Windsor Hills Resort Property Management
Stress-Free Hosting Starts Here—I Handle It All for You.
Let your Windsor Hills vacation home earn more while I handle guest messages, dynamic pricing, turnovers, cleanings, reviews, and compliance.
As an Airbnb Superhost, Property Manager, local Realtor, and fellow investor, I help homeowners like you unlock serious passive income through Airbnb property management in Windsor Hills Resort.
🎯 Get a Free Income Estimate Today
Superhost Rated 4.8+ | Full-Service Airbnb Property Manager | Local Realtor | 10+ Years of Results
Mike Chen – Vacation Home Expert
Best Property Manager in Windsor Hills Resort
⭐⭐⭐⭐⭐ 4.81-star rating on Airbnb with 10+ Years Hosting Experience
What You Get with Our Full-Service Windsor Hills Property Management
You didn’t buy a vacation home to be a full-time host. That’s where I step in.
As a Superhost, licensed Realtor, and Windsor Hills local, I handle the day-to-day work that keeps your property profitable and your guests happy. Whether you’re just starting out or fed up with a management company falling short, I’ll take care of it all like it’s my own.
Here’s what full-service short-term rental management actually means for both property owners and guests:
| What We Handle | How We Do It |
| Listing Setup & Visibility | Listings on Airbnb, VRBO, Google, and more—complete with keyword-rich copy and strategy to stand out and convert. |
| Photos That Pop | Professional, scroll-stopping photography that highlights your home’s best features and drives more clicks. |
| Smart Pricing = Stronger Profits | Daily rate adjustments based on local trends, seasonality, and competitor data to help you earn more. |
| 24/7 Guest Communication | We respond to every guest question—day or night. No bots. Just real, local support that keeps your reviews glowing. |
| Cleanings That Guests Notice | Hotel-quality cleanings between every stay, with detailed checklists and linen restocks so everything’s spotless. |
| Maintenance, Covered | From AC issues to pool problems, we coordinate fast, reliable repairs with vetted local vendors before guests even notice. |
| Compliance Made Easy | We handle permits, taxes, and HOA rules so you stay compliant without lifting a finger. |
| Owner Dashboard & Income Reports | Full visibility with live calendar access, earnings reports, and booking insights—all in one easy-to-use portal. |
Why Windsor Hills Owners Choose FunStay Florida
Not all Windsor Hills Airbnb property management is created equal.
Big-box companies might promise easy hosting but deliver long wait times, hidden fees, rotating reps, and vague results. We do things differently.
At FunStay Florida, we offer hands-on, Orlando short-term rental management that’s built to protect your time and maximize your income. Whether you’re just getting started or frustrated with a hands-off company, we’re here to ensure your property performs.
Here’s What We Offer That Others Don’t:
| 🏷 Feature | ✅ FunStay Florida | ❌ Big-Box Managers |
| Local Windsor Hills Team | Yes | No – Often Remote |
| Realtor® + Superhost Owned | Hands-on Experience | Lacks Hosting Background |
| Transparent Flat Pricing | No Hidden Fees | Add-On Charges |
| Dynamic Pricing Strategy | Custom to Your Home | Basic Algorithms |
| Airbnb, VRBO, Booking.com Exposure | Multi-Channel Listings | Airbnb Only |
| Dedicated Account Manager | You Work With Me Directly | Rotating Staff |
| SEO-Optimized Listings | Written for Search + Guests | Basic Copy/Paste Templates |
When I Manage Your Windsor Hills Vacation Rental—It’s Personal
✔ Respond to guests at midnight so you don’t have to
✔ Monitor pricing daily to capture peak demand
✔ Coordinate cleanings, repairs, and last-minute bookings
✔ File taxes, follow HOA rules, and protect your property’s reputation
✔ Handle guest reviews, claims, and long-term guest relationships
My goal is to make owning an Airbnb in Windsor Hills profitable, easy, and hands-off, without the guesswork.
📞 Let’s talk about what’s not working—and how we can fix it.
Why Windsor Hills Resort Is Built for Airbnb Success
If you’re looking for a property that guests love and that performs consistently well as a short-term rental, Windsor Hills Resort is one of the best in the Disney area.
Prime Location That Keeps Guests Booking
Just 2 miles from Walt Disney World, Windsor Hills offers that rare mix of convenience and comfort. Theme parks? 10 minutes away. Dining and shopping? Right down the road. Yet guests still get the peace of a gated, resort-style community.
It’s a location that shows up on nearly every vacationer’s search and delivers on expectations.
Vacation Homes Built to Perform
Whether it’s a 2-bedroom condo or a 6-bedroom pool home, Windsor Hills properties are made for hosting, floor plans are vacation-friendly, layouts support families and groups, and many homes include game rooms, private pools, and themed bedrooms that drive both bookings and higher nightly rates.
This kind of versatility makes Windsor Hills ideal for owners looking to maximize ROI.
Resort-Style Amenities Guests Actually Use
Windsor Hills isn’t just “close to Disney”—it’s a destination in itself. The amenities here aren’t window dressing; they’re vacation drivers.
Guests enjoy:
- A massive 140,000-gallon lagoon-style pool
- Water park with dueling slides & splash pad
- Game room, movie theatre, and fitness center
- Tennis courts, putting green, & playgrounds
- The Marketplace & Grill for food and drinks
- 24/7 guard-gated entry for added peace of mind
For guests, that means fun-filled days without leaving the community. For you, it means better reviews and repeat bookings.
Zoned for Short-Term Rentals
Windsor Hills Resort is 100% short-term rental approved, with no gray areas, no restrictions, and no worrying whether your investment is allowed to operate. The HOA is experienced in vacation rentals and structured to support them.
High Demand = Smart Investment
Windsor Hills remains one of the most popular vacation rental communities in Central Florida, year after year. Homes here consistently rank well on Airbnb and VRBO, and owners benefit from strong occupancy, high average daily rates, and reliable cash flow.
We can do much more than your Airbnb property management.
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.
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.
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 Hills Resort
“Windsor Hills is one of the most trusted vacation rental communities in Kissimmee—just minutes from Disney and built for high occupancy. With its waterpark, clubhouse, and 24/7 gated security, it’s a favorite among families and group travelers. We manage properties here and in nearby resorts like Windsor Palms, Windsor Island, and Solara too.”
We’re Owners Too—So We Get It
Hi, we’re FunStay Florida. We manage Airbnb homes in Windsor Hills 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 Hills and other top Kissimmee communities.
We built FunStay Florida to take the pressure off owners like you. You’re not alone if you’re tired of juggling guests, cleanings, or underperforming listings. That’s where our Airbnb property management in Windsor Hills Resort comes in, hands-on, strategy-driven, and completely local.
From listing setup to guest communication, maintenance, and revenue optimization, we handle every part of the process so you can earn more with less hassle.
If you want Superhost-level service and Airbnb host support that’s built for results, we should 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 Hills 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 Hills Resort?
We offer flat-rate pricing, no setup fees, no long-term contracts, and no hidden charges. As a Superhost-run property management company in Windsor Hills, we focus on boosting your vacation rental ROI, not stacking on surprise fees. Want a custom quote? Call or text Mike directly.
Can I still stay in my home when I want?
Of course! You’re always in control. Just block off the dates you want to use your Windsor Hills home, and we’ll work the calendar around your personal schedule simple and flexible.
How do you help me earn more from my property?
We increase bookings through SEO-optimized listings, multi-channel exposure (Airbnb, VRBO, Google Vacation Rentals, and more), and real-time dynamic pricing. Our local Windsor Hills property management team monitors guest demand, events, and trends so your listing stays competitive and booked.
What makes you different from other Windsor Hills property managers?
We’re not a call center, we’re a hands-on, local team led by a licensed Realtor and Airbnb Superhost. We live nearby, manage our own properties, and know exactly what it takes to stand out in Orlando’s short-term rental market. That’s why so many owners trust us as the best property manager in Windsor Hills Resort.
Do you handle guest issues, cleanings, and maintenance?
Yes 100%. We manage all guest communication, coordinate professional cleanings and linen restocks, and handle maintenance issues through our trusted local vendors. Whether it’s a 10 p.m. lockout or a broken pool heater, we’ve got it covered so you don’t have to.
Is Windsor Hills good for short-term rental?
Absolutely. Windsor Hills Resort is one of the most popular short-term rental communities near Disney World. With 24/7 gated security, resort-style amenities, and a prime Kissimmee location, this neighborhood consistently delivers high occupancy rates and strong rental income.
I’m new to Airbnb hosting—can you help me start from scratch?
Definitely. We offer full-service Airbnb host services in Windsor Hills, including furnishing guidance, permits, listing setup, and pricing strategies. Whether you’re a first-time host or a seasoned investor, we’ll get your home guest-ready and earning fast.
Can you help me get started if I’m brand new to hosting?
Yes we’ve helped many first-time owners launch successful listings from the ground up. From furnishing tips and vendor referrals to permitting, listing setup, and pricing strategy, our Airbnb host services in Windsor Hills are designed to simplify every step. We’ll make sure your property looks great, performs well, and checks every compliance box.
How fast can you get my Windsor Hills Resort home listed on Airbnb?
Fast. Once your home is guest-ready and we have the photos, we typically launch within 7–10 days. We handle everything from writing a high-converting listing to syncing calendars, setting up dynamic pricing, and getting you on boarded across Airbnb, VRBO, Google Vacation Rentals, and more.
What if I already have a listing but it’s not performing well?
We specialize in turning around underperforming listings. Whether it’s outdated photos, missing keywords, or a weak pricing strategy, we’ll audit your current setup and make improvements that help you get more bookings, better reviews, and stronger returns. Our vacation rental management in Windsor Hills is built for results not guesswork.
How do I know I can trust you with my property?
We understand it’s more than just a house, it’s your investment. That’s why we stay personally involved in every home we manage. FunStay Florida is led by a local Airbnb Superhost and Windsor Hills property manager who also owns short-term rentals. We don’t hand you off to a call center. We treat your home like we treat our own with care, accountability, and proven systems.
