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
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—anWindsor 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.
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.
Don’t Just Take Our Word for It—Hear It from Homeowners Like You
Thrilled with My New Property Manager
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.
Thrilled with My New Property Manager
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.
Thrilled with My New Property Manager
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.
More Reach. More Bookings. Smarter Airbnb Property Management
Your home deserves to be seen everywhere guests are searching—not just on Airbnb.
We can do much more than your Airbnb property management.
To get the most out of your vacation home, Casiola will advertise your home not just on Airbnb but also on other major booking websites like:
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?
Managing a short-term rental in Windsor Island shouldn’t feel like a second job.
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.
