BRADENTON – StayTerra Vacations has amended the lawsuit complaints originally filed in late 2025 and recently dismissed by Circuit Court Judge Charles Sniffen on June 18.
The original and amended lawsuit complaints name StayTerra Vacations, Prime Vacations and GSP Prime Holdings as the plaintiffs. One of the separate but similar original complaints named Kiri Stewart as the defendant and named as co-defendants several property-specific LLCs Stewart is or was associated with. The other complaint named Jennifer Warren-Kaleta as the defendant and named as co-defendants several property-specific LLCs she is or was associated with.
Warren-Kaleta is developer Shawn Kaleta’s ex-wife. Stewart is his current life partner. Shawn Kaleta is mentioned frequently in the complaints but he is not named as a co-defendant.
In the written dismissal order that granted Stewart and Warren-Kaleta’s motions to dismiss the original complaints, Sniffen stated the plaintiffs had 20 days to amend their complaint in conformity with his order.
According to the complaints, in September 2024, GSP, through StayTerra, closed on a transaction with the Prime Business founders and owners to acquire the majority stake in that business entity. The original complaints identified Shawn Kaleta and Roman Eckert as the Prime Business owners and founders. The complaints alleged 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 Prime Business properties for a minimum of seven years.
According to the lawsuit complaints, Shawn Kaleta and Eckert also agreed to five-year no-compete provisions, which the lawsuits allege have been violated.
As a condition of closing the $105 million transaction, the Prime Business founders and owners entered into a master property rental and management agreement (PMA) with StayTerra Vacations.
In his June 18 order, Sniffen cited multiple issues with the original lawsuit complaints. He stated the similar original complaints filed separately against Stewart and Warren-Kaleta included hundreds of numbered paragraphs that are “replete with evidentiary facts and impertinent allegations.”
In response to Sniffen’s order, each of the amended complaints filed by attorneys Christopher Nigro, John Wagner and Carson Oakley has been shortened. The amended complaint filed against Warren-Kaleta now contains 166 paragraphs. The amended complaint filed against Stewart contains 132 paragraphs.
In his dismissal order, Sniffen stated the original complaints did not specifically allege whether Kaleta or Eckert signed the PMA as the Prime Business founders and owners, or as authorized signatories representing the individual LLCs named in the lawsuit, or some combination of both.
“These allegations shall be clarified in any amendment,” Sniffen’s order states.
With regard to Shawn Kaleta and Eckert’s role as authorized signatories of the PMA, the amended complaints state: “Kaleta and Eckert specifically represented to plaintiffs that they signed the master PMA in September 2024 in their capacity as the owners or legally appointed representatives of the properties that were owned directly by the property owners, and that they were authorized to act on behalf of the property owners.”
Sniffen’s order also notes the plaintiffs must prove that the defendants’ conduct “misled guests and distorted the vacation rental market” and that “plaintiffs had to mitigate the harm to guests and the public by preventing double-booking and disruption to reservations.”
The revised complaints allege, “Defendants diverted bookings and rental revenue from plaintiffs by listing vacation rental properties that were managed by the Prime Business on Airbnb, VRBO and other platforms and then, after receiving a booking for the property, coordinating with the owner of the property to inform plaintiffs that the dates should be blocked off for personal use, a representation that in all instances was false.”
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.
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.)
ANNA MARIA ISLAND – Alleging a “deliberate, bad faith scheme” related to a $105 million deal struck with Prime Business in 2024, StayTerra Vacations has filed a civil lawsuit against Kiri Stewart, Magnolia Cottages LLC and 10 additional LLCs.
Filed on Dec. 19 with the 12th Judicial Circuit Court in Bradenton, the lawsuit names as plaintiffs StayTerra Vacations LLC, Prime Vacations LLC and GSP Prime Holdings LLC.
The lawsuit names as defendants Kiri Stewart, Magnolia Cottages LLC, 48 Street LLC, 9801 Gulf Drive LLC, 224 Chilson Ave. LLC, 243 S. Harbor Dr. LLC, 518 Spring LLC, 2403 Avenue C LLC, 128 Fillmore LLC, 2210 Avenue A LLC, 103 Park Ave. AMI LLC and 6548 Sabal Dr. LLC.
Developer Shawn Kaleta is not named as a defendant, but he’s mentioned in the lawsuit and he’s listed with the Florida Division of Corporations as the manager of five of the 10 property-specific LLCs named as defendants in the lawsuit.
The lawsuit complaint says the plaintiffs, StayTerra, seek “equitable relief to enforce their agreements with the defendant Seller-KS Property Companies (Stewart’s LLCs) and to recover damages to compensate them for the substantial losses they have already incurred as a result of the defendants’ intentional and material breaches of their contractual obligations.”
“By reason of the deceptive and unfair trade practices employed by defendants Stewart and Magnolia Cottages, plaintiffs have suffered damages in excess of $5 million,” the complaint alleges.
“The founders and owners of the Prime Business who bound the defendant, Seller-KS Property Companies, to the Master PMA (Property Management Agreement) were Shawn T. Kaleta and Roman Eckert, the ‘Founders and Owners’. One of the founders and owners of Prime Business is defendant Stewart’s romantic partner and the father of her children,” the complaint says.
“Plaintiffs respectfully requests this court enter judgement in favor of plaintiffs against defendants, award plaintiffs compensable damages in an amount to be proved at trial, but an amount not less than $5 million, in addition to a temporary restraining order, preliminary injunction and permanent injunction prohibiting the defendants from continuing to engage in unfair and deceptive trade practices,” the complaint says.
The case is assigned to Circuit Court Judge Charles Sniffen.
StayTerra is represented by the Sarasota-based Williams Parker Harrison Dietz & Getzen law firm and the New York City-based Paduano & Weintraub law firm.
The lawsuit
According to the lawsuit complaint, GSP is an investment firm founded in or around 2013 with assets under management of more than $3.5 billion.
“Garnett Stations Partners (GSP), through plaintiff, StayTerra and GSP Prime Holdings, paid approximately $105 million to acquire the outstanding equity interests in Prime and other companies comprising a vacation rental management business,” the complaint says.
“In or around late 2023, GSP identified a potential opportunity in the large, growing and highly fragmented vacation rental management industry. Eventually, in or around January 2024, GSP received an introduction to a prominent real estate developer in Southwest Florida who had founded and built a vacation rental management business comprised of six brands (AMI Locals, Anna Maria Island Accommodations, Anna Maria Vacations, Siesta Key Luxury Property Rentals, Lido Key Vacations and Tropical Sands Vacations), referred to herein as the ‘Prime Business,’” the complaint says.
At the time, Prime Business managed approximately 1,110 vacation rental properties, including approximately 130 properties that were indirectly owned or controlled by the founders of Prime Business through the defendant, Seller-KS Property Companies and certain other LLCs, according to the complaint.
“The founder and owners of the Prime Business recognized that they needed liquidity for their real estate development business and also that GSP was an ideal partner to assist with scaling the Prime Business into a national player in the vacation rental management industry,” the complaint says.
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 deal was structured through an Equity Purchase Agreement (EPA) pursuant to which plaintiff StayTerra acquired all of the equity interests in Prime and certain other companies comprising Prime Business for a purchase price of approximately $105 million – consisting of approximately $70 million cash and approximately $35 million in rollover equity in GSP Prime Holdings, the ultimate parent company that owns StayTerra,” the complaint says.
Pursuant to conditions of the EPA, the owners/founders of Prime Business agreed they would not do the following for a period of five years:
Compete with Prime Business (StayTerra)
Recruit or hire any employee, service provider or independent contractor of the Prime Business to leave the employ or cease providing service
Contract with any suppliers of Prime Business
The complaint notes each of the founder/owners of Prime Business entered into a contribution agreement with GSP Prime Holdings in which they agreed to contribute their personal goodwill that included close business relationships with customers and vendors, trade secrets and knowledge.
“As a condition to the closing of the transaction, the founders and owners of the Prime Business delivered a Master Property and Rental and Management Agreement,” the complaint says regarding 10 properties on Anna Maria Island or in Sarasota or Bradenton.
The LLC associated with this vacation rental home at 518 Spring Ave. in Anna Maria is named in the lawsuit. – Manatee County Property Appraiser | Submitted
The LLCs for those 10 properties are listed as defendants. The Florida Division of Corporations lists Stewart as the manager of 224 Chilson Ave. LLC, 48 Street LLC, 9801 Gulf Dr. LLC, 243 South Harbor Dr. LLC and 128 Fillmore LLC. Kaleta is listed as the manager of 518 Spring LLC, 103 Park Ave. AMI LLC, 2403 Avenue C. LLC, 2210 Avenue A LLC and 6548 Sabal Dr. LLC. The Najmy Thompson law firm is named as the registered agent for all 10 of the property-specific LLCs named as defendants.
The Florida Division of Corporations lists Stewart as the manager and registered agent of Magnolia Cottages LLC.
According to the complaint, the founders and owners of Prime Business granted Prime the exclusive right to collect management fees for the properties for a minimum of seven years.
“Yet less than thirteen months after pocketing the consideration comprised of approximately $105 million of cash and rollover equity, 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 in the Seller-KS Property Companies that are subject to the Master PMA to defendant Magnolia Cottages, which is ostensibly owned and controlled by defendant Stewart,” the complaint alleges.
The complaint alleges that in each of the transfer agreements, the founders and owners of the Prime Business, “falsely represented they had the full power to transfer their interests in the Seller-KS Property Companies subject to the Master PMA without obtaining the consent or approval of any other person.”
On Oct. 7, 2025, Stewart and Magnolia Cottages received a cease-and-desist letter from the plaintiffs.
“They were undeterred by that letter and have continued to actively engage in their scheme,” according to the lawsuit.
The complaint alleges, “Defendants Stewart and Magnolia Cottages have assisted the founders and owners of the Prime Business with a ‘shadow listing’ scheme for other properties that indisputably remain subject to the Master PMA.
“Specifically, defendants Stewart and Magnolia Cottages have listed properties that are owned or controlled by the founders of the Prime Business and subject to the Master PMA on Airbnb, VRBO and other booking platforms at prices that are lower than the prices offered by plaintiff Prime,’ the lawsuit further alleges.
Stewart response
On Monday, Jan. 26, Stewart provided The Sun with a written statement that said, “We will vigorously and successfully defend against these claims. The allegations made by Prime are false, misleading and without merit. Prime is a large corporate entity attempting to bully us as homeowners and small property operators by unlawfully seeking control of properties that we own outright.
“Prime previously mismanaged these properties, and we exercised our lawful right as owners to resume control. At no time did we sign away ownership rights or grant Prime authority to possess or control our homes,” Stewart stated.
“Had Prime successfully managed the properties and generated acceptable revenue, we would not have removed them from management. Since self-managing, we have significantly outperformed Prime’s results.
“This lawsuit is a transparent and failed attempt by a Wall Street–backed private equity firm to use the court system to pressure and exploit a small, local business rather than accept responsibility for its own mismanagement,” Stewart stated.
(After this story was published, The Sun learned a similar lawsuit was filed against Jennifer Warren-Kaleta the same day.)
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