Windsor at Westside Property Management in Kissimmee, FL
Windsor at Westside is one of Kissimmee’s top-performing Disney-area vacation rental communities. FunStay Florida provides full-service vacation rental management for Windsor at Westside owners at a 15-25% management fee, with no startup costs and no long-term contracts. Our owners typically earn $45,000 to $85,000+ in annual gross rental revenue, depending on property size
Windsor at Westside is a gated resort community built by Pulte Homes in 2015, located at 2100 Tripoli Court in Kissimmee, FL 34747. The resort sits approximately 10 minutes from Walt Disney World via toll road 429, making it one of the closest vacation rental communities to the Disney parks in the Orlando area.
The community features 4 to 9-bedroom single-family pool homes and townhomes, all within a resort-style setting that guests love. For property owners, Windsor at Westside offers a strong combination of location, amenities, and year-round demand from families visiting Disney, Universal Studios, and the surrounding Kissimmee attractions.FunStay
Florida currently manages multiple vacation rental properties at Windsor at Westside. We handle everything from Airbnb and VRBO listing optimization to dynamic pricing, professional cleaning and turnover, and 24/7 guest communication. Our management fee is 15-25% of booking revenue with zero startup costs.
What Makes Windsor at Westside a Top-Performing Rental Community
The resort amenities at Windsor at Westside are a major reason guests choose to book here over hotel stays. Every property in the community gives guests full access to these resort features.
10,000 Sq Ft Clubhouse
The community clubhouse is the centerpiece of Windsor at Westside. At 10,000 square feet, it includes a fully equipped fitness center, game room, and event space. Guests consistently mention the clubhouse in reviews.residents.
Lazy River and Waterslide Pool
The resort-style pool complex features a lazy river, waterslide, splash pad, and heated pool areas. For families with kids, this is often the deciding factor when choosing between competing rentals near Disney.
Tu Casa Bar and Lounge
The on-site Tu Casa Bar and Lounge gives guests a place to relax without leaving the resort. This is a unique amenity that most competing communities in the Kissimmee area don’t offer.
Sports and Recreation
Sand volleyball courts, a fitness center, and walking trails round out the recreation options. These amenities help properties at Windsor at Westside earn higher nightly rates and longer stays than comparable homes without resort access.
How Much Can You Earn at Windsor at Westside?
Windsor at Westside rental income varies by property size, amenities, and how well the listing is optimized. Here are the estimated annual gross revenue ranges for properties managed by FunStay Florida in the Kissimmee area.
| Property Type | Bedrooms | Avg Nightly Rate | Est. Annual Revenue |
|---|---|---|---|
| Townhome | 4 BR / 3 BA | $175 – $250 | $38,000 – $48,000 |
| Single Family Pool Home | 4 – 5 BR | $200 – $300 | $45,000 – $58,000 |
| Single Family Pool Home | 5 – 6 BR | $250 – $375 | $55,000 – $70,000 |
| Single Family Pool Home | 7 – 8 BR | $325 – $475 | $65,000 – $80,000 |
| Large Pool Home | 8 – 9 BR | $400 – $550 | $75,000 – $85,000+ |
Revenue estimates based on FunStay Florida’s portfolio performance data for Kissimmee-area properties. Actual results depend on property condition, furnishing quality, guest reviews, and seasonal demand. Properties with game rooms, themed bedrooms, and private pool/spa combinations typically perform at the higher end of these ranges.
Want to know exactly what your Windsor at Westside property could earn? We provide free, personalized rental income projections based on your specific property, bedroom count, and current condition.
Image from Windsor at Westside Resort’s website.
What We Handle for Windsor at Westside Owners
FunStay Florida provides full-service vacation rental management for Windsor at Westside properties. Every service below is included in our 15-25% management fee.
Dynamic Pricing Strategy
We adjust rates daily based on local demand, Disney park schedules, school holiday calendars, and competitor pricing at Windsor at Westside. Manual weekly reviews combined with automated pricing algorithms keep your revenue maximized year-round.
Listing Setup and Optimization
Professional photography, keyword-optimized listing descriptions, and Rankbreeze SEO tools help your Windsor at Westside property rank higher on Airbnb, VRBO, and Booking.com search results. We also list on Expedia and Google Vacation Rentals.
24/7 Guest Communication
Every guest inquiry, booking question, and mid-stay request is handled by our team around the clock. Fast response times protect your Superhost status and keep guest reviews high. We average a 4.81-star rating across all managed properties.
Professional Cleaning and Turnover
Our cleaning teams know Windsor at Westside properties inside and out. Every turnover follows a detailed checklist, with photo verification before every guest check-in. Pool service, lawn care, and pest control are coordinated separately to keep your property guest-ready.
Maintenance and Emergency Repairs
When something breaks at your Windsor at Westside property, we handle it. Our network of licensed local contractors covers plumbing, HVAC, appliance repair, and pool maintenance across the Kissimmee area. Owners approve all expenses over a pre-set threshold.
Licensing, Permits, and Tax Compliance
Florida requires specific short-term rental permits and tax registrations for vacation rental properties in Osceola County. We handle the paperwork, renewals, and tax remittance so you stay compliant without the headaches.
Multi-platform distribution included: Every Windsor at Westside property is listed on Airbnb, VRBO, Booking.com, Expedia, and Google Vacation Rentals, plus our direct booking site at FunStayHomes.com (zero commission on direct bookings).
You See Everything. No Surprises.
FunStay Florida owners get full visibility into their property’s performance through our owner portal. No guesswork, no waiting for monthly emails.
Real-Time Calendar
See every booking, blocked date, and inquiry across all platforms in one view.
Revenue Reports
Monthly breakdowns showing gross revenue, fees, expenses, and your net payout.
Expense Tracking
Every maintenance call, cleaning charge, and supply purchase is logged and visible.
Guest Screening
Truvi screening on every booking with $50,000 damage protection per incident.
How We Compare to Other Windsor at Westside Property Managers
Not all property management companies serving Windsor at Westside are the same. Here is how FunStay Florida stacks up on the things that actually affect your bottom line.
| Feature | FunStay Florida | Industry Average |
|---|---|---|
| Management Fee | 15-25% | 20 – 30% |
| Startup Costs | $0 | $500 – $2,000 |
| Long-Term Contract | None required | 6 – 12 months typical |
| Booking Platforms | 5 + direct booking site | 1 – 3 platforms |
| Dynamic Pricing | Daily + manual review | Set and forget |
| Guest Screening | Truvi ($50K protection) | Basic ID check or none |
| Owner Portal | Real-time dashboard | Monthly PDF reports |
| Direct Booking Channel | FunStayHomes.com (0% commission) | Not available |
| Local Team | Kissimmee-based, on the ground | Remote / call center |
When Guests Book at Windsor at Westside
Windsor at Westside benefits from year-round Orlando tourism demand. Understanding seasonal patterns helps us price your property for maximum revenue.
Jun – Aug
Peak Season
School summer break. Highest demand from families visiting Disney World and Universal Studios. Longest average stays.
Dec – Jan
Holiday Peak
Christmas, New Year, and winter break travel. Premium nightly rates. Many guests book 6+ months ahead.
Mar – May
Spring / Easter
Spring break waves from across the US. Consistent midweek bookings. Great occupancy for larger homes.
Sep – Nov
Value Season
Lower rates attract deal-seekers. Still profitable with smart pricing. Halloween and Thanksgiving create demand spikes.
Guest Profiles That Drive Revenue at Windsor at Westside
Knowing who books helps us market your property to the right people. Here are the guest profiles we see most often at Windsor at Westside in the Kissimmee area.
Multi-Family Disney Groups
~45% of bookings
Two or three families traveling together to Disney World. They need 5-8 bedrooms, a private pool, and a game room to keep kids entertained between park days. These guests book the largest homes and spend the most per stay.
Avg stay: 5-7 nights
Book ahead: 3-6 months
Peak: Summer, holidays
Single-Family Vacationers
~30% of bookings
A family of 4-6 looking for a Disney-area home with a pool. They book 4-5 bedroom townhomes or smaller single-family homes. Price-sensitive but willing to pay more for properties with great reviews and resort amenities.
Avg stay: 4-5 nights
Book ahead: 1-3 months
Peak: Spring break, summer
Celebration and Event Groups
~15% of bookings
Birthday trips, bachelor/bachelorette parties, reunions, and milestone celebrations. These groups want the biggest houses with the best pools and game rooms. They book premium properties and often add extra services.
Avg stay: 3-4 nights
Book ahead: 2-4 months
Peak: Year-round
Extended Stay and Snowbirds
~10% of bookings
Remote workers, traveling nurses, and northern snowbirds who stay 2-8 weeks. Lower nightly rate but consistent revenue. These guests are low-maintenance and treat the property well. Value season gold.
Avg stay: 14-30+ nights
Book ahead: 1-2 months
Peak: Sep-Feb
How Windsor at Westside Owners Get Started with FunStay Florida
From your first call to your first booking, here is what the process looks like. Most Windsor at Westside owners see their property listed and earning within 7 to 10 days.
What Property Owners Say About FunStay Florida
⭐⭐⭐⭐⭐
“We switched from the resort program after three years of flat revenue. Mike’s team had our 6BR villa on five platforms within two weeks. Revenue jumped 38% in the first full quarter. The dashboard alone was worth the switch. I can see exactly what my home earns every single day.”
6BR Villa, Heritage Crossing, Reunion Resort
⭐⭐⭐⭐⭐
“I own three properties at Reunion and one in Champions Gate. FunStay manages all four. What I appreciate most is the property-specific strategy. My 12BR estate gets completely different pricing and marketing than my 3BR condo. That granular approach makes a real difference in total portfolio returns.”
Multiple Reunion Resort Properties
⭐⭐⭐⭐⭐
“The dual-county permit situation had me confused for months. FunStay handled everything, figured out my property was actually in Orange County (not Osceola like I assumed), and got my permits sorted correctly. That kind of local knowledge is hard to find with bigger management companies.”
4BR Townhome, Reunion Resort, Kissimmee
Mike Chen, Founder
Licensed FL Realtor (La Rosa Realty) | Airbnb Superhost | 10+ Years in Vacation Rentals
Mike started FunStay Florida with a single vacation rental purchase and grew it to over 100 managed properties across Central Florida. He is based in Kissimmee, FL and personally oversees property management operations at Windsor at Westside and other resort communities in the Orlando area. Whether you are a first-time investor or adding to your portfolio, Mike and his team can help you maximize your Windsor at Westside property’s earning potential.
Windsor at Westside Property Management FAQ
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Whether you just bought your first vacation home or you are looking for better management for an existing rental, we are here to help. No pressure, no long-term commitment. Just a conversation about what your property could earn with FunStay Florida.
Call or text: (321) 430-8681
Email: Mike@FunStayHomes.com
Based in Kissimmee, FL (local to Windsor at Westside)
