Round Hill Hotel and Villas
Hopewell, Montego Bay, Jamaica
Location
Hopewell peninsula, Montego Bay
A 110-acre private peninsula near Montego Bay on the Hopewell coast, a 1950s-glamour address that has drawn Hollywood since 1952 — old-Jamaica elegance around twenty-five to thirty-five minutes from the airport.
Transfer
A short Montego Bay transfer
Around twenty-five to thirty-five minutes by road from Montego Bay's Sangster International, out to the private Hopewell peninsula — a short transfer to a 1950s-glamour world of rooms and staffed villas.
Villas
Rooms & staffed villas
Around 137 in all — thirty-six Ralph Lauren-designed oceanfront Pineapple House rooms and five suites, plus twenty-seven privately owned two- to six-bedroom villas, most with a private pool and each with a dedicated cook and butler, rented when their owners are away — up to the new flagship Villa 14.
Best For
Who it suits
Couples, families and groups — from honeymoons and weddings to multi-generational villa buyouts and executive events — drawn to a private peninsula of Ralph Lauren-designed rooms, staffed two- to six-bedroom villas and old-Jamaica elegance, twenty-five to thirty-five minutes from the airport.
Board Basis
Bed & breakfast
A bed-and-breakfast basis, with the staffed villas offering a private cook — modern Caribbean dining from an on-site organic garden, a casual beach restaurant, a Ralph Lauren-designed bar and the long-standing Monday beach dinner.
Overview
1950s glamour on a private peninsula
Round Hill spreads across a 110-acre private peninsula near Montego Bay, a 1950s-glamour address that has drawn Hollywood since 1952 and where John F. Kennedy and Jackie honeymooned — Ralph Lauren designed the Pineapple House rooms and owns a villa on the estate. Thirty-six oceanfront Pineapple House rooms and five suites pair with twenty-seven privately owned two- to six-bedroom villas, most with a private pool and each with a dedicated cook and butler, privately owned and rented when their owners are away. Executive Chef Martin Maginley cooks modern Caribbean from an on-site organic garden, with a casual beach restaurant, a Ralph Lauren-designed bar and the long-standing Monday beach dinner, while an oceanfront spa of seven treatment rooms, five Har-Tru clay tennis courts and a children's club round out a stay rooted in old-Jamaica elegance. It is around twenty-five to thirty-five minutes from the airport, and a standout for families, weddings and full villa buyouts.
Accommodation
Rooms & staffed villas
Thirty-six Ralph Lauren-designed oceanfront Pineapple House rooms and five suites, plus twenty-seven privately owned two- to six-bedroom villas, most with a private pool and each with a dedicated cook and butler — up to the new flagship Villa 14, in old-Jamaica elegance on a private peninsula.
Entry
Pineapple House Oceanfront Room
Sleeps two, four-poster king. A Ralph Lauren-designed room of around 460 square feet with high ceilings and either fold-back louvered windows or a private patio, with ocean views.
Ralph Lauren designOceanfront
Suite
Pineapple House Suite
Sleeps two, king. One of five suites with a separate sitting area and sea views.
Sea viewOnly five
Villa
Two- to Four-Bedroom Staffed Villa
Sleeps four to eight. A dedicated butler and cook, a private pool on most, and open-air terrace dining with hillside sunset views.
Private cookMost with pool
Group
Five- to Six-Bedroom Staffed Villa
Sleeps up to twelve. Full villa staff, a private pool and larger living and dining space.
Full staffGroups
Signature
Villa 14
Sleeps large groups. The 2024 flagship across a Main House, Tree House and One-Bedroom South, with floor-to-ceiling folding glass and a dedicated staff building.
New flagshipTop villa
Food & Drink
Dining
Executive Chef Martin Maginley cooks modern Caribbean from an on-site organic garden in the main restaurant, with a casual beach restaurant, a Ralph Lauren-designed bar and the long-standing Monday beach dinner — on a bed-and-breakfast basis, with a private cook in the staffed villas.
Fine dining
Main Restaurant
Modern Caribbean by Executive Chef Martin Maginley, from the organic garden.
Beach
Beach Restaurant
A casual beach restaurant, with the Monday beach dinner.
Bar
Ralph Lauren Bar
A Ralph Lauren-designed bar.
Wellbeing
Oceanfront spa
An oceanfront spa of seven treatment rooms sits with an adults-only pool and beach, alongside five Har-Tru clay tennis courts and a children's club and family programme — the quiet, old-Jamaica calm of a 110-acre private peninsula.
Seven treatment rooms
An oceanfront spa of seven treatment rooms, with an adults-only pool.
Five clay courts
Five Har-Tru clay tennis courts, on the peninsula.
Family programme
A children's club and family programme.
Activities & Experiences
Signature Experiences
A 1950s-glamour icon of old-Jamaica elegance — settle into a Ralph Lauren-designed Pineapple House room or a staffed villa with its own cook, dine on modern Caribbean from the organic garden, gather for the long-standing Monday beach dinner, and take the quiet of a 110-acre private peninsula that has drawn Hollywood since 1952.
Ralph Lauren rooms
Ralph Lauren-designed Pineapple House rooms; the designer owns a villa here.
JFK heritage
Where John F. Kennedy and Jackie honeymooned, in 1950s glamour.
Staffed villas
Twenty-seven staffed villas, each with a private cook and butler.
Monday beach dinners
The long-standing Monday beach dinner, a Round Hill tradition.
A private peninsula
A 110-acre private peninsula, drawing Hollywood since 1952.
Getting There
Location & transfers
By road
About 25–35 minutes from MBJ
A short transfer from Sangster International.
By air
Heli from Kingston
Helicopter transfers available.
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Good to Know
Good to know
Board basis
- A bed-and-breakfast basis, with a private cook in the staffed villas.
Heritage
- Hollywood and Kennedy heritage, a 1950s-glamour address since 1952.
Groups
- Staffed two- to six-bedroom villas, for families and full buyouts.
Getting there
- Around twenty-five to thirty-five minutes from Montego Bay's Sangster International.
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Dates & party
Date flexibility
Adults
2
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Budget & accommodation
Budget per person (flights + hotel)
£4,500
£500£50,000+
Villas Preference
Flights
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