Hostaway Hits $1B Valuation, Dallas Pushes Rental Ban Ahead of FIFA, San Diego Mulls $5K/Bedroom Tax

Snigdha Parghan

Hostaway Hits $1B Valuation, Dallas Pushes Rental Ban Ahead of FIFA, San Diego Mulls $5K/Bedroom Tax
📌TL;DR- Hostaway just became the first PMS to hit unicorn status with a $1B valuation, setting a new bar for vacation rental software. Meanwhile, Dallas is pushing to enforce its STR ban ahead of the FIFA World Cup, despite legal roadblocks and rising guest demand. In San Diego, a proposed tax of $5K per bedroom on STRs and second homes could squeeze smaller operators.

Hostaway Becomes First Property Management Software to achieve Unicorn status with $1B Valuation

  • Hostaway, the all-in-one vacation rental software platform, has reached unicorn status, becoming the first short-term rental (STR) property management software (PMS) company to achieve a $1 billion valuation.
  • The milestone follows a period of accelerated growth after Hostaway secured a $365 million investment led by General Atlantic in December 2024, which valued the company at $925 million.
  • This unicorn status also aligns with the company’s 10th anniversary.
  • The platform is now used in over 90 countries and was recently named to G2’s list of the world’s 100 fastest-growing software companies.
  • Marcus Rader, CEO and Co-Founder of Hostaway, commented on the milestone: “The first 10 years were about building a product that could reshape the vacation rental industry. Now, it’s about scaling that impact and supporting even more property managers around the world.”

About Hostaway:

Hostaway is a comprehensive vacation rental property management software platform designed to help property managers and owners streamline their operations, grow their portfolios, and enhance guest experiences. Some of the features they offer include channel management, automation tools, and more.

Snigdha’s Views

  • Last year, Marcus Rader told us that their $365M raise signaled that billion-dollar valuations were becoming possible in the ecosystem, like Airbnb’s IPO, and we are seeing that happening now.
  • The company laid the groundwork early, bringing on Cassie Fields as CRO to reach unicorn status, appointing CFO Ashley Milton to steer its growth phase, and naming Ken Weary as COO. Each move pointed to a bigger play, and now it’s materializing.
  • We’ve already seen Hostaway ship a full AI suite recently, like  AI messaging, auto-replies, and more. Hitting this unicorn milestone and marking their 10th anniversary could mean they’ll double down on product rollouts.
  • A billion-dollar PMS has to keep proving its worth, which means more pressure to deliver tools that actually help in growing, not just running operations. That kind of pressure works in favor of property managers.
  • With Hostaway setting a benchmark, other PMS providers will be under pressure to respond, whether that’s by speeding up product updates or prioritizing features that directly improve profitability and ease of use for property managers.

Dallas Wants to Enforce Short-term Rental Ban Ahead of FIFA World Cup

  • The city of Dallas has asked the Texas Supreme Court to lift an injunction currently blocking enforcement of its STR ban.
  • This follows failed attempts at both the district and appellate court levels. Dallas argues that with the city hosting major FIFA World Cup matches next summer, unregulated STRs could lead to disruptions just as global attention descends on the region.
  • The city passed its zoning-based restrictions in 2023, aiming to prohibit STRs in most residential neighborhoods. Operators sued and won a temporary injunction that has held through multiple court rulings. 
  • Meanwhile, the Dallas Short-Term Rental Alliance says it wants to collaborate on reasonable regulation and is already training new hosts to meet demand ahead of the tournament.

Snigdha’s News

Rental Scale-Up recommends Pricelabs for Short Term Rental Dynamic Pricing
  • There’s a real contradiction here. The city is preparing to welcome thousands of guests for FIFA 2026, but is simultaneously pushing to reduce the very accommodation supply that could absorb that demand. 
  • We’ve just seen Airbnb make a similar case in Vancouver, urging local authorities to relax STR rules before the FIFA. 
  • Other cities like Kansas City and Edinburgh in the past have shown a willingness to temporarily flex STR rules during surges in demand.
  • The Dallas STR Alliance seems to be taking the right approach: staying professional, showing a willingness to collaborate, and investing in education.
  • Well-organized advocacy is the only way property managers can hold their ground when high-stakes decisions like this are made.
  • Legal uncertainty remains. Managers in Dallas may have little clarity until the very last moment, a risk for those planning to ramp up for the summer.

San Diego Eyes Up to $5K Per Bedroom Tax on Short-Term Rentals and Second Homes

  • San Diego officials are pushing forward with a proposed “Vacation Home Operations Tax” targeting vacant second homes and full-time STRs. 
  • The draft plan recommends an annual tax of $5,000 per bedroom, potentially impacting 10,000 properties and generating up to $135 million in new revenue. 
  • The goal: discourage speculative homeownership, boost housing supply, and fund essential services.
  • The proposal just passed the City Council’s Rules Committee (3–1 vote) and may appear on the June 2026 ballot
  • Councilmember Sean Elo-Rivera, who introduced the plan, positioned it as a tool to reduce displacement and ensure “vacation property investors pay their fair share.”
  • Opponents, especially small-scale STR hosts, warn that the proposal is overly punitive. They argue it threatens their livelihoods in a city where many rely on rental income to cover the cost of living. 
  • Several voiced concern that they might have to exit the market entirely if this tax is implemented.

Snigdha’s Views

  • San Diego already has  STR rules in place, with strict license tiers, whole-home rental caps, and a one-license-per-host rule. This new tax would add a heavy financial burden on top of that.
  • The $5,000-per-bedroom levy could be enough to displace individual operators, while large investors with deeper pockets might stay put. 
  • The framing is about housing fairness, but in practice, it’s the middle-class hosts who will feel the pinch.
  • Recently, similar tax hikes have been floated in Spain and proposed by Italy’s government.
  • For property managers, this highlights how much can shift through local politics, not just ordinances, but ballot measures. 
  • It also signals that operating in high-demand markets may require navigating not just regulations, but public perception and housing policy debates.