Spain Penalizes Airbnb Over Non-Compliance,  Milan To Ban Key Boxes from 2026, Forge Tests AI Assistant

Snigdha Parghan

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Spain Penalizes Airbnb Over Non-Compliance, Milan To Ban Key Boxes from 2026, Forge Tests AI Assistant.
📌TL;DR- Spain has issued a €56M fine against Airbnb for non-compliant listings, signaling tougher enforcement under its new national STR registry. Milan will ban self-check-in key boxes on public property from 2026, adding another layer of local regulation in Italy. Meanwhile, Forge Holiday Group is testing an AI-powered concierge, highlighting how platforms are shifting toward conversational, data-driven travel search.

Airbnb Faces €56M Fine in Spain Over Unlicensed Listings

  • The Spanish government has formally imposed a €56 million fine on Airbnb for listing more than 65,000 unlicensed short-term rentals (STRs), a figure reportedly six times greater than the platform’s estimated earnings from those listings.
  • The fine follows the July 2025 launch of Spain’s national STR registration system, aimed at bringing structure to what had previously been a fragmented, region-by-region approach. 
  • Authorities say Airbnb did not comply, and Consumer Rights Minister Pablo Bustinduy directly criticized the company’s model as one that “expels people from their homes.”
  • Enforcement responsibility is tied to the Consumer Affairs Ministry and housing authorities.
  • Airbnb says it plans to challenge the ruling, claiming it is already working with Spain’s housing ministry to align with the new rules.

Snigdha’s Views

  • Airbnb had already begun working with Spain’s national government months before the fine was issued. Since 2025, it has partnered with the Ministry of Housing to support the rollout of the country’s national STR registry. 
  • The platform says it has helped add registration numbers to more than 70,000 listings since mid-2025 and started removing those with invalid or revoked registrations.
  • From Ibiza, where it’s helping local councils monitor illegal listings, to Murcia, where it’s blocking non-compliant properties, Airbnb has been building credibility region by region. 
  • But while those efforts showed progress, they weren’t fast or thorough enough for Spain’s Consumer Affairs Ministry, which has authority over consumer protections and marketplace compliance. 
  • With the looming Barcelona Ban 2028 and housing protests intensifying, this fine could be the central government’s way of responding to local frustration while also putting pressure on platforms to accelerate enforcement.
  • Professional managers operating in Spain, or even watching from markets like France and Portugal, should be taking this moment to double-check the registration status of every unit, audit how listings are displayed.

Forge Holiday Group Tests AI Assistant ‘Connie’ to Power Natural Language Trip Searches

  • Forge Holiday Group, the company behind major UK rental brands like Sykes Cottages and Forest Holidays, is testing a new AI assistant called Connie the Concierge
  • Announced by Group CEO Graham Donoghue, Connie is designed to help holidaymakers plan and book their UK getaways using natural language, for example, by typing or speaking a request like “I want a quiet seaside cottage that’s dog-friendly.”
  • Built with Microsoft and UK-based data consultancy, Dufrain, the tool uses conversational AI and machine learning to personalise trip searches based on Forge’s internal data, including guest preferences and property characteristics
  • The idea is to move away from filter-heavy, manual browsing toward something more intuitive and human-like.
  • Connie isn’t live for guests yet; it’s currently in internal testing
  • Forge is betting that search and discovery in travel will become increasingly AI-powered, conversational, and personalized. 

About Forge Holiday Group:

Forge Holiday Group is a UK‑based holiday rental company that brings together several accommodation brands, including Sykes Holiday Cottages, Forest Holidays, UKCaravans4Hire, and New Zealand’s Bachcare

The group manages over 30,000 holiday properties and serves more than three million guests annually, offering cottages, cabins, caravans, and other vacation accommodations across a diverse range of locations. 

Rental Scale-Up recommends Pricelabs for Short Term Rental Dynamic Pricing

Snigdha’s Views

  • This isn’t the first time we’ve seen platforms rethink how travellers search. In 2024, Landfolk launched Daisy, a visual tool that lets users search by “feel,” like “seaside escape” or “forest hideaway.” Airbnb is also working on this. 
  • Now, Forge’s Connie takes that a step further, using conversational AI and internal data to create a more natural, human booking experience.
  • It quietly raises the bar on what counts as a “search-ready” listing.
  • For property managers, the shift toward AI-powered search introduces a growing risk: listings with vague titles, weak descriptions, or incomplete amenities could become harder to surface. 
  • While platforms aren’t penalizing this content yet, tools like Connie signal where search is heading and what may soon be required to stay visible.
  • That’s where something like PriceLabs’ Listing Optimizer could come in handy, helping surface which listings might need clearer titles, better descriptions, or more accurate amenities before these gaps start to hurt visibility.

Milan to Ban Self‑Check‑In Key Boxes on Public Property from 2026

  • Starting January 2026, Milan will prohibit the use of self-check-in key boxes placed on public property.
  • This is not a blanket ban on self-check-in: access methods like smart locks or key boxes installed on private property remain permitted, provided they comply with existing guest ID verification requirements.
  • Hosts must remove any key boxes attached to street furniture, fences, light poles, gates, or other structures on public land within 30 days of the rule taking effect, or face fines of €100–€400 plus removal costs.
  • The new regulation follows a city council resolution targeting what authorities see as improper use of public property for private gain. 
  • Florence, Bologna, Rome, and Venice have already enacted similar bans in recent years. 
  • These measures are intended both to maintain urban aesthetics and to address safety concerns tied to unmonitored guest access.
  • The national Ministry of the Interior has argued that in‑person check‑in improves public order and accountability, particularly as STR activity surges around major events such as the 2025 Jubilee.
  • Community groups have actively campaigned against the proliferation of key boxes, seeing them not only as eyesores but as symbols of overtourism and gentrification.

Snigdha’s Views

  • Back in late 2024, Italy’s Ministry of the Interior introduced a nationwide requirement for in-person guest identification, essentially banning remote check-ins like key boxes and smart locks
  • That original ban sparked huge operational headaches, especially for small-scale hosts who relied on key boxes and remote systems to stay efficient. 
  • Then, in May 2025, the Lazio Regional Court overturned the national directive, calling it disproportionate and legally unsound. 
  • Now, with Milan enforcing a new public key box ban for 2026, we’re seeing the issue resurface, but in a more targeted form. This time, the focus is narrower: it’s not about banning all self-check-in, but restricting the use of public space for unmanaged guest access.
  • Even if you’re not operating in Milan, this signals a shift: the mechanics of guest access, how you hand off keys, verify identity, and interact with guests, are now subject to local politics and legal grey zones.
  • Operational workarounds that are legal today may not survive the next municipal vote.