Is Windsor at Westside a Good Investment? A 2026 Data-Driven Analysis

Short answer: Yes, Windsor at Westside can be a good investment, but only if you buy at the right price and manage it well. Our team at FunStay Florida manages multiple properties in this community, and I have seen the rental income numbers from both sides of the transaction. This post breaks down exactly what you can expect to earn, what it costs to own, and where the risks are.

Disclosure: I am a licensed realtor who sells homes in Windsor at Westside, and my property management company (FunStay Florida) manages vacation rentals there. Revenue figures cited from FunStay reflect our professionally managed portfolio. I will clearly note when data comes from our operations versus independent third-party sources.

Windsor at Westside at a Glance

Median Sold Price

~$510K

Range: $387K-$749K

HOA / Month

$379-$410

Includes internet, cable, lawn

Distance to Disney

~7.5 mi

10-15 min drive

Total Homes

592

496 SF + 96 townhomes

Windsor at Westside is a guard-gated resort community in Kissimmee, FL, built by Pulte Homes between 2015 and 2020. The community is fully built out, so every purchase is a resale. It sits in Osceola County, zoned as STRPD (Short Term Rental Planned Development), which means nearly 100% of homes operate as vacation rentals. There is no ambiguity about STR legality here.

These are fee-simple single-family homes and townhomes, not condotels. That distinction matters for financing: you can use standard conventional loans (Fannie Mae/Freddie Mac) without the warrantability headaches that come with condotel purchases.

A quick note on search terms: some buyers search for “Windsor at Westside condos for sale.” There are no condos here. The community offers townhomes (4-5 bedrooms, ~2,100-2,263 sq ft) and single-family pool homes (5-10 bedrooms, ~2,490-4,398 sq ft).

Amenities That Drive Bookings

Guest amenities are not just nice-to-have features for vacation rentals. They directly affect your nightly rate and booking volume. Windsor at Westside’s amenity package is competitive for its price point:

• 10,000 sq ft clubhouse (“The Club”), Mediterranean-themed
• Pool complex: Zero-entry resort-style pool, double waterslide, lazy river, hot tub/spa, kids’ splash zone, family cabanas
• Tu Casa Bar and Lounge: On-site covered Tiki bar (one of the few resort communities with this)
• Fitness center, video arcade, and 9-hole mini-golf
• Sports courts: Basketball, sand volleyball, tennis, soccer field
• Lake with pier, playground, green spaces, sundry shop

Every home includes a private heated pool. That is standard in the community, not an upgrade. In our experience, the lazy river and waterslide complex is the amenity that most frequently appears in guest reviews.

How Much Rental Income Can You Earn?

Windsor at Westside Airbnb Income by Bedroom Count

Whether you list on Airbnb, VRBO, or Booking.com, the rental income potential at Windsor at Westside depends heavily on bedroom count and management quality. The following projections come from our FunStay Florida portfolio. These represent professionally managed properties using dynamic pricing. Self-managed properties typically earn less.

How Does That Compare to the Broader Market?

For independent context, here is the Kissimmee market-wide data from AirROI (2026):

• Average daily rate: $290
• Average occupancy: 44.8% (median 49%)
• Average annual revenue: $35,205
• Top 25% of listings earn: $5,686+/month ($68K+/year)
• Top 10% of listings earn: $8,337+/month ($100K+/year)

Source: AirROI, Kissimmee FL, 2026

Our FunStay portfolio rental income projections for Windsor at Westside fall in the top 25% to top 10% range of the Kissimmee vacation rental market. That is not because this community is uniquely better. It is because professional management with dynamic pricing, professional photography, and optimized listings consistently outperforms the market median.

Seasonal Breakdown

Source: AirROI Kissimmee 2026, StaySTRA

March is the strongest month. September is the weakest. Peak periods (spring break, summer, holidays) generate roughly 40-45% of your annual revenue. If you are building a financial model, do not average out the months evenly. The seasonality swing is significant.

What Does It Actually Cost to Own? (Full Carrying Cost Breakdown)

This is where most Windsor at Westside investment analyses fall short. Gross rental income means nothing without a clear picture of carrying costs. Here is the full breakdown:

HOA Fees ($379-$410/month)

This community has some of the lowest HOA fees among comparable resort communities, and the coverage is unusually comprehensive:

• 24-hour staffed guard gate
• Full lawn maintenance, fertilizing, and irrigation
• High-speed internet (Spectrum bulk contract)
• Basic cable TV
• Daily trash valet service
• Access to all resort amenities

For comparison: Windsor Hills charges $505-$567/month, Solterra charges $500-$650/month, and Solara charges $503-$760/month. The community delivers more comprehensive coverage at a lower price point.

The HOA is managed by Castle Group.

CDD Assessment (~$1,144/year)

The community has a Community Development District (CDD). The CDD assessment appears on your property tax bill as a non-ad valorem assessment. Based on available listing data, the annual CDD assessment is approximately $1,144/year, though this figure should be verified with the current CDD budget before purchasing.

Property Taxes

The community is in Osceola County. Vacation rental properties do not qualify for homestead exemption, so you pay the full non-homesteaded rate. Based on the research brief, expect approximately $6,000 to $10,600+ per year depending on assessed value. Always verify the exact amount with the Osceola County Property Appraiser before purchasing.

Insurance

Florida rental property insurance has increased roughly 40% over the past two years. Budget $3,000-$8,000+ per year depending on coverage level and home size.

Property Management

Professional management fees in the Kissimmee vacation rental market typically run 15-25% of gross booking revenue, based on our experience and competitor pricing. Self-management saves this cost but requires hands-on involvement in guest communication, cleaning coordination, maintenance, and pricing.

Utilities and Maintenance

Budget for electric, water, pool maintenance, pest control, and general upkeep. Exact figures will vary by home size, occupancy, and season. Homes built 2015-2020 are now 6-11 years old, so expect increasing maintenance on HVAC, pool equipment, and appliances. Ask your property manager for a detailed expense history on any specific property you are evaluating.

STR Licensing and Taxes

• Florida DBPR License: $155 initial + $155 annual renewal
• Osceola County registration: Required through county Growth Management
• Tax burden: ~12-13.5% combined (6% state sales tax + ~6% Osceola County Tourist Development Tax). Major platforms like Airbnb and VRBO remit these automatically.

ROI Analysis: Sample Investment Scenarios

Important: The scenarios below use FunStay Florida revenue projections (first-party data) and publicly available cost data. Actual results will vary based on purchase price, financing terms, management quality, and market conditions. These are not guarantees.

Scenario A: 4BR Townhome at ~$400K

Note: Property tax and utility estimates are based on typical Osceola County rates for this property type and value range. Verify with current tax records.

At a $400K purchase price, that puts the cap rate in the range of 2.6-3.1% before debt service. Townhomes generate the lowest total revenue but also have the lowest entry price and maintenance costs. For cash buyers, the returns may work; for financed buyers, the margins are tight.

Scenario B: 7BR Single-Family at ~$550K

Note: Property tax and utility estimates are based on typical Osceola County rates for this property type and value range. Verify with current tax records.

At $550K, this implies a cap rate of roughly 4.9-6.0%. The larger homes generate proportionally more revenue while fixed costs like HOA and CDD stay the same, which is why they tend to produce better returns on a percentage basis.

Scenario C: 9BR Estate at ~$700K

Note: Property tax and utility estimates are based on typical Osceola County rates for this property type and value range. Verify with current tax records.

At $700K, the cap rate comes to roughly 4.3-4.6%. Larger estates generate the highest gross revenue, but the higher acquisition cost, property tax, and maintenance compress the return percentage compared to the 7BR sweet spot.

Where Does Your Revenue Go?

The chart below breaks down how each dollar of gross revenue is allocated for the 7BR scenario (Scenario B), which represents the strongest risk-adjusted return in this community.

Gross revenue$72,500

Total expenses$42,564

Net operating income$29,936

You keep41.3%

Net operating income 41.3%Property management 20%Property tax 12.4%Utilities + maintenance 11%Insurance 6.9%HOA 6.8%CDD 1.6%

Midpoint estimates from Scenario B. Based on FunStay Florida revenue projections and publicly available cost data. Not a guarantee.

What Bedroom Count Performs Best?

Based on our management data and market-level RevPAR figures from StaySTRA, larger homes generate higher total revenue but also cost more to buy and maintain. The sweet spot depends on your budget and risk tolerance.

RevPAR: StaySTRA Orlando STR Data 2026. Entry prices: estimated from active MLS listings at time of writing (overall community range: $387K-$749K per neighborhoods.com). Revenue: FunStay Florida.

The 6-7 bedroom single-family homes tend to offer the best balance of revenue versus acquisition cost at Windsor at Westside. The 8-9 bedroom estates generate more gross revenue, but the higher purchase price and increased maintenance costs can compress your return percentage.

One caution from BiggerPockets investor discussions: “Large homes either bring lots of kids or lots of parties, and both are destructive.” Larger properties may require higher maintenance reserves.

Pros and Cons for Investors

Strengths

• Purpose-built STR community with STRPD zoning. No regulatory risk.
• Disney proximity (7.5 miles, 10-15 min drive)
• Lowest HOA among comparable communities ($379-$410/mo) with the most comprehensive coverage
• Fee-simple single-family homes = standard conventional financing, no warrantability issues
• Pulte construction with 10-year structural warranty
• Current buyer leverage: 258 avg days on market and 97% list-to-sale ratio mean room to negotiate
• Epic Universe demand boost (25-36 min drive)
• Diverse configurations (4-10 BR) for different guest segments

Risks

• Significant price depreciation: Phase 1 saw -26% median decline YoY, far worse than Kissimmee’s -3.7%
• High days on market (258 avg): Poor exit liquidity if you need to sell quickly
• Kissimmee STR oversupply: 10,688+ active listings, supply up 53.7% YoY
• Party/noise reputation: TripAdvisor shows 3.0/5, with complaints about late-night events
• Community aging: Homes are 6-11 years old. Expect rising maintenance costs.
• Insurance escalation: Florida rental insurance up ~40% over two years
• No homestead exemption: Full non-homesteaded property taxes
• Solterra price comparison: Per BiggerPockets, Solterra was ~$70K cheaper with similar 30-day revenue

How Windsor at Westside Compares

vs.Windsor HillsEst. 2004

Windsor at Westside wins

• Lower HOA: $379-$410 vs. $505-$567/mo
• Newer construction: 2015-2020 vs. 2004-2010
• Up to 9-10 BR vs. max 6 BR
• Better amenities: lazy river, waterslides, Tiki bar

Windsor Hills wins

• Closer to Disney: ~2-3 mi vs. 7.5 mi
• 20-year track record with loyal repeat guests
• Lower entry prices starting ~$180K

Verdict: Windsor Hills for maximum Disney proximity. Windsor at Westside for newer, larger homes at lower monthly carrying cost.

vs.SolterraTop forum comparison

Windsor at Westside wins

• Much closer to Disney: 7.5 mi vs. 15-20 mi
• Lower HOA: $379-$410 vs. $500-$650/mo
• On-site Tiki bar (neither Solterra nor most competitors offer this)

Solterra wins

• ~$70K cheaper at similar bedroom counts
• Similar 30-day revenue per BiggerPockets investors
• Better ROI on paper due to lower entry price

Verdict: Solterra for pure yield-focused buyers. Windsor at Westside if Disney proximity and lower HOA are priorities.

vs.Storey LakeDirect competitor

Windsor at Westside wins

• Lower HOA fees across the board
• Lazy river + waterslide complex
• Tu Casa Tiki Bar on-site

Storey Lake wins

• Better walkable location: near grocery and restaurants on Osceola Pkwy
• Stronger brand recognition on booking platforms

Verdict: Windsor at Westside for amenities and lower costs. Storey Lake for location convenience and booking visibility.

For a side-by-side look at more communities, see our guide to the top resorts to buy a vacation home near Disney World.

Is 2026 a Good Time to Buy at Windsor at Westside?

The honest answer: it depends on your investment timeline.

The case for buying now: Prices have dropped significantly (-26% YoY in Phase 1). Properties are sitting on market for 258 days on average, and sellers are accepting 97% of asking price. That means you have real negotiating power. You can likely acquire a property well below replacement cost, which is a fundamentally strong position for a long-term hold.

The case for caution: The broader Kissimmee STR market has 10,688+ active listings and supply grew 53.7% year-over-year. Revenue per listing has been under pressure. If you are counting on rapid price appreciation, the data does not support that expectation right now.

The demand drivers are real. Orlando remains one of the most-visited destinations in the world, and Universal’s Epic Universe (opened 2025) added another major attraction within 25-36 minutes of Windsor at Westside. These are structural demand drivers, not temporary trends.

If you buy at today’s depressed prices, manage the property professionally with dynamic pricing, and hold for 5+ years, the fundamentals support a positive outcome. Weigh the pros and cons carefully: the rental income potential is real, but so are the risks. Windsor at Westside is a good investment for the right buyer at the right price. It is not the right play if you are looking for a quick flip or counting on above-market appreciation.

Frequently Asked Questions

Can you use Airbnb at Windsor at Westside?

Yes. Windsor at Westside is zoned STRPD (Short Term Rental Planned Development). Nearly 100% of homes operate as vacation rentals. You need a Florida DBPR license ($155) and Osceola County registration, which takes 2-4 weeks.

Is the community still being built?

No. Windsor at Westside is fully built out. Pulte completed both phases between 2015 and 2020 and has moved on to Windsor Cay. Every purchase is a resale.

What financing is available?

Standard conventional financing (Fannie Mae/Freddie Mac) is available because these are fee-simple single-family homes, not condotels. Investment property loans typically require 15% down, 620+ credit score, and 6 months of reserves. DSCR loans are also available for investors who prefer to qualify on rental income rather than personal income (20-25% down, 660+ credit).

What property management options are available?

Multiple property management companies operate at Windsor at Westside, including FunStay Florida (our company). Fees in this market typically range from 15-25% of gross booking revenue. In our experience, professionally managed properties with dynamic pricing, professional photography, and optimized listings consistently outperform self-managed properties.

Are there any noise or party concerns?

This is a real issue to consider. TripAdvisor reviews (3.0/5, 105 reviews) and investor forums mention late-night parties and noise complaints, particularly on weekends. The HOA has a 24-hour guard gate and rules against events, but enforcement can be inconsistent. Professional management companies typically have guest behavior policies and noise monitoring tools that reduce this risk for individual owners.

How does the HOA compare to other communities?

Windsor at Westside’s HOA ($379-$410/month) is among the lowest for resort communities in the Disney corridor. It also includes more than most: internet, cable, full lawn maintenance, irrigation, and daily trash valet are all covered. Windsor Hills charges $505-$567, Solterra charges $500-$650, and Solara charges $503-$760 for comparable or lesser coverage.

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