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Judge dismisses StayTerra lawsuits against Stewart, Warren-Kaleta

Written by Leslie Lake on . Posted in Anna Maria Island, Community News.

BRADENTON – The civil lawsuits StayTerra Vacations filed against Kiri Stewart and Jennifer Warren-Kaleta were dismissed on June 18 by 12th Judicial Circuit Judge Charles Sniffen, but the door remains open for StayTerra to amend its original lawsuit complaints.

The original lawsuit complaints filed with the 12th Judicial Circuit Court in Bradenton named StayTerra Vacations, Prime Vacations and GSP Prime Holdings as the plaintiffs. One lawsuit named Stewart and several rental property-related LLCs she is or was associated with as the defendants. One lawsuit named Warren-Kaleta and several rental property-related LLCs she is or was associated with as the defendants. 

It has been noted in court documents and stated during court hearings that Kiri Stewart is the current partner of Shawn Kaleta and Jennifer Warren-Kaleta is Shawn Kaleta’s former wife.

Shawn Kaleta is not named as a defendant in either lawsuit, but his actions and involvement are frequently referenced in the complaints. 

According to the lawsuit complaints, on or around Sept. 18, 2024, GSP, through StayTerra, closed on a transaction with the founders, owners and certain other seller entities to acquire a majority stake in Prime Business. The lawsuit complaints identify Shawn Kaleta and Roman Eckert as the Prime Business owners and founders. The complaints allege a breach of contract for the $105 million consideration StayTerra paid Prime Business in exchange for the exclusive right to collect management fees for the properties for a minimum of seven years. 

According to the lawsuit complaints, the Prime Business owners/founders also agreed to five-year no-compete provisions. The lawsuits allege those no-compete provisions were violated. 

JUDGE’S ORDER

In his written order that granted the defendants’ motion to dismiss, Sniffen stated, “The motion is hereby granted, and the complaint is hereby dismissed without prejudice. Plaintiffs shall have 20 days to amend their complaint in conformity with this order.”

Regarding the legal term “without prejudice,” the Cornell Law School website states, “When a court dismisses a claim but leaves the plaintiff free to bring a subsequent suit based on the same grounds as the dismissed claim.” 

StayTerra representative Elizabeth Chaconas told The Sun on July 1 that StayTerra declined to comment about any possible future legal action. 

In his dismissal order, Sniffen cited multiple issues with the original lawsuit. 

“(It) does not specifically allege whether Kaleta and/or Eckert were signing the agreement as ‘Founders of the Prime Business,’ as authorized signatories on behalf of the individual LLCs that are alleged to own each of the properties, or some combination of both. These allegations shall be clarified in any amendment,” Sniffen’s order states.

“The court rejects the defendants’ argument that the allegations of the complaint, even if accepted as true, fail to state a cause of action for breach of contract based upon an alleged violation of one or more terms of the agreement. The defendants suggest that the allegations of the complaint are insufficient to establish that StayTerra and/or GSP have standing to prosecute breach of contract claims for violation of the agreement in their own names,” the order states. 

The order notes that the plaintiff must prove that the defendants’ conduct “misled guests and distorted the vacation rental market” and “plaintiffs had to mitigate the harm to guests and the public by preventing double-booking and disruption to reservations.” 

The order states, “These short plain statements of ultimate fact do not appear in the complaint and cannot be adequately gleaned from the cited paragraphs.”

In his order, Sniffen stated the 97-page complaint, which included 418 numbered paragraphs, is replete with evidentiary facts and impertinent allegations. 

“The court may strike redundant, immaterial, impertinent or scandalous matter from any pleading at any time. It is hereby ordered that any amended pleading filed in this action shall include only a short, plain statement of the ultimate facts showing that the plaintiffs are entitled to relief and shall avoid the inclusion of unnecessary background details,” Sniffen stated in his order. 

LAWSUITS AND DISMISSALS

The defendants’ motions to dismiss the lawsuits were the subject of a June 4 Zoom hearing conducted by Sniffen. 

Attorney Megan Michalski represented Stewart and Warren-Kaleta at the hearing. Michalski claimed that since Stewart and Warren-Kaleta did not sign the contract with StayTerra, and were not parties to the contract, they cannot be bound by the contract. Michalski also stated the contract does not bar the transfer of rental properties and the self-management of those properties. 

Anthony Paduano, of the New York City-based Paduano and Weintraub law firm, represented the plaintiffs (GSP/StayTerra) during the June 4 hearing. 

“The plaintiffs allege that, in short, they have been swindled,” Paduano said. “Mr. Kaleta is the signatory on the agreement as the agent for the LLCs that are being named as defendants.”

Sniffen later issued his order in favor of Michalski’s legal arguments.

Hearing held for Stewart, Warren-Kaleta, StayTerra motion to dismiss 

Written by Leslie Lake on . Posted in Anna Maria Island, Community News.

BRADENTON – Shawn Kaleta’s alleged actions figured prominently in the discussion that occurred during a June 4 hearing regarding a motion to dismiss two separate but similar civil lawsuits StayTerra Vacations filed against Kiri Stewart and Jennifer Warren-Kaleta in 2025. 

The original lawsuit com plaints filed on Dec. 19, 2025, with the 12th Judicial Circuit Court in Bradenton named StayTerra Vacations, Prime Vacations and GSP Prime Holdings as the plaintiffs. One lawsuit named Stewart and several rental property-related LLCs she is or was associated with as the defendants. One lawsuit named Warren-Kaleta and several rental property-related LLCs she is or was as sociated with as the defendants. Shawn Kaleta is not named as a defendant in either lawsuit, but his actions and involvement are frequently referenced in the complaints. 

According to the complaints, on or around Sept. 18, 2024, GSP, through StayTerra, closed on a transaction with the founders, owners and certain other seller entities to acquire a ma jority stake in Prime Business. The lawsuit complaints identify Shawn Kaleta and Roman Eckert as the Prime Business owners and founders. The complaints allege a breach of contract for the $105 million consideration StayTerra paid Prime Business in exchange for the exclusive right to collect management fees for the properties for a minimum of seven years. 

According to the lawsuit complaints, the Prime Business owners/founders also agreed to five-year no-compete provisions. The lawsuits allege those provisions have been violated. 

According to the complaints, GSP (Garnett Station Partners) is a New York City-based invest ment firm with managed assets of more than $3. 5 billion. 

MOTIONS TO DISMISS 

Circuit Court Judge Charles Sniffen presided over the virtual hearing conducted via Zoom on June 4. The hearing pertained to the motions to dismiss filed on behalf of Stewart and Warren-Kaleta in February. 

During the hearing, the interests of Stewart and Warren-Kaleta were represented by attorney Megan Michalski. 

Michalski claimed that since Stewart and Warren-Kaleta did not sign the contract with StayTerra, and were not parties to the contract, they cannot be bound by the contract. Michalski also stated the contract does not bar the transfer of rental properties and the self-management of those properties. 

“They (Stewart and Warren- Kaleta) are not named in the contract anywhere. The contract promises a revenue stream unless the property is sold or transferred. It specifically says ‘transferred,’” Michalski said. “It also contemplates that if sold or transferred, the new owners can self-manage upon the sale. There is no prohibition against the properties being used as vacation rentals. They allowed the properties to be transferred and self-managed. We ask the complaint to be dismissed.” 

Anthony Paduano, of the New York City-based Paduano and Weintraub law firm, represented the plaintiffs (GSP/StayTerra) during the hearing. 

“The plaintiffs allege that, in short, they have been swindled,” Paduano said. “Mr. Kaleta is the signatory on the agreement as the agent for the LLCs that are being named as defendants. Kiri Stewart is the current partner of Mr. Kaleta and Jennifer Warren- Kaleta is the former wife of Mr. Kaleta. 

“Mr. Kaleta signed as agent for these LLCs and what’s happened is that this transaction is one in which plaintiffs paid $105 million in consideration to Mr. Kaleta as agent in part for the revenue streams over seven years for these LLCs,” Paduano said. 

“We do know that the value that we paid is substantial and it’s not just been compromised, it’s been vaporized from our perspective. Has the agreement been breached? Absolutely. Did Mr. Kaleta sign as manager of these entities? Yes, he sure did. Have we been compensated and paid these revenue streams? No,” Paduano said. 

Paduano alleged some rental properties were transferred to Stewart or Warren-Kaleta to circumvent the StayTerra/Prime Business agreement. 

“The transactions are not bona fide. Some of them are $10 transfers, not legitimate transactions,” he said. “Sometimes the mortgages didn’t move. They remained with the LLCs and the agent is still responsible for them and his personal guarantees. Discovery will prove they’re not proper transfers at all.” 

Sniffen said he would issue a written order on the requested motions to dismiss. 

The next scheduled court hearings are on June 30. 

The two-week nonjury trial period is currently scheduled for August 2027.

Stewart, Warren-Kaleta seek to dismiss StayTerra lawsuits 

Written by Leslie Lake on . Posted in Featured.

 ANNA MARIA ISLAND – Attorneys for Kiri Stewart and Jennifer Warren-Kaleta have asked that the lawsuits filed against them by StayTerra Vacations be dismissed in each of their respective cases. 

The separate lawsuits, both filed on Dec. 19, contain similar allegations of a “deliberate, bad faith scheme” related to a $105 million deal struck with Prime Business in 2024. 

That deal centered around a Property Management Agreement (PMA) made between the lawsuit plaintiffs – Prime Vacations, GSP Prime Holdings and StayTerra Vacations – and the founders and owners of Prime Business. According to the lawsuit complaints filed in December, the founders and owners of Prime Business are Shawn Kaleta and Roman Eckert. 

According to the original lawsuit complaints, the Prime Business owners and founders agreed not to compete with StayTerra for five years; and the founders and owners of Prime Business granted Prime Vacations and GSP Prime Holdings the exclusive right to collect management fees for the properties involved for a minimum of seven years. 

The original lawsuit complaints allege that less than 13 months after entering into the business deal, the defendants “embarked on a deliberate, bad faith scheme to eviscerate the benefit of the bargain plaintiffs struck by facilitating purported transfers of the founders’ membership interest.”

The lawsuits seek not less than $5 million in damages against Stewart and the multiple property-specific LLCs named in her lawsuit; and not less than $9 million in damages against Warren-Kaleta and the multiple property-specific LLCs named in her lawsuit.

Shawn Kaleta is not named as a defendant in either lawsuit, but he is named in Stewart’s lawsuit as her romantic partner and the father of her children. He is also the ex-husband of Jennifer Warren-Kaleta. And he is listed with the Florida Division of Corporations as the manager of several of the LLCs named in the StayTerra lawsuits filed separately against Stewart and Warren-Kaleta.

The motions to dismiss list the St. Petersburg-based Phillips, Hayden & Labbee law firm as the counsel for the defendants.

MOTIONS TO DISMISS

Both motions to dismiss were filed Feb. 23.

In their introductions, both motions to dismiss state, “This is a commercial dispute governed by a written agreement. The problem for plaintiffs (StayTerra) is that the argument they attach does not say what they need it to say. The Master Property Management Agreement (PMA) defines who is bound and what conduct is prohibited. It does not identify the LLC defendants as contracting parties. It does not prohibit the sale of ownership interests. It does not bar self-management. Yet plaintiffs ask this court to recognize those non-existent obligations and hold non-parties liable for breaching them.”

“Unable to find support in the PMA’s text, plaintiffs layer on tortious interference and FDUTPA (Florida Deceptive and Unfair Trade Practices Act) claims built on the same core allegations. But Florida law does not allow litigants to rewrite contracts through creative pleading, convert routine corporate restructuring into tort liability, or transform a private contract dispute into a statutory unfair trade practices case. Because the subject agreement forecloses plaintiffs’ theories and the complaint fails to otherwise plead legally sufficient claims, dismissal of the entire complaint is warranted,” the motions to dismiss state. 

THE ARGUMENTS

The motions to dismiss contain arguments that state the counts pertaining to breach of contract “fail as a matter of law because the PMA does not bind the LLC defendants and no breach is pled.”

The first arguments in each motion to dismiss state, “The PMA identifies the contracting parties and the LLC defendants are not among them. Even assuming the LLC defendants were proper parties, the conduct alleged is expressly permitted by the PMA. Plaintiffs StayTerra and GSP lack standing to assert breach claims because they are not parties to the Master PMA,” the arguments state.

The second arguments in each motion to dismiss state, “Plaintiffs tortious interference claims are legally deficient and cannot survive dismissal.”

The third arguments state, “The FDUTPA/unfair competition claim fails because no deceptive act is identified and the claim is duplicative of the breach of contract claim.”

In conclusion, both motions to dismiss say, “The written PMA controls this dispute – and it does not support plaintiff’s claims. The LLC defendants are not parties to the PMA. The conduct alleged does not breach its terms. The tortious interference counts attempt to impose liability on non-strangers for lawful business decisions. The FDUTPA claim repackages the same contract allegations without identifying a single cognizable deceptive act against a consumer or other party FDUTPA was intended to apply to in the first place.

“Florida law does not permit courts to supply contractual terms that were never negotiated, expand contract disputes into tort liability or convert private commercial disagreements into statutory consumer claims. Because the defects in the complaint are legal, not technical, and cannot be cured without contradicting the agreements plaintiffs rely upon, dismissal with prejudice of the complaint in its entirety is required,” both motions to dismiss state.

(Sun reporter Joe Hendricks contributed to this story.)