Last Updated on October 29, 2025 by Dorothy Smith
The couple sitting across from me at the little café on Vine Street looked exhausted, and not just from the Florida heat. They’d just come from a presentation at their resort on West Irlo Bronson, where they’d been told, for the third year in a row, that their time share was an “appreciating asset.” They knew it wasn’t. You could see the weight of it on them. That was back in 2018, I think, right before the tourism boom really kicked off again. It’s a look I’ve come to know well living here.
Honestly, the time share landscape in Kissimmee is its own unique beast. We’re not Orlando, with all its corporate gloss. We’re the heart of the family vacation zone, surrounded by all those resorts along the 192 and in places like Celebration. That means a huge concentration of time share properties, and with that, a huge number of owners who eventually realize it’s not the dream they were sold. The sheer volume of it creates a specific set of challenges—and opportunities for lessthanreputable outfits to swoop in. I’ve been navigating this specific world for over a decade now, helping folks from Buenaventura Lakes to downtown Kissimmee untangle themselves.
What Time Share Exit Really Looks Like Around Here
Most people who call me have the same initial thought: “Can’t I just sell it?” To tell you the truth, that’s the biggest misconception. The resale market for time shares in the Kissimmee area is flooded. I mean, absolutely saturated. You’ll see them listed for a dollar on eBay, and sometimes they don’t even sell. The developers have that primary sales market on lock, and they’ve structured things so the resale value plummets. It’s a tough pill to swallow for a lot of families who sunk their savings into this.
So, the real work isn’t sales; it’s cancellation. It’s about finding a legitimate, legal path out of the contract. And that’s where you have to be careful. We have our fair share of “exit companies” that pop up, make big promises, take a huge upfront fee, and then vanish. I’ve had to help clients clean up that mess, and it stings. That one still gets me frustrated.
The local challenge, funny enough, is partly the weather. Seriously. Hurricane season makes everything bureaucratic move slower. If you’re trying to get documents notarized or filed with the Osceola County Clerk’s office and a storm is brewing, everything grinds to a halt. It adds another layer of patience you need to have with the process.
The Insider’s View on Your Options
Okay, so let’s break down what actually works. There are generally three paths I see for Kissimmee folks, and the right one depends entirely on your specific contract and developer.
1. The Deedback or Surrender Program
Some developers—not all, but a growing number—have started offering programs where you can simply give the time share back to them. They might call it a “surrender” or “deedback.” Now, wait—actually, let me rephrase that more clearly: they might offer this, but they won’t advertise it. You often have to be in default on your maintenance fees to even be considered, and even then, it’s a negotiation. It’s not a great feeling to let those fees lapse, but sometimes it’s the only lever you have. I helped a retired couple from the Kissimmee Lakefront area do this a few years back. It was stressful for them, but in the end, they walked away clean without a huge financial hit.
2. The Resale Route (With a Heavy Dose of Reality)
I don’t want to say selling is impossible, but it’s close. If you do go this route, you need to understand the numbers. A week you paid $20,000 for might sell for a few hundred, if you’re lucky. And the closing costs might be more than the sale price. The only time I’ve seen a semisuccessful resale recently was for a very specific, highdemand week at a toptier resort near Reunion. And even then, it took over two years. The key is to never, ever pay an upfront listing fee. Legitimate brokers work on commission from the sale.
3. The Legal Cancellation Path
This is where the real expertise comes in. This involves a lawyer reviewing your contract from top to bottom looking for what we call an “out.” It could be a technicality in how the contract was signed, a violation of Florida’s time share laws, or misrepresentation by the salesperson. Florida has some of the most detailed time share statutes in the country, believe it or not. A good attorney knows how to use them. This isn’t about suing anyone; it’s about using the law to negotiate a release. This is the path that works for most of my clients who have a strong case.
What This Actually Costs in Osceola County
Pricing is all over the place, which is why people get confused. Let me give it to you straight.
Most homeowners in the Kissimmee area who go the legal route spend somewhere between $4,500 and $9,000 in total legal fees. It sounds like a lot, but you have to weigh it against a lifetime of maintenance fees that can run $1,000 to $2,000 a year—and they only go up. I’ve made the mistake myself early on of underestimating how complex some of these cases can be, so I know how that initial quote can shock people. But when you do the math over 10 or 20 years, it almost always makes financial sense to get out.
And for heaven’s sake, if a company asks for more than $10,000 upfront, run. Just run. Those are the outfits that give this industry a black eye.
Local Providers You Can Actually Talk To
Based on actual local presence and my dealings in this industry, here are some established legal providers that have handled time share exits for folks in Central Florida. This isn’t an exhaustive list, but it’s a starting point based on what I’ve seen.
Lindsey Cancellation — Serves the greater Kissimmee and Orlando area.
Maslack Law Firm — Based in Florida with extensive time share experience.
Larson Lawyers — A Florida firm familiar with statespecific time share laws.
Anyway, the point is to do your homework. Check them out with the Florida Bar Association to make sure they’re in good standing. It’s the single most important step you can take.
Navigating the Rules and Red Tape
Florida doesn’t play around with time shares. The Florida Department of Agriculture and Consumer Services actually has a whole division that handles complaints related to time share sales. It’s one of the few states that does. And if you’re dealing with any kind of exit company, you need to verify they’re properly registered. The amount of paperwork can be daunting, but it’s your shield against scams.
You know what’s funny? I had a client from the Mill Run area who kept every single piece of paper from his original purchase in 2005—the sales brochures, the notes he scribbled, everything. That box of paperwork ended up being the key to his cancellation because it proved a specific claim the salesperson made was false. So my counterintuitive tip? Don’t throw anything away. Not yet.
Questions I Hear All the Time in Kissimmee
Can I just stop paying my maintenance fees?
You can, but it’s risky. The developer can foreclose on the time share, and in Florida, they can sometimes go after your other assets for the debt and ruin your credit. It’s not a clean break and should only be considered as a last resort or as part of a negotiated strategy with a lawyer.
Will the developer just let me out if I ask?
Almost never. Their entire business model relies on the perpetual stream of maintenance fees. They have no incentive to let you go willingly. But a strongly worded legal letter citing Florida statutes? That gets their attention.
How long does the whole process take?
From start to finish, a typical cancellation takes anywhere from 6 to 12 months. There’s a lot of backandforth, waiting for responses, and filing paperwork. You have to be patient. The ones that promise “90 days or less” are usually selling you a fantasy.
Are there any legit companies that help with this?
Yes, but the legitimate ones are almost always law firms or are backed by attorneys. They don’t use highpressure sales tactics, they’re transparent about fees, and they never guarantee a specific outcome upfront. If it sounds too good to be true on the phone, it almost certainly is.
So, if you’re in Kissimmee and that time share feels like an anchor, start by gathering all your documents—the contract, the payment history, everything. Then, have a calm, measured conversation with a Floridalicensed attorney who knows this specific world. It’s the first step toward getting your peace of mind back, and around here, that’s worth more than any vacation package.