Anyone who’s booked a beach house on Florida’s Gulf Coast has probably never thought twice about who actually manages the property behind the listing. A sprawling lawsuit out of Manatee County is a reminder that the answer isn’t always simple, and that a fight over who gets to collect the management fee on more than a thousand vacation rentals can turn into one of the largest civil disputes the local court system has seen.
Thirty-five defendants, two lawsuits, one island
Vacation rental companies StayTerra Vacations LLC, Prime Vacations LLC, and GSP Prime Holdings LLC filed suit against a combined 35 defendants across two separate cases tied to properties on Anna Maria Island and nearby Siesta Key and Lido Key, according to The Anna Maria Islander’s reporting. The cases were filed December 19, 2025, and landed in the 12th Circuit Court, with one case assigned to Judge Charles Sniffen and the other to Judge Stephen Mathew Whyte.
The dispute traces back to a $105 million acquisition in September 2024, when New York-based GSP purchased Prime Business, a company managing roughly 1,110 vacation rental properties along Florida’s Gulf Coast. That purchase agreement came with non-compete and exclusivity clauses running five to seven years, meant to lock in StayTerra’s right to manage those properties and collect the associated fees going forward.
The “shadow listing” allegation
StayTerra’s complaint alleges the defendants ran what it calls a “shadow listing” scheme, completing separate transfer agreements that let them keep collecting rental management fees on properties StayTerra says it holds exclusive rights to under the purchase deal. The company’s filing describes the alleged conduct as “a deliberate, bad faith scheme to eviscerate the benefit of the bargain,” language that signals just how central the exclusivity clause is to the entire case. StayTerra is seeking $5 million in one suit and $9 million in the other, plus attorneys’ fees and an injunction to stop the alleged fee-collection from continuing.
It’s worth being clear about what this case is not. Despite the scale of the dispute and the eye-catching defendant count, there’s no indication in court filings or local reporting that travelers who booked stays at any of these properties experienced cancellations, were displaced, or had trouble checking in. This is, at its core, a commercial dispute between rental management companies over who is contractually entitled to collect fees on the same pool of properties, not a case involving guests losing money or getting stranded mid-vacation.
The defense pushes back
The defendants aren’t conceding the point. According to follow-up reporting from The Anna Maria Islander, they filed motions to dismiss both cases on February 23, 2026, arguing that the written purchase agreement “does not say what they need it to say” regarding what conduct is actually prohibited, and that the agreement doesn’t clearly bind the specific LLC entities named as defendants. As of that reporting, no hearings had been scheduled in either case, meaning the dispute remains in its early procedural stages more than a year after the sale that triggered it.
The individual named in both underlying cases, Shawn T. Kaleta, has separately been party to related litigation in Delaware’s Court of Chancery, according to court records tied to the broader dispute between Kaleta and GSP Prime Holdings, suggesting the fallout from the original $105 million sale has generated legal fights in more than one jurisdiction.
What it means for owners and travelers
For homeowners who list a vacation property through a management company, the case is a useful illustration of how much can hinge on the fine print in a management or acquisition contract. Exclusivity and non-compete clauses are standard in these deals, but enforcing them once a company changes hands, especially across more than a thousand individual properties, is clearly not automatic. For travelers, the practical takeaway is narrower: the company name on your booking confirmation doesn’t always tell you who’s actually running day-to-day operations on the ground, particularly on islands where ownership and management structures have shifted through a wave of consolidation in recent years.
With motions to dismiss pending and no trial date set, the case is likely to stay in the pretrial phase for a while yet. But the sheer number of defendants and the millions of dollars in fees at stake make it one of the more sprawling disputes to come out of Florida’s vacation rental industry recently, and a reminder that behind a single beachfront listing there can be a tangle of corporate ownership most guests never see.
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