digital nomad Caribbean

Jamaica closed 2025 with record visitor arrivals and an accommodation licensing framework nearing completion, while Barbados refined its STR regime, the EU’s data-sharing rules entered enforcement, and global platforms reported Caribbean as a standout growth market.

New York City’s council voted in January 2023 to enforce its landmark STR registration law, setting a September effective date that would reshape global platform regulation. Jamaica’s H1 2023 tourism arrivals surpassed pre-pandemic records as the unregulated Airbnb sector expanded rapidly, drawing fresh scrutiny from the JTB and Tax Administration Jamaica. Barcelona’s mayoral election pivoted partly on STR reform, and Caribbean digital nomad competition intensified.

Jamaica’s short-term rental market rebounded sharply in the first half of 2022 as tourism recovered faster than expected, the UK government launched the first national STR consultation in January, Airbnb reported 70% revenue growth, Barbados’s Welcome Stamp entered its second year and expanded, and Caribbean inflation began to squeeze host operating costs.

Jamaica’s short-term rental sector began a tentative post-pandemic recovery in the second half of 2021 as vaccination rollout gradually restored international travel confidence. Airbnb completed its first full year as a public company and reported a strong revenue rebound; Caribbean digital nomad visas reshaped accommodation demand; and Jamaica’s hotel sector warned of regulatory disadvantage from an unregulated Airbnb market that was recovering faster than licensed accommodation.

Jamaica’s short-term rental sector navigated a cautious recovery in the first half of 2021 as COVID-19 vaccination campaigns gradually unlocked international travel, the Resilient Corridors tourism model held firm, and digital nomad programmes across the Caribbean began reshaping the accommodation market in ways that Jamaica had yet to capitalise on.

The second half of 2020 produced two events that will define Caribbean tourism and short-term rental markets for years: Jamaica’s pioneering Resilient Corridors reopening model and Airbnb’s landmark IPO, which priced at US$68 and opened trading at US$144 on 10 December 2020, minting a company valued at nearly US$100 billion from the ruins of the year’s pandemic disruption.