Round Hill Hotel and Villas

Round Hill holds a peninsula of about a hundred and ten acres west of Montego Bay, on ground that had been a pineapple and coconut plantation. John Pringle bought it in 1953 and did the opposite of what every other estate in this register did with land: he divided it. Friends and acquaintances were invited to buy a one-acre plot, build a cottage on it, and take a one per cent stake in the profits of the central hotel; the cottage joined the rental pool whenever its owner was away. The subdivision paid for the main house, and the main house made the plots worth having.

Seventy years on the arrangement is unchanged and it is the property. Twenty-six or twenty-seven villas stand on their own acres, divided into seventy-four or eighty-six lettable suites depending on the source, around a seafront block of thirty-six rooms. The owners are still individuals rather than a company. One villa has never entered the pool at all and is simply somebody's house. The hotel operates a gated estate whose freeholds it does not hold, and the beach, the thirty acres of gardens and the paths between them are common ground shared by paying guests and resident owners alike.

Division as the business model. Amanzoe assembled fifty plots into one estate. Round Hill took one estate and sold it as twenty-seven, keeping a share of each. Both produce a world of its own; only one of them funded itself by giving the land away.

A shareholders' hotel. The one per cent stakes mean the villa owners are the hotel's proprietors as well as its neighbours. That is a rung above Jumby Bay's equal shares in an island company: here the share is in the operation, not the ground.

Sources

• Operator history - peninsula of about a hundred and ten acres west of Montego Bay, formerly a pineapple and coconut plantation; John Pringle bought it and opened Round Hill in 1953, inviting buyers to take one-acre plots and build private villas that join the rental pool when the owners are absent
• Independent coverage - each original buyer received a one per cent stake in the profits of the central hotel, which is how the main house was financed; the villas remain individually owned, and one is kept entirely for its owner and never let

Verification

Official source

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Sources disagree

the peninsula is published as a hundred and ten acres and as a hundred; villas as twenty-six and twenty-seven; lettable villa suites as seventy-four and as eighty-six. The thirty-six rooms of the Pineapple House are consistent.

Property confirmation

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Booking

Private Resorts arranges each stay on request, quoting the rates available for the resort and dates. No benefit should be assumed unless it is confirmed in writing for the individual reservation.

Classified by The Resort Collection House · The Register · Edition 2026 · LHL-E-151
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