A fast growing international villa manager is expanding on the north coast, a sign that Jamaica’s short-term rental market is becoming more professional just as regulation of the sector moves up the agenda.
KINGSTON, Jamaica, 9 October 2026, Bocobay, a London based vacation rental company, has named Jamaica as one of its two main targets for expansion, with plans to manage a new 43 unit oceanfront development in Discovery Bay, St Ann, and to look at more parishes, the Gleaner reported today. The company’s co-founder and chief executive, Nick Curtis, told the newspaper Bocobay could be operating in seven islands within 18 months. For owners of villas and resort apartments, and for anyone weighing a holiday rental purchase, the move points to a market shifting from informal letting towards managed, hotel style operations.
From one villa to 400 homes
Bocobay was founded in 2020 by Mr Curtis and his brother James, starting with a single villa in Aruba during the pandemic. It now manages about 400 homes across Aruba, Curaçao, Jamaica and the Dominican Republic, and says it is tracking around US$50 million in annualised gross booking value. The company says it has doubled in size each year for five years and expects to hire 60 to 80 people over the next 12 months. Rather than charging flat fees, it takes a 25 per cent commission on bookings, which covers management and online marketing.
In Jamaica, the company began a soft launch earlier this year at Palm Beach in Runaway Bay, where it manages 22 villas and six luxury condominiums pitched as a five star product, with villa guests assigned a butler, chef and housekeeper. It is also taking on The Azure in Discovery Bay, a six storey development by KeFordco Ltd that Bocobay plans to run along four star resort lines, with a front desk, permanent staff, a grill, a café and a rooftop bar. According to the Gleaner, more than 30 units are close to ready, and the building is expected to open for the 2026 to 2027 winter season.
A project that took longer than planned
The Azure has been some time in the making. When KeFordco broke ground in April 2022, the Jamaica Observer reported plans for 41 apartments plus penthouses on an acre of oceanfront land at Discovery Bay, an 18 month build and completion by September 2023, with prices starting at US$225,000 for a one bedroom unit. On the current timetable, the first guests would arrive about three years later than that original target. Neither the developer nor Bocobay has publicly set out the reasons for the gap in the reports reviewed for this article. Whatever the cause, it is a reminder to off plan buyers that projected handover dates and projected rental income both carry risk.
Regulation is catching up
The professionalisation of holiday letting arrives as the State looks harder at the sector. In September 2025 the Minister of Tourism said regulating peer to peer accommodation remained on the Government’s agenda, telling a business audience in Montego Bay that more than 30 per cent of the previous year’s visitors had used Airbnb type stays, out of a total the Gleaner put at 4.3 million. Earlier that year, the president of the Jamaica Hotel and Tourist Association told the newspaper that some small hotels in the capital had seen business fall by 30 per cent as apartment buildings were converted to Airbnb style rentals. In May this year, the Gleaner reported that Jamaica was moving to strengthen oversight of short-term rentals through legislation and closer attention to tax compliance, while the Caribbean Hotel and Tourism Association set out a regional framework recommending mandatory registration.
For owners, a professional manager may make compliance simpler, though it does not remove the obligation. An operator that screens guests, handles bookings and staffs a front desk is arguably better placed to meet registration, safety and tax rules than an owner letting a single apartment from abroad. Mr Curtis told the Gleaner the company checks guests’ identification, including those booked through online platforms, and that it cancelled a sizeable booking across a couple of properties last month on those grounds.
What it means for owners and communities
The economics deserve a careful look. A 25 per cent commission is a substantial share of gross income, and owners will need strong occupancy and nightly rates to make the arithmetic work once maintenance, insurance and taxes are counted. For overseas and diaspora buyers who plan to let a north coast property while living abroad, a managed model offers convenience, but it also ties the value of the investment more closely to the fortunes of tourism and to rules that are still being written.
There is a wider question, too. Every apartment that becomes a full time holiday let may be one fewer available to a nurse, a teacher or a young family looking for a long-term rental in the same town. In resort areas such as St Ann, the growth of managed short-term letting will help shape who can afford to live near the coast as well as who visits it.
The outlook
Bocobay’s plans suggest that international operators see Jamaica’s holiday home market as having room to grow, particularly on the north coast. Whether that growth benefits owners and surrounding communities will depend on delivery at sites such as The Azure, on how firmly and fairly the Government regulates the sector, and on whether the expansion of short-term letting is matched by enough new homes for the people who work in the tourism economy.
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