Property Management in Windsor Cay
Windsor Cay Resort wasn’t built for average vacation homes, so why settle for average Airbnb management?
Windsor Cay is one of the newest and most in-demand short-term rental communities near Orlando. Just minutes from Disney, it features resort-style pools, lazy rivers, water slides, and vacationers who expect a 5-star stay from booking to checkout.
I’m Mike Chen — licensed Florida Realtor, Airbnb Superhost, Property Manager, and full-time vacation rental owner.
I started FunStay Florida to give Windsor Cay homeowners like you the kind of expert, full-service Airbnb property management I always wanted for my own investments—hands-on, data-driven, and 100% local.
✅ Superhost-run & locally operated in the Disney area
✅ No setup fees. No long-term contracts. No fine print.
✅ Listed across Airbnb, VRBO, Booking.com, Expedia & Google
Mike Chen | Email: Mike@FunStayHomes.com
Owner of FunStay Homes and Realtor at La Rosa Realty, Specializing in Vacation Home Sales and Acquistions.
⭐⭐⭐⭐⭐ 4.81-star rating on Airbnb with 10+ Years Hosting Experience
Full-Service Property Management for Windsor Cay Resort
Booked Solid. Cleaned Right. Managed Locally.
Managing a vacation rental in Windsor Cay Resort shouldn’t feel like guesswork. From listing to turnover, we handle it professionally, locally, and with Superhost standards.
Listing Setup & Optimization
Get your Windsor Cay property seen and booked.
We build and launch your listing across all major platforms with a conversion-focused strategy.
✔ Airbnb, VRBO & Google Vacation Rentals
✔ SEO-optimized listing copy that ranks and converts
✔ Pro-level photography that makes your home scroll-stopping
✔ Smart pricing setup based on the Windsor Cay market demand
Daily Operations & Maintenance
We handle the day-to-day so you don’t have to.
No more texting cleaners or wondering if the AC got fixed—we’ve got it covered.
✔ 24/7 guest messaging and booking support from our local Windsor-area team
✔ Trusted cleaning crews and vendor coordination
✔ Turnover checklists, inspections, and stock tracking
✔ Live owner dashboard with booking data and monthly earnings
5-Star Guest Experience
Happy guests = better reviews, more bookings, and fewer headaches.
We deliver a stay worth 5 stars every time.
✔ Personalized guest check-in guides and local recommendations
✔ In-stay communication and quick support
✔ Review monitoring and feedback follow-up
✔ Damage claim management & guest satisfaction tracking
How It Works
Getting Started Is Simple—Here’s How We Do It
STEP 1
Schedule a Call with Mike
Strategy call to understand your property, goals, and identify improvement areas
STEP 2
Create a Custom Plan
You’ll get a tailored Airbnb management strategy designed around your home.
STEP 3
List Your Home, Unlock Earnings
While you get paid, we’ll take care of listings, guest support, cleaning, pricing, and more.
No stress. No guesswork. Just a smarter way to manage your Airbnb.
Why Windsor Cay Resort Is Built to Win on Airbnb
You didn’t just buy a vacation home, you bought into one of the most guest-loved, host-ready communities in the Disney area.
From a booking perspective, Windsor Cay checks every single box. When travelers search Airbnb for the ultimate Orlando escape, this resort consistently lands on their shortlist, and here’s why:
Resort-Style Amenities Guests Actually Search For
This isn’t your average vacation neighborhood—it’s a mini waterpark, family hub, and staycation dream all in one.
✅ Zero-entry resort pool with water slides & lazy river
✅ Private rental cabanas for poolside lounging
✅ Children’s splash pad + shaded playground
✅ Community clubhouse with event space and café
✅ Full bar + grab-and-go snack options
✅ Arcade & game room for family fun
✅ Fitness center with cardio and weights
✅ Basketball & volleyball courts for active travelers
✅ Walking trails and open green space
✅ 24-hour manned gated entry for peace of mind
✅ Full-service concierge & onsite activities director
✅ Community room for events or private gatherings
When guests see “Windsor Cay” on a listing, they already know the experience will be next-level.
Prime Location = Premium Bookings
Located just off US-27 near US-192, Windsor Cay offers that sweet spot between peaceful retreat and theme park proximity.
- 🚗 15 minutes to Walt Disney World
- 🛒 10 minutes to Margaritaville, Sunset Walk, and shopping
- 🎢 25–30 minutes to Universal and SeaWorld
- 🍽️ Surrounded by restaurants, groceries, and attractions
This kind of location gives you broad guest appeal—families, snowbirds, convention travelers, and staycationers all book here.
Why It Performs So Well on Airbnb
Guests love the balance of luxury and fun. Owners love the booking consistency and high nightly rates.
- Homes with private pools = higher demand
- 5–8 bedroom layouts = group travel goldmine
- Resort fees are reasonable, and guest expectations are high
Most homes are new or recently built = lower maintenance costs
Your Windsor Cay Property Deserves More Than “List It and Hope for the Best”
We don’t just manage, we maximize. As your local Superhost-run property management team here in Windsor Cay Resort, we handle every detail that others miss, and it shows in your reviews, revenue, and repeat bookings.
We make your listing irresistible.
Professional photography, keyword-rich descriptions, and multi-platform visibility (Airbnb, VRBO, Google) to get your Windsor Cay home seen and booked fast.
We price smart—every day.
Using dynamic pricing tools, seasonal data, and local event tracking, we adjust your nightly rates in real time to stay ahead of the competition and keep your income strong.
We handle every guest message.
From late-night check-in texts to follow-up reviews, our local Windsor Cay team provides 24/7 Airbnb Superhost service—no bots, no waiting, just real support.
We keep it guest-ready. Always.
Our cleaning teams follow strict checklists, restock essentials, and inspect between every stay. You’ll never have to wonder if the home is ready—it always is.
We handle the surprises.
AC not cooling? Pool heater acting up? We coordinate fast with vetted local vendors so issues are resolved quickly—without you lifting a finger.
We manage the red tape.
Permits, taxes, HOA rules—we’ve got them covered. Windsor Cay’s short-term rental guidelines aren’t new to us. You stay compliant while we handle the paperwork.
You get clear reporting on your terms.
Track bookings, income, and calendar updates through your owner dashboard. No spreadsheets. No confusion. Just full visibility and control.
Ditch the Big Box. Go Local with FunStay Windsor Cay Management
“I don’t just manage vacation rentals—I live this business every day. I’m a Superhost, a licensed Florida Realtor®, and an investor who knows exactly what it’s like to trust someone else with your home. That’s why I built FunStay Florida: to offer Superhost-run property management that actually delivers, right here in Windsor Cay Resort. Local, hands-on, and built for serious results.”
—Mike Chen, Local Expert, Airbnb Superhost & Windsor Cay Property Manager
When it comes to Airbnb property management in Windsor Cay Resort, most big-name companies offer the same generic, hands-off approach. At FunStay Florida, we do things differently—because your home deserves more.
| What You Get | FunStay Florida | Big-Box Companies |
| Local Windsor Cay-Based Team | ✅ Yes | ❌ Remote call center |
| Realtor® + Superhost Owned | ✅ Yes | ❌ No STR experience |
| Transparent Flat Pricing | ✅ Yes | ❌ Hidden fees |
| Smart Pricing Strategy | ✅ Manual + tech-powered | ⚠️ Basic automation |
| Listings on Airbnb, VRBO, Google & More | ✅ Yes | ❌ Airbnb-only |
| You Work Directly With Mike | ✅ Yes | ❌ Rotating reps |
| SEO-Optimized Listings | ✅ Custom written | ❌ Copied templates |
| Onboarding & Setup Help | ✅ Hands-on | ❌ DIY only |
No pressure. Just honest answers from someone who knows Windsor Cay Resort.
Our Airbnb Property Management Services for Windsor Cay Resort
Your property will be listed on Airbnb, VRBO, Booking.com, Expedia, Google Vacation Rentals, and more. The more platforms you’re on, the more bookings you’ll see—and we handle it all for you.
Areas (Resorts) We Serve
Orlando
- Solterra Resort
- ChampionsGate Resort
- Storey Lake Resort
- Reunion Resort
- The Bear’s Den- Reunion
Davenport
- Magic Village
- Solara Resort
- Windsor Cay Resort
- Paradise Palms
Not sure if we manage your area?
Let’s find out together.
Your Superhost & Local Property Manager for Windsor Cay Resort
“I know Windsor Cay Resort is one of the most exciting new short-term rental communities in Central Florida. With its resort-style water park, vacation-friendly homes, and unbeatable location near Disney, it’s built for Airbnb success. We’ve helped homeowners here attract 5-star guests, earn more, and stay hands-free, and if you own in nearby resorts like Windsor Island, Solara, or ChampionsGate, we manage those too.”
We’re Owners Too—So We Get It
Hi, we’re FunStay Florida. We manage Airbnb homes in Windsor Cay Resort like they’re our own.
We’re not just another property manager—we’re local Superhosts, licensed Realtors®, and vacation rental owners who know what it takes to deliver 5-star guest experiences in Windsor Cay and nearby Disney-area resorts.
We started FunStay Florida to help owners earn more with less stress. Your home deserves to stand out on Airbnb and major platforms—and we make sure it does.
From listings and pricing to cleanings, permits, and guest messaging, we handle it all.
If you want real results without the guesswork, let’s talk.
Our Owners and Guests Say It Best
⭐⭐⭐⭐⭐
5 STAR REVIEWS
Our guests and owners love what we do—because we treat every stay and every home like it’s our own. From 5-star reviews to higher earnings, the results speak for themselves.
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.
Yezi – Owner
KISSIMMEE, FL
⭐⭐⭐⭐⭐
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.
Daniel – Guest
DAVENPORT, FL
⭐⭐⭐⭐⭐
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.
James Riley- Guest
KISSIMMEE,FL
⭐⭐⭐⭐⭐
We took a chance on a recommendation to switch to FunStay 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.
Donna – Owner
KISSIMMEE, FL
⭐⭐⭐⭐⭐
The place was amazing and fit just right for our family! The amenities that came along with it was excellent. My kids and I had so much fun. Perfect spot and really close to the Disney parks. Michael and his staff were very responsive if we needed something and very friendly. Will definitely book again!!
Jennifer – Guest
KISSIMMEE, FL
⭐⭐⭐⭐⭐
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.
Sarah Thompson,- Guest
DAVENPORT, FL
⭐⭐⭐⭐⭐
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!
Maria – Guest
DAVENPORT, FL
⭐⭐⭐⭐⭐
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!!!
Joe – Guest
ORLANDO, FL
⭐⭐⭐⭐⭐
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!
Benjamin – Guest
KISSIMMEE, FL
⭐⭐⭐⭐⭐
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!!!
Dayna – Guest
Smoky Mountains, TN
⭐⭐⭐⭐⭐
👋 Need Help Managing Your Airbnb in Windsor Cay Resort?
Let’s turn your property into a top-performing vacation rental.
Call or text Mike at (321) 430-8681
Your local Airbnb Superhost & full-service property manager.
Complimentary Vacation Rental Projection & Income Estimate
Enter your Orlando, Davenport or Kissimmee vacation rental address and our team will provide you with an in-depth analysis of your property, along with estimated annual income and occupancy projection.
Real Estate Agent and Owner of FunStay Homes
Call/Text: 321-430-8681
Email: Mike@FunStayHomes.com
Frequently Asked Questions
How much do you charge for Airbnb management in Windsor Cay Resort?
We keep it simple—flat-rate pricing with no setup fees and no long-term contracts. As a Superhost-run property management team, our goal is to boost your vacation rental ROI, not surprise you with fees. Contact Mike for a custom quote based on your Windsor Cay home.
Can I still use my property when I want to?
Yes. You’re always in control. Just block off the dates you want, and we’ll manage the rest around your schedule easily and flexibly.
How do you increase bookings and income for Windsor Cay owners?
We combine SEO-optimized listings, multi-platform exposure (Airbnb, VRBO, Google), and dynamic pricing backed by local demand data. Our team monitors trends daily to keep your rates competitive and your calendar full.
What makes you different from other Windsor Cay property managers?
We’re not just managers but local Superhosts and licensed Realtors who also own vacation rentals. That means we know the market, the guests, and the Windsor Cay community inside and out. There are no call centers, just real, hands-on management.
Do you handle guest messaging, cleaning, and maintenance?
Absolutely. We manage everything: 24/7 guest support, professional cleanings, linen restocking, on-call maintenance, and vendor coordination. You won’t have to lift a finger.
Is Windsor Cay Resort a good place for short-term rentals?
Windsor Cay is one of the newest and most exciting vacation communities near Disney. Its resort-style amenities and prime location make it a top performer for Airbnb bookings year-round.
Can you help me if I’m just getting started?
Yes! From permits to photography to furnishing and listing setup, we walk you through every step. Our full-service Airbnb hosting service is built for both seasoned owners and first-timers.
How fast can you get my Windsor Cay Resort home listed on Airbnb?
Once your home is guest-ready and we have the photos, we can go live on Airbnb, VRBO, and more within 7–10 days. That includes listing creation, calendar sync, dynamic pricing setup, and full onboarding. We move fast, so you start earning sooner.
What if I already have a listing, but it’s not performing well?
We’ve got you. We specialize in optimizing underperforming short-term rentals. Whether it’s better photos, rewritten SEO-focused copy, smarter pricing, or improved guest communication, we’ll get your Windsor Cay listing back on track.
How do I know I can trust you with my property?
We understand—this isn’t just a property, it’s an investment. That’s why we don’t hand you off to a call center. FunStay Florida is run by a Superhost and licensed Realtor who owns and manages Airbnb homes right here in Windsor Cay Resort. We treat your home like we treat our own with care, strategy, and full accountability.
