Property Management in Windsor Island Resort
Stress-free hosting starts here—I manage everything for you.
Maximize your rental income, protect your investment, and give guests five-star experiences with trusted Airbnb property management in Windsor Island Resort.
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Superhost Rated 4.8+ | Full-Service Airbnb Property Manager | Local Realtor | 10+ Years of Results
Mike Chen – Vacation Home Expert
Top Realtor in Orlando Area
Why Windsor Island Resort Is Built for Airbnb Success
Tucked just southwest of Orlando, Davenport, Florida, is quietly becoming one of the hottest destinations for short-term rental investors. Windsor Island Resort isn’t just another vacation community—it’s Davenport’s crown jewel for short-term rental investors.
Tucked just minutes from Disney and Orlando’s biggest attractions, this new-build, gated resort offers the best of both worlds: a resort-style experience for guests and a high-performing investment opportunity for owners. With 4–10 bedroom private pool homes and townhomes, Windsor Island attracts large families, multi-generational travelers, and group getaways all year round.
It’s not just popular—it’s designed to succeed as an Airbnb rental.
Here’s why short-term rental demand stays high at Windsor Island:
- Gated entry with 24/7 security
- Zero-entry resort pool with lazy river, dual water slides, splash pad, and hot tub
- Mini golf, sports courts, fitness center, and clubhouse
- Poolside bar, game room, and onsite entertainment
- Just 8–12 minutes from Walt Disney World Resort
- Surrounded by restaurants, golf, shopping, and major roadways (I-4, US-27)
If you own property here or plan to invest, Airbnb property management in Windsor Island Resort isn’t just an option—it’s your key to long-term, hands-off income.
And we’re here to help you maximize it.
What You Get with Our Windsor Island Resort Property Management Services
At FunStay Homes, we go beyond “Airbnb management.” We deliver white-glove service and a smart strategy tailored specifically for vacation rentals in Windsor Island Resort.
Whether you’re a first-time Airbnb host or a seasoned investor, we’ll handle everything, so you can earn more without lifting a finger.
Our Full-Service Windsor Island Resort Property Management Includes:
- Listing setup + optimization on Airbnb, VRBO, Booking.com & more
- Scroll-stopping professional photography and copywriting that converts
- Dynamic pricing using real-time market data and competitor insights
- 24/7 guest messaging and reservation management
- Hotel-quality cleanings with full linen restocks after each stay
- Maintenance coordination, inspections, and fast damage reports
- Permits, BTR, licensing, and Polk County tax filings—fully handled
- Owner portal with live performance data and monthly payout reports
- Optional concierge & key exchange, stocked welcome kits, and VIP support
We’re local. We’re hands-on. And we treat your Windsor Island property like it’s our own.
Why Owners Choose FunStay Homes Over Big-Box Managers
Not all property management in Windsor Island Resort is created equal.
At FunStay Homes, we’re not some corporate call center halfway across the country. We’re your neighbors. Your local experts. And yes—we’re hosts too.
I’m not just a licensed Realtor—I’m a Superhost with over 10 years of hands-on experience, managing 100+ of properties and earning more than 2,600 five-star reviews.
I live and breathe vacation rental property management in Windsor Island Resort and across Central Florida.
Here’s what makes us different:
| Feature | FunStay Homes | Big-Box Managers |
| Local Windsor Island Team | ✅ | ❌ |
| Airbnb guest support 24/7 | ✅ | ⚠️ Often Outsourced |
| Transparent Flat Pricing | ✅ | ❌ Hidden Fees |
| Realtor & Superhost Owned | ✅ | ❌ No Local Insight |
| Custom Listing Optimization | ✅ | ❌ Generic Templates |
| Dynamic Revenue Strategy | ✅ | ⚠️ Basic Algorithms |
| Guest Communication + eBook | ✅ | ❌ Not Included |
| Multi-Channel Listing Mgmt | ✅ | ⚠️ Airbnb Only |
| Dedicated Local Manager | ✅ | ❌ Rotating Reps |
| SEO-Optimized Listings | ✅ | ❌ Basic Titles Only |
We manage your Windsor Island property like it’s our own:
- Responding to guests at midnight so you don’t have to
- Adjusting pricing daily to capture demand spikes
- Coordinating last-minute repairs, turnovers, and cleanings with local pros
- Managing guest reviews, check-ins, damage claims, and HOA compliance
With FunStay Homes, you’re not hiring a manager—you’re gaining a partner who cares about your Windsor Island Resort vacation rental as much as you do.
More Reach. More Bookings. Smarter Airbnb Property Management
Your home deserves to be seen everywhere guests are searching—not just on Airbnb.
✔ Booking.com
✔ VRBO
✔ Facebook
✔ Instagram
✔ Expedia
✔ Airbnb
We can do much more than your Airbnb property management.
To get the most out of your vacation home, FunStay Florida will advertise your home not just on Airbnb but also on other major booking websites like:
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
The Little (But Powerful) Things I Handle for You
From the second a guest clicks “Book Now” to the moment they leave a glowing review, I make sure your Windsor Island vacation rental is five-star ready—and every detail is handled.
✔️ Cleaning & Maintenance – Your home stays spotless, stocked, and guest-ready with reliable turnover service and regular upkeep.
✔️ Damage & Checkout Inspections – I document, report, and assist with claims so you’re never left in the dark—or out of pocket.
✔️ Compliance Management – I handle permits, licenses, and tax filings for Polk County, so you stay legal without lifting a finger.
✔️ 5-Star Guest Experience – From late-night questions to early check-ins, my team responds quickly and professionally—24/7.
✔️ Ongoing Review Building – We don’t just aim for 5 stars—we build a brand guests remember and rave about.You focus on the income—I’ll sweat the details. That’s the FunStay difference.
Need Help Managing Your Airbnb in Windsor Island Resort?
Let’s Make Hosting Effortless and Profitable
Email: Mike@FunStayHomes.com
Text or Call: (321) 430-8681
Managing a short-term rental in Windsor Island shouldn’t feel like a second job.
Our Owners and Guests Say It Best
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
Got questions? I’ve managed hundreds of vacation rentals—including my own—and I’m here to help you feel confident, informed, and ready to earn more.
Do I need a special permit to run an Airbnb in Windsor Island Resort?
Yes—and don’t worry, I’ll take care of it. As part of our Windsor Island Resort property management services, I handle your BTR registration, Polk County TDT filings, and all local compliance so you stay legal and stress-free.
Can I block off dates to use my home personally?
Absolutely. It’s your home, not a hotel. You can block any dates through your owner portal, and I’ll manage bookings around your schedule.
How soon can we go live?
Most listings go live within 7–10 days after onboarding. I move fast—professional photos, compliance, listing creation, and pricing strategy all happen in-house.
How do I get paid and see results?
You’ll have access to a secure owner dashboard with real-time income reports and monthly payouts. I keep everything transparent so you’re always in the loop.
Do you only manage luxury homes or large properties?
Nope. I manage all types of short-term rentals in Windsor Island Resort, from townhomes to 10-bedroom pool villas. Whether you have one home or a portfolio, I’ll tailor a plan that fits your goals.
Why should I choose FunStay Homes over big-name property managers?
Because I treat your home like it’s mine. I’m not a rotating rep or outsourced assistant. I’m Mike—a Superhost, Realtor, and vacation rental owner just like you. I’ve walked this road, and now I help others do it smarter, with less stress and better results.
What do your Airbnb management services include?
I offer a full-service property management solution—from start to scale. That includes:
- Airbnb listing optimization
- Scroll-stopping professional photos
- Dynamic pricing for vacation rentals
- Marketing across Airbnb, VRBO, Booking.com, and more
- 24/7 guest communication
- Maintenance coordination
- Compliance with Polk County permits and tax filings
Everything’s handled. You just enjoy the income.
How does dynamic pricing for vacation rentals help maximize income?
I use real-time pricing tools that adjust your nightly rate based on local demand, events, seasonality, and competitor trends. That way, your property is always competitively priced and never leaves money on the table—whether it’s a quiet Tuesday or a sold-out holiday weekend.
Will you take care of the photos, listing, and marketing setup?
Absolutely. I handle the entire launch—from professional photography and high-converting listing descriptions to keyword-optimized marketing copy. Your Windsor Island home will be strategically positioned to stand out, attract bookings, and perform better across all platforms.
