Villa 10.
The '& Villas' identity was formalised in 1997, and the Pineapple House's 36 rooms were later redesigned by Ralph Lauren. Set on 110 acres with 27 villas, the independent resort remains one of Jamaica's storied old-money hideaways.
Restaurants and bars
- Pineapple House cocktail lounge — Bar
Experiences
- See, Touch and Taste Program — Guests pick vegetables from the on-property garden, which the chef prepares for their next meal.
- Coral gardening reef restoration with Seascape Caribbean — Corals are grown in a nursery and replanted on the house reef, with local fishermen trained as Coral Gardeners.
- Kids clubs (Pineapple Kids Club and 7-Up Club) — Programming includes Glass Bottom Boat excursions, nature walks, beach Olympics, jewelry making, and movie nights.
- Off-property tours — Historic Great House tours, river-rafting, horseback riding and ziplining in Montego Bay and surrounding areas, arranged by the hotel.
- Complimentary fitness and yoga classes, pickleball and tennis — Guests can use the fitness center, play pickleball or tennis, or join complimentary fitness and yoga classes.
Amenities
- Spa
- Pool
- Hot tub
- Fitness center
- Tennis
- Kids club
- Butler service
Awards
- Forbes Travel Guide Recommended (2026)
- MICHELIN One Key (2026)
- AAA Four Diamond (2025)
Open Round Hill Hotel and Villas in the atlas for live weekend rates, photos, and the full folio.