Caribbean Short-Term Rental & Property Regulation Update: July–December 2025

Six Things to Know

• Jamaica closes 2025 with record visitor arrivals, fuelling STR investment demand
• Ministry of Tourism’s draft accommodation regulations advance to public consultation
• Barbados extends and refines its STR licensing regime for 2026 compliance
• EU Short-Term Rental Regulation enters enforcement phase; platform data obligations tighten
• Airbnb posts record annual global revenue; Caribbean remains fastest-growing region
• PIOJ flags housing affordability pressure in coastal parishes as STR density rises

Jamaica Ends the Year on a Tourism High—but Questions Multiply

Jamaica’s tourism sector closed out 2025 in remarkable shape. Preliminary data from the Jamaica Tourist Board (JTB) indicated that total visitor arrivals for the year surpassed the 2024 record, with stopover arrivals approaching 3.5 million and cruise passenger volumes adding substantially to that total. The north coast resort corridors of Montego Bay, Ocho Rios, and Negril sustained strong year-round occupancy, and the JTB reported that accommodation revenue per available room in licensed properties reached an all-time high.

But the headline numbers obscure a structural tension that has defined Jamaica’s accommodation market for several years. A significant and growing share of the visitor accommodation spend is flowing through unlicensed short-term rental properties listed on platforms including Airbnb, Vrbo, and Booking.com—properties that in many cases are not captured in official occupancy data, do not contribute to the Tourism Enhancement Fund levy, and whose operators may or may not be meeting their income tax and GCT obligations. Estimates circulating within the Ministry of Tourism and the JTB in the latter half of 2025 suggested that Jamaica’s active short-term rental inventory may have exceeded 18,000 units by the end of the year, more than double the number of rooms in licensed hotel and villa properties.

Accommodation Licensing Framework Advances

The most significant regulatory development of the second half of 2025 was the Ministry of Tourism’s release of a draft short-term rental accommodation framework for public consultation in October. The draft, widely anticipated following years of industry lobbying and government signalling, proposed a three-tier licensing structure: an individual host tier for operators renting a single property or unit; a multi-property tier for those operating two to five listings; and a commercial operator tier for those with six or more properties. Each tier would carry different compliance requirements, including safety inspections, insurance obligations, and tax registration conditions.

The consultation period ran through November and attracted submissions from Airbnb, the Jamaica Hotel and Tourist Association (JHTA), the Jamaica Real Estate Board (JREB), and a range of community groups and individual hosts. Airbnb’s submission, the most detailed of the platform responses, broadly welcomed the framework’s principle of proportionality but argued that the compliance burden on individual hosts—particularly requirements for in-person inspections and physical licence display—was disproportionate relative to the income generated by small-scale operators. The JHTA, predictably, pressed for full parity in tax treatment and quality standards between licensed hotels and all vacation rental operators regardless of scale.

Industry observers expect the Ministry to publish a revised framework in early 2026 that reflects at least some of the consultation feedback, with a target implementation date in the second half of the year. Whether that timeline proves realistic given Jamaica’s legislative history on accommodation regulation is an open question—earlier attempts to formalise the STR sector in 2019 and 2022 did not reach the statute book.

Tax Administration Jamaica: Digital Economy Focus Sharpens

Tax Administration Jamaica (TAJ) maintained its focus on digital economy income throughout the second half of 2025, building on the enhanced reporting guidelines it had issued earlier in the year. The agency confirmed in a November press briefing that it was engaging with the OECD’s Model Reporting Rules for Digital Platforms—a framework that obligates platforms to report seller income data to tax authorities—and was exploring how those rules could be adopted under Jamaican domestic legislation. Several Caribbean jurisdictions including Barbados and the Cayman Islands have already implemented OECD-aligned reporting frameworks, creating peer pressure on Jamaica to follow suit.

TAJ also confirmed the rollout of a dedicated digital economy compliance unit that includes short-term rental hosts among its target taxpayer segments. Practitioners report that a number of hosts received compliance letters in Q3 and Q4 2025, particularly in St. James parish, which has the island’s highest concentration of Airbnb listings. Some hosts contacted by TAJ were found to have income above the GCT registration threshold but had not registered, resulting in assessments with interest and penalties.

Caribbean Regional Developments

Across the Caribbean, the regulatory landscape continued to evolve unevenly in the latter half of 2025. Barbados refined its STR licensing framework, which had been in operation since 2023, introducing updated guidance on insurance requirements and a digital portal for licence renewals. The Cayman Islands tourism authority published its first annual STR compliance report, revealing that approximately 40% of the island’s estimated active short-term rental listings remained unlicensed, a finding that prompted renewed calls for enforcement action from the local hotel industry.

The Bahamas, which had previously taken a relatively passive approach to STR oversight, launched a consultation on a proposed registration scheme in August, citing concern about housing affordability in New Providence and Grand Bahama. Trinidad and Tobago, where STR regulation has historically received little legislative attention, saw renewed debate following a high-profile safety incident at an unregistered Airbnb property in Tobago that attracted regional media coverage.

Jamaica’s most direct competitive benchmark remained the Dominican Republic, where the STR market continued to expand rapidly with minimal regulatory friction. The Dominican Republic’s total Airbnb inventory by late 2025 was estimated to exceed 35,000 active listings, dwarfing Jamaica’s market by comparison. Dominican authorities have signalled no immediate intention to introduce a formal licensing regime, arguing that their tourism sector’s scale and diversity makes blanket regulation impractical.

Digital Nomad Programmes: Caribbean Landscape at End-2025

Jamaica’s absence from the global digital nomad visa landscape remained conspicuous at year-end. By the close of 2025, more than 60 countries worldwide had introduced some form of remote worker visa or extended residence scheme designed to attract location-independent professionals. In the Caribbean alone, Barbados, Antigua and Barbuda, Bermuda, the Cayman Islands, Dominica, and Montserrat all had active programmes in various stages of maturity. Jamaica’s repeated expressions of interest in developing a similar product had not translated into formal policy during 2025.

The relevance to Jamaica’s STR market is direct: digital nomad programme participants are among the most frequent and highest-spending long-stay vacation rental guests, typically booking properties for one to three months rather than one to two weeks. Their absence from Jamaica is widely regarded among the STR host community as a lost revenue opportunity, particularly for operators offering larger properties or those willing to offer monthly rates. Renewed calls for a Jamaican digital nomad programme emerged from the private sector during the latter months of 2025, with the JHTA and Jamaica Promotions Corporation (JAMPRO) both understood to be preparing policy briefs for the incoming administration.

International Backdrop: EU Enforcement, Barcelona, and Airbnb’s Record Year

The European Union’s Short-Term Rental Regulation, which had been approved in December 2023 and entered its transitional implementation phase in 2024, moved into fuller enforcement during 2025. The regulation requires platforms operating in EU member states to share standardised host activity data—including number of nights rented, guest counts, and property addresses—with national and local authorities on a quarterly basis. Early reports from EU member states indicated that the data flows were revealing significant discrepancies between platform-reported activity and the numbers of hosts holding formal licences or paying local tourist taxes, fuelling enforcement actions in cities including Amsterdam, Lisbon, and Vienna.

Barcelona continued its phased exit from the tourist apartment model, with the city’s planning department confirming in September 2025 that the first tranche of expiring licences had not been renewed. Property owners and investors in Barcelona’s tourism flat sector accelerated their pivot to long-term residential leases or to sales, with several major portfolios coming to market. Early rental affordability data from the affected neighbourhoods was cautiously positive for long-term tenants, though economists noted the data was still preliminary.

Airbnb closed 2025 with another record financial performance, reporting full-year revenue growth and confirming that the Caribbean region had delivered among the strongest year-on-year metrics of any global geography. The company’s annual host income data, released in December, showed that Jamaican hosts collectively earned an estimated US$180 million in the calendar year—a figure that, while unverified by official Jamaican sources, is broadly consistent with the JTB’s own accommodation revenue data and indicates the material scale of the informal STR economy relative to Jamaica’s formal tourism sector.

Housing Affordability: A Growing Crisis in Coastal Communities

The Planning Institute of Jamaica (PIOJ) drew attention to the STR-housing affordability nexus in its mid-year economic review, noting that in several coastal parishes the proportion of residential properties available for long-term rental had declined measurably over the previous three years as owners shifted to short-term holiday lets. Community organisations in Negril and Ocho Rios submitted representations to the Housing Ministry in 2025 citing specific cases of long-term tenants displaced when their landlords converted properties to Airbnb operations.

The Rent Restriction Act, which dates to 1944 and provides limited and largely unenforced protections for residential tenants, offers no specific provision addressing the conversion of residential properties to tourism accommodation. Legal practitioners have noted that this gap creates significant uncertainty for tenants whose landlords decide to pivot to the STR market mid-tenancy. With a comprehensive tenancy reform bill still not on the parliamentary calendar at year-end, advocates for affordable housing in coastal communities entered 2026 with limited legislative protection and growing urgency.