You expected passive income, not constant headaches.
But if you own a home in Windsor Island Resort, there’s a good chance you’ve felt the sting of slow responses, hidden fees, or disappointing guest reviews despite paying top dollar for “management.”
You’re not alone. Many homeowners start with big-brand or budget property managers, only to find themselves doing the follow-ups, solving guest issues, and cleaning up poor communication.
This blog isn’t fluff. It’s the real reasons why Windsor Island owners are switching to FunStay and what makes the difference between frustration and five-star freedom.
Let’s talk about what’s going wrong and what you can do about it.
Top Reasons Owners Leave Their Current PM (Property Managers) at Windsor Island Resort
Managing a short-term rental shouldn’t feel like a full-time job, especially when you’ve already hired someone to do it. But if you’ve been with one of the big-box or out-of-town property managers at Windsor Island, these frustrations might hit close to home:
“They never respond.”
One of the most common Airbnb manager complaints at Windsor Island Resort? Radio silence. Owners are left waiting days for answers, while guests are stuck figuring things out on their own. And let’s be honest, slow replies equal bad reviews.
“There are hidden fees everywhere.”
You thought you were paying a flat rate until the monthly report comes in, and you’re staring at line items you’ve never heard of. Late-night lockout fee? $75. Restocking fee? $40. And let’s not even talk about the 20%+ commission that doesn’t include cleaning.
“Guests are leaving bad reviews.”
Poor cleaning, clunky check-ins, and maintenance delays? They all show up in your guest feedback. And once the reviews start sliding, so do your bookings. This is how the worst property management at Windsor Island slowly chips away at your income.
“There’s no transparency.”
You deserve to know what’s going on with your investment. Instead, some PMs give you generic reports with no context, no breakdown of nightly rates, and no strategy behind your pricing.
“They’re not even local.”
How can someone manage a guest emergency from another city? Out-of-town teams and corporate managers lack the local insight (and availability) to solve problems fast, and it shows.
What Owners Actually Want in a Property Manager
After the missed calls, surprise charges, and guest complaints, you start to realize what really matters in a property manager.
It’s not just someone who can book a stay. It’s someone who actually shows up when it counts.
What Windsor Island homeowners really want is simple:
- Responsive, local support — not a call center across the country
- Guest reviews that rave about “clean,” “easy,” and “fast check-in”
- Clear pricing and transparent revenue reports—no “gotcha” fees
- Personalized service that adapts to your property and goals
- A best-rated property manager in Windsor Island Resort who’s actually been a host, knows the platform inside and out, and treats your home like it matters
And when all of that comes together? You get peace of mind, better reviews, and stronger bookings without the constant second-guessing.
How FunStay Solves What Other PMs Don’t
When Windsor Island owners come to us, they’re not just looking for help—they’re looking for relief.
Here’s why so many switch to FunStay (and wish they’d done it sooner):
| ✅ What You Get with FunStay | ❌ What You’re Getting Now |
| ✅ Real Local Support | ❌ Corporate Gaps & Delays |
| Superhost-owned & operated by a licensed Florida Realtor | Offshore reps or call centers who’ve never seen your home |
| Based near Windsor Island — available 24/7 | Long hold times or no-show maintenance teams |
| We know your HOA rules, community quirks, and guest expectations | Blanket policies that don’t fit Windsor Island rentals |
| ✅ Results You Can See | ❌ Guesswork & Missed Potential |
| Higher guest ratings: “clean,” “easy check-in,” “amazing host” | Reviews with complaints about check-in, broken items, or poor support |
| Real owner testimonials showing revenue growth | Vague reports and no proof of pricing optimization |
| Smart pricing + SEO listings = more bookings & better reviews | Static pricing, outdated photos, no real strategy |
| ✅ No Guesswork. No Gimmicks. | ❌ Fees & Frustration |
| Flat-rate pricing — no surprise deductions or admin fees | Cleaning markups, hidden service fees, and confusing payout breakdowns |
| Direct access to your manager (text/call anytime) | No transparency, rotating reps, no accountability |
| Real-time updates, clean reports, peace of mind | Radio silence unless there’s a problem |
This is why Windsor Island owners switch and stay with FunStay.
Owner Stories: Why They Switched to FunStay
★★★★★
Donna R.
For anybody who purchased their property(ies) as a short term rental… If you are NOT satisfied with the number of bookings (and the income you have been getting from your management company) please pay attention to this post. My fiance and I had given up hope that we would ever get bookings (even though we had set our property up with everything possible and furnished it with all new items) because after six months, we had only gotten TWO bookings. We took a chance on a recommendation to switch to FunStay Vacation Homes, and all I can say is WOW!!! Within a matter of DAYS, not only did we get our first few bookings, but they have entirely booked up the next five weeks for us. They are super friendly, professional, easy to work with and all I can say is THANK YOU!! We now have renewed hope that this short term rental will pay for itself (monthly expenses), and very shortly down the road, be an income generator for us.
★★★★★
Phil C.
Since switching to FunStay Homes for property management, my rental income has increased by 40%. What really sets them apart is their responsiveness, personalized service, better guest reviews, and top-notch marketing. In addition FunStay supports owners with guest issues and saves me from dealing with bad guests and has saved me considerable time and money. I couldn’t be happier.
★★★★★
Yezi O.
We’ve been using FunStay Homes to manage our three vacation properties for over a year now, and the difference has been incredible. Our previous management company was unresponsive and failed to bring in quality bookings. Since switching to Mike and his team, we’ve seen a major improvement in both occupancy and revenue. The communication is excellent, guest satisfaction has gone up, and our homes are better maintained than ever before. Mike truly understands the needs of property owners and treats our homes with care and professionalism. Choosing FunStay Homes was one of the best decisions we’ve made.
★★★★★
Sarah T.
We’ve owned vacation rentals for over a decade, and the team at FunStay Homes has completely transformed how we manage our properties. Since Mike took over, our bookings have increased.
What Guests Are Saying
★★★★★
Jaygi C.
I had such a great experience with FunStay Homes! The place was clean, cozy, and had everything I needed to feel comfortable. The check-in process was super easy, and the location was perfect & close to shops and restaurants but still peaceful. I really appreciated the great communication and how welcoming everything felt. Highly recommend if you’re looking for a reliable and beautiful place to stay!
★★★★★
Yenni F.
I had an absolutely wonderful time with my family, The place was spotless, beautifully decorated, and had everything I needed to feel comfortable and at home. The bed was super cozy. The location was perfect, close to everything, safe neighborhood. Communication with the host was smooth and quick. Adam was incredibly friendly and helpful. Highly recommend FunStay, I would definitely book again!
★★★★★
James R.
We stayed in one of FunStay Homes’ cabins and it was absolutely magical. Very private, peaceful, and perfect for our two Labradors. The cabin had thoughtful features like a gated porch and beautiful rustic decor. We especially loved the high ceilings and quirky art downstairs.
★★★★★
Benjamin G.
This home was absolutely perfect for my family and me! It was beautiful, comfortable, and had everything we needed for a wonderful stay in Florida. The host was incredibly welcoming and made the experience even better. Highly recommend for anyone looking for the perfect place to stay!
★★★★★
Joe D.
Absolutely loved the place! It was exactly what we needed for our stay! Super close to Disney, and shopping centers. The pool, game room, and grill were a excellent experience. Everything was clean and well taken care of. The entire staff were very friendly and helpful. Will 100% book again!!!
★★★★★
Angel B.
I found them on Facebook and booked directly on their website and got an amazing discount! No regrets at all. The place I booked was clean and beautiful aand truly awesome tbh! 🙂
★★★★★
Annie C.
We had a wonderful stay with FunStay Homes in Orlando! Mike is the best host any guest could ask for!
★★★★★
Maria G.
I love all the accommodations Mike had for children; play pen, high chairs, life vest (all sizes). Would definitely consider staying here again! Thanks so much for making my kids first Disney trip that much more memorable!
★★★★★
Dayna C.
The cabin was private, quiet and peaceful! We felt like we were in a tree house! It was perfect for us and our pups. We enjoyed many of the amenities in the cabin and the wrap around porch (which has a gate, great so the pups could be with us). The sunsets were beautiful. The cabin looks like the pictures and the description in the listing. The lower level has the most amazing high ceilings and fun artwork. So much to love about the cabin. The hosts were great and very responsive. We go to the mountains 1-2 times a year and we would definitely stay here again. A Wonderful Smoky Mountain Vacation!!!
★★★★★
Daniel G.
Mike was very responsive and kind. Helpful with recommendations on fun activities for the family. The property was very clean and decorated with fun pictures and props, the kids loved it. Would recommend and planning on staying again. The water park and amenities with the resort were a big hit.
Your Next Move
You don’t have to stay stuck with a property manager who’s dropping the ball. Whether you’re dealing with guest complaints, confusing payouts, or just feeling left in the dark, we’re here to change that.
At FunStay, we’re local, we’re accountable, and we’re ready to earn your trust the way your last manager didn’t.
Let’s take a look at your Windsor Island rental, run the numbers, and see what’s really possible.
—let’s fix what’s not working.
📞 Call/Text: (321) 430-8681
