Caribbean Short-Term Rental & Property Regulation Update: January–June 2023

Six Things to Know

• NYC Council votes for STR registration law; September 2023 enforcement date set
• Jamaica H1 2023 arrivals surpass pre-pandemic record; Airbnb listings multiply
• Tax Administration Jamaica signals vacation rental income now under active review
• Airbnb Q1 2023 revenue US$1.8 billion, up 20%; Caribbean outperforms global average
• Barcelona mayoral race turns on STR reform; Collboni wins on housing platform
• Caribbean digital nomad visa race intensifies; Jamaica still absent from the field

New York Votes to Enforce: The STR Regulation Era Arrives

The most consequential short-term rental regulatory decision of the year so far did not happen in a Caribbean capital or a European parliament—it happened in New York City in January 2023, when the City Council voted to adopt Local Law 18 and set a September enforcement date that put the world’s most-watched urban Airbnb market on notice. The law, which requires all STR hosts to register with the Mayor’s Office of Special Enforcement and to be physically present during any guest stay, had been under discussion for years and had faced sustained opposition from Airbnb, host advocacy groups, and some members of the hospitality industry who feared that sharply reduced STR supply would damage the visitor economy without materially improving housing affordability for residents.

The council vote was decisive—and Airbnb responded immediately. The company’s CEO Brian Chesky publicly criticised the law as an effective ban on short-term rentals in the city, and Airbnb’s public affairs team engaged in an aggressive lobbying effort to delay or modify implementation. A legal challenge filed by Airbnb and a coalition of hosts was dismissed by the federal courts in the months that followed, clearing the path for the September 5 enforcement date.

The New York City vote was closely followed by policymakers in Jamaica and across the Caribbean, not because any Caribbean jurisdiction was contemplating similar enforcement—but because it demonstrated conclusively that major democratic governments were willing to impose significant costs on platforms and their hosts in pursuit of housing policy goals. The balance between visitor accommodation needs and residential affordability, between tourism revenue and community character, was no longer a theoretical debate. In New York, it had become law.

Jamaica: A Booming Season, a Widening Gap

Jamaica’s tourism sector continued its strong post-pandemic recovery in the first half of 2023. JTB data indicated that stopover arrivals for the January-to-June period had exceeded 1.7 million—a new H1 record that surpassed the comparable figures for both 2019 and 2022. Hotel occupancy rates in the major resort areas of Montego Bay, Ocho Rios, and Negril were running above 70% for the first six months, and air passenger numbers through Sangster International Airport set new monthly records in both January and March.

Within that strong tourism performance, the short-term rental sector was growing faster than the licensed accommodation sector. Airbnb’s Jamaican listing inventory was estimated to have grown by approximately 15% over the previous twelve months, driven by a combination of new property owners entering the platform, existing hotels and villas diversifying their distribution onto Airbnb, and returning diaspora investors converting family properties for short-term rental income. The platform’s Jamaica community now numbers in the tens of thousands of active hosts, concentrated in St. James and St. Ann but with a growing presence in parishes traditionally less associated with tourism, including Portland, St. Mary, and the Blue Mountains corridor.

The regulatory gap between licensed and unlicensed accommodation remained stark. A licensed hotel operator in Montego Bay paying room tax, GCT, and Tourism Enhancement Fund levies, passing regular health and safety inspections, and complying with employment law faces a substantially higher cost structure than a neighbouring Airbnb property owner with no licensing obligations and limited tax exposure. The JHTA has characterised this as a structural competitive disadvantage and has renewed its calls—issued with increasing urgency since 2019—for the Ministry of Tourism to produce a formal STR regulatory framework before the end of 2023.

Tax Administration Jamaica: Vacation Rental Income in Scope

Tax Administration Jamaica signalled during the first half of 2023 that income earned from short-term vacation rentals—whether listed through digital platforms or rented informally to tourists—is within the scope of Jamaica’s existing income tax and GCT framework and should be reported accordingly. The signal came not through formal new guidance but through a series of outreach activities and conference presentations in which TAJ officials noted that the digital economy was a priority compliance focus and that accommodation income was explicitly included.

TAJ has not yet published dedicated STR guidance or commenced a formal campaign targeting vacation rental hosts, but practitioners working with Jamaica’s property and tourism sectors report that the agency’s awareness of the scale of undeclared STR income is growing. The OECD’s Model Reporting Rules for Digital Platforms—which provide a framework for tax authorities to receive income data directly from platforms such as Airbnb—have been shared with TAJ through the Caribbean-OECD tax policy dialogue, and the agency is understood to be considering whether Jamaica has the domestic legislative authority to compel such reporting or whether new regulations would be required.

Airbnb’s Financial Recovery Continues

Airbnb’s first-quarter 2023 financial results, released in May, reported revenue of US$1.8 billion—a 20% increase on Q1 2022. The results confirmed that the company’s recovery from the pandemic was complete and that growth momentum remained strong across its major markets. The Caribbean featured prominently in the platform’s commentary on growth markets, with the region credited as one of the strongest-performing geographies by both nights booked growth and average daily rate.

The company also reported in its H1 communications that it had more than 7 million active listings globally as of mid-2023, up from approximately 6 million a year earlier—growth that was driven disproportionately by international markets rather than the established North American and Western European inventory where listing growth has slowed. Jamaica’s contribution to that global inventory growth, while not broken out separately in Airbnb’s public disclosures, is understood by JTB market researchers to be material at the Caribbean regional level.

Barcelona’s Election and the European STR Mood

Barcelona’s June 2023 municipal elections provided the most dramatic European illustration of how short-term rental regulation has become a mainstream political issue. Jaume Collboni of the Socialist Party won the mayoralty on a platform that included ambitious commitments on housing affordability, explicitly targeting the city’s concentrated tourist apartment sector as a contributor to rental price inflation that was pricing residents out of central neighbourhoods. Collboni’s victory—in a city that already had among the most restrictive STR regimes in Europe—signalled that even in jurisdictions with existing controls, political pressure for further tightening was building rather than abating.

The broader European mood on STR regulation was similarly directional. The EU Commission’s draft regulation on short-term accommodation data-sharing was advancing through the legislative process, with a final vote expected in late 2023. Amsterdam had further reduced the number of nights per year an entire home could be rented on platforms from 60 to 30. Portugal had announced a review of its “Golden Visa” programme that had incentivised foreign property investment in STR-intensive coastal areas. The common thread—that platform-driven tourist accommodation requires active management rather than passive permissiveness—was gaining political traction across the European Union in ways that were beginning to reach Caribbean policymakers through regional hotel association networks.

The Caribbean Digital Nomad Race

Jamaica’s absence from the Caribbean digital nomad visa landscape remained a recurring theme in regional tourism and investment commentary during the first half of 2023. Barbados’s Welcome Stamp, launched in July 2020, had by mid-2023 attracted thousands of remote workers and their families for stays of between three months and one year, generating sustained demand for the island’s villa and STR property inventory. Antigua and Barbuda’s Nomad Digital Residence programme, Bermuda’s Work from Bermuda certificate, the Cayman Islands’ Global Citizen Concierge Programme, and Montserrat’s Remote Worker Stamp had collectively positioned the English-speaking Caribbean as the most diverse and accessible digital nomad destination in the world.

Jamaica’s absence from this competitive landscape was not for lack of awareness. The JHTA and JAMPRO had both produced policy briefs on digital nomad visa programmes by 2022, and the topic had been raised in parliamentary questions and in media commentary. But no formal programme had been announced as of mid-2023, and the practical barriers—including Jamaica’s relatively high cost of living compared to some regional competitors, concerns about crime perception, and the administrative requirements of creating a new visa category—had so far prevented the island from capturing what STR host communities describe as one of the highest-value and lowest-impact categories of visitor in the Caribbean market.