Windsor at Westside Rental Income: What Owners Actually Gross in 2026

The Real Numbers

How Much Does a Windsor at Westside Home Actually Make?

Windsor at Westside is one of the few Kissimmee vacation rental communities where every home was built to be rented. Pulte put up 600+ townhomes and single-family homes here between 2015 and 2020, all 7.5 miles from Animal Kingdom. It also has something most competitor communities do not: an on-site bar and restaurant called Tu Casa.

Our Windsor at Westside owners typically gross between $38,000 and $85,000+ in annual rental income. A 4-bedroom townhome pulling $175 to $250 per night sits at the lower end. A 9-bedroom Clearwater model running $400 to $550 per night sits at the top.

The 34747 zip code median annual revenue is $45,155 with a $237 average daily rate. That includes self-managed listings with bad photos and stale pricing. Professionally managed homes with dynamic pricing consistently clear well above that median.

Property Values

What Windsor at Westside Homes Cost Right Now

Prices at Windsor at Westside range from around $400,000 for a 4-bedroom townhome to $750,000+ for a 9-bedroom single-family home. The community has seven floor plans across three property types. 

Every home comes standard with barrel tile roofing, brick paver driveways, a private heated pool, and stainless steel appliances.

Model	Beds/Baths	Sq Ft	2026 Price Range
Watermarke (TH)	4BD/3.5BA	2,102	$400K-$470K
Castaway (TH)	5BD/4.5BA	2,263-2,264	$415K-$520K
Hideaway (SFH)	6BD/4.5BA	3,275	$540K-$600K
Seashore (SFH)	7BD/5.5BA	3,434	$700K-$720K
Baymont (SFH)	7-8BD/6BA	4,032	$610K-$740K
Clearwater (SFH)	9BD/6BA	4,369	$658K-$665K

The Baymont is the most popular floor plan. At 4,032 square feet with 8 bedrooms, it hits the sweet spot between purchase price and rental income. The Clearwater gives you the highest bedroom count at 9, but the Baymont often produces better returns per dollar invested.

Median sold price per square foot sits at $174 as of mid-2026, down from the previous year. Buyers right now are getting more home for their money than at any point since 2021, which is one reason Windsor at Westside keeps landing on lists of top Orlando rental communities.

Revenue

Estimated Gross Rental Income by Bedroom Count

Property Type	Nightly Rate	Annual Gross
4BD Townhome	$175-$250	$38,000-$48,000
4-5BD Single-Family	$200-$300	$45,000-$58,000
5-6BD Single-Family	$250-$375	$55,000-$70,000
7-8BD Single-Family	$325-$475	$65,000-$80,000
8-9BD Single-Family	$400-$550	$75,000-$85,000+

These are gross revenue figures from our managed portfolio. The range within each tier comes down to furnishing quality, whether the owner invested in a game room or themed bedrooms, and how aggressively pricing is managed.

March is the strongest month in the 34747 zip code with $407 ADR and 76% occupancy. September and October are the slowest. The gap between a professionally managed property and a self-managed one is widest during shoulder seasons, when smart pricing keeps occupancy high while self-managed owners sit empty. Listings that stay ranked high on Airbnb year-round capture more of that off-peak demand.

Expenses

What It Costs to Own a Windsor at Westside Rental

Windsor at Westside carries higher fixed costs than Polk County communities like Solterra or Windsor Island, mainly because of Osceola County’s 13.5% total tax rate (versus 12% in Polk) and the separate HOA and CDD fees. That said, the community’s closer Disney proximity and on-site dining amenities help produce higher average nightly rates that typically offset the higher cost structure.

Monthly and Annual Fixed Costs (8BD Baymont example, $700K purchase)

Expense	Monthly	Annual
HOA (50′ lot)	$410	$4,920
CDD Assessment	~$243	~$2,910
Property Tax (~1.26%)	~$735	~$8,820
Homeowners Insurance	~$400-$500	~$4,800-$6,000
Pool Heating/Maintenance	~$200-$300	~$2,400-$3,600
Utilities (electric, water, gas)	~$400-$600	~$4,800-$7,200
Total Fixed (before PM fee)	~$2,388-$2,788	~$28,650-$33,450

The HOA at Windsor at Westside covers more than most communities. Your $410/month (for 50-foot lots) includes guard gate staffing, trash valet, cable TV, internet, full lawn care, irrigation, and all resort amenities. Our property maintenance team handles everything else.

The CDD assessment is a separate line item that confuses first-time buyers. It covers infrastructure debt and runs about $2,910/year for a 50-foot lot home, collected through your property tax bill.

Net Income

What You Actually Keep After All Costs

Here is a straightforward net income scenario for a 7-8 bedroom Baymont purchased at $700,000 and grossing $72,000 in annual rental income.

Item	Amount
Gross Rental Income	$72,000
Less: Property Management (20%)	-$14,400
Less: HOA + CDD	-$7,830
Less: Property Tax	-$8,820
Less: Insurance	-$5,400
Less: Utilities	-$6,000
Less: Pool Maintenance	-$3,000
Less: Repairs/Supplies (~5%)	-$3,600
Estimated Net Income	$22,950

That is roughly a 3.3% cash-on-cash return before mortgage considerations and tax deductions. With a 25% down payment ($175,000) at current rates, many owners break even or run slightly positive on cash flow while building equity through appreciation and depreciation deductions.

What Makes the Difference

Why Some Windsor at Westside Homes Earn 30-40% More

We manage properties across multiple communities in the Kissimmee corridor, and the performance gap between the top 20% and the bottom 20% at Windsor at Westside is around 30-40% in gross revenue. Same floor plan, same neighborhood, different results. 

Here is what separates them.

The on-site bar and restaurant matters

Tu Casa Bar and Lounge gives Windsor at Westside an advantage most communities cannot match. When a family compares two similar 7-bedroom homes on Airbnb, the one where they can walk to dinner without loading everyone into the car wins. Our listings that highlight Tu Casa in the photo carousel see measurably higher click-through rates.

Themed rooms and professional photos drive rates

A home with a custom Star Wars room, a princess bedroom, and a game room books at $50-$75/night higher than the same floor plan with generic furniture. The Baymont and Clearwater models have enough space upstairs that converting the loft into a game room is standard for top performers.

Dynamic pricing versus set-it-and-forget-it

The 34747 zip code has 7,176 active listings. Owners who set one price and leave it for months lose money during peak season and sit empty during shoulder season. Our pricing adjusts daily based on demand signals, competitor pricing, local events, and booking velocity. We layer manual reviews on top because software alone misses things like Spring Break start dates varying by school district.

Guest screening and communication protect your income

One bad guest can cost $5,000-$10,000 in damage and lost bookings. We screen every reservation through Truvi with $50,000 in damage protection per incident. Strong guest communication before and during every stay prevents most issues before they start.

Turnover quality and multi-platform distribution

Professional turnover cleaning between guests is non-negotiable for five-star reviews. We list on Airbnb, VRBO, Booking.com, Expedia, Google Vacation Rentals, and our own direct booking site. Having a local manager in Kissimmee who handles all of this is what separates top-performing homes from the rest.

Owner Intel

Windsor at Westside Rules and Requirements Every Owner Needs

Windsor at Westside is purpose-built for vacation rentals. The HOA allows short-term rentals and nearly every home in the community operates as one. That said, there are rules, and Osceola County has its own licensing requirements that trip up first-time owners.

Licenses you need before your first guest arrives

Florida requires a DBPR vacation rental license for every property used for stays under 30 days. Osceola County requires a separate Business Tax Receipt. You also need to register for Tourist Development Tax collection with the Osceola County Tax Collector and for Florida sales tax with the Department of Revenue. Miss any of these, and you risk fines, back taxes, and a cease-and-desist from the county.

Tax collection is your responsibility

This is the part that catches Osceola County owners off guard. Unlike some Florida counties, Osceola County does NOT work with Airbnb or VRBO for automatic tax remittance. You are responsible for collecting the full 13.5% from every booking and filing with both the state and county on schedule. We handle all of this for managed properties.

HOA rules that actually get enforced

Parking violations are the most common fine at Windsor at Westside. Guest vehicles must park in designated areas only. Fines are $500 per violation with a $3,000 aggregate cap. Noise ordinances are enforced. No pets at the clubhouse or pool areas (service animals excepted). The 24-hour guard gate means the community takes these rules seriously.

How It Compares

Windsor at Westside vs. Other Kissimmee and Davenport Resorts

Feature	Windsor at Westside	Windsor Island	Solterra	ChampionsGate
County	Osceola	Polk	Polk	Polk
Total Tax Rate	13.5%	12%	12%	12%
To Animal Kingdom	7.5 mi	~12 mi	~15 mi	~10 mi
On-Site Dining	Yes (Tu Casa)	No	No	Varies
Bedroom Range	4-9BD	4-9BD	4-7BD	3-14BD
Price Range	$400K-$750K+	$400K-$800K+	$350K-$650K+	$300K-$1.5M+
Builder	Pulte	Pulte/Mattamy	Mattamy	Various
Guard Gate	24-hour staffed	Yes	Yes	Yes

Windsor at Westside trades a 1.5% higher tax rate for closer Disney proximity and the only on-site restaurant in this comparison group. On $70,000 gross revenue, the extra tax costs about $1,050/year. But the closer distance and Tu Casa can push nightly rates $15-$30 higher than comparable homes further from the parks. Over 200+ booked nights, that more than covers the difference.

The question is not which community has the lowest costs. It is which one puts the most money in your pocket after everything is paid. We manage properties across all four of these communities, plus Davenport rentals further south, and can walk you through the numbers for any specific home.