$27K-$90K+
Est. Annual Gross
55%
Davenport Avg Occupancy
$255
Davenport Avg ADR
95/100
Market Score
FunStay Florida Portfolio Performance
77%
Avg Occupancy
$286
Avg ADR
4.81★
Guest Rating
100+
Properties Managed
How Much Does a Windsor Island Vacation Home Actually Make?
A new Windsor Island owner called us two months ago. He bought a 6-bedroom Pulte home for $620,000, self-managed it on Airbnb for nine months, and netted about $18,000. He thought something was wrong with the property. Nothing was wrong with the property. Everything was wrong with the pricing, the listing photos, and the guest turnover strategy.
That’s the reality of Windsor Island Resort rental income. The community itself is solid. Pulte built 617 homes between 2020 and 2023, all purpose-built for short-term rental. Every unit sits inside a gated, 24/7 security resort with a lazy river, dual water slides, and a full clubhouse. It’s 8 to 12 minutes from Disney World. Guests like it here.
But the gap between what a well-managed Windsor Island home earns and what a self-managed one earns is not small. I’ve seen 5-bedroom townhomes pull $27,000 on one end and $48,000 on the other. Same floor plan. Same community. Completely different outcomes. We put together a full comparison of property managers at Windsor Island if you want to see where those gaps come from. But first, let’s walk through the actual numbers.
What Windsor Island Homes Cost Right Now
Pulte built six floor plans at Windsor Island, ranging from the 5-bedroom Castaway Interior townhome up to the 10-bedroom Clearwater Grand. All homes include private screened-in pools.
| Floor Plan | Bedrooms | Type | Approx Sq Ft |
|---|---|---|---|
| Castaway Interior | 5 BD | Townhome | 2,271 |
| Winstone | 5 BD | Single-Family | ~2,400 |
| Lakeshore | 5-6 BD | Single-Family | ~2,800 |
| Hideaway | 6 BD | Single-Family | ~2,800 |
| Seashore | Up to 7 BD | Single-Family | ~3,200 |
| Clearwater Grand | 10 BD / 8 BA | Single-Family | 4,398 |
Current asking prices run $458,690 to $995,000. The average selling price is $654,873, which is about 3.6% below asking. There are 122 homes listed for sale right now, with 56 sold in the past year. That’s a buyer’s market. If you’re looking to get into Windsor Island, you have negotiating room. Understanding the full cost to run a short-term rental starts with knowing what you’re paying for the property itself.
Estimated Gross Rental Income by Bedroom Count
There’s no publicly available income data specific to Windsor Island. So I built these projections from Davenport-wide market data (AirDNA, AirROI), Windsor Island nightly rates from OTA platforms, and our own portfolio performance numbers. These are estimates, not guarantees.
The Davenport vacation rental market scores 95 out of 100 on AirDNA. Average annual revenue across all property types is $27,500 with 55% occupancy and $255 ADR. Our Windsor Island managed properties outperform those numbers significantly.
| Bedrooms | Est. Gross Revenue (Annual) | Est. ADR Range |
|---|---|---|
| 5 BD (Townhome) | $27,000 – $48,000 | $150 – $220 |
| 5-6 BD (Single-Family) | $36,500 – $61,300 | $200 – $280 |
| 7-8 BD | $46,000 – $76,300 | $280 – $380 |
| 9-10 BD | $51,100 – $90,300 | $350 – $450 |
Those ranges are wide for a reason. Peak season (March, June through August, December) drives 40-45% of your annual revenue. The bottom of each range reflects self-managed properties with static pricing. The top reflects professionally managed homes using dynamic pricing across multiple booking platforms.
Why the range matters:
The Davenport market averages $27,500 in annual revenue at 55% occupancy. FunStay Florida properties average 77% occupancy and $286 ADR. That difference is not the property. It’s the management.
What It Costs to Run a Windsor Island Rental
Windsor Island has one major advantage over resorts like ChampionsGate or Solterra: the HOA is all-inclusive. Your monthly payment covers 24/7 gate security, lawn maintenance, valet garbage, internet, cable TV, and full resort amenity access. No separate club bills. No surprises.
Here is a realistic annual expense breakdown for a 6-bedroom single-family home (roughly $620,000 purchase price).
| Expense | Annual Cost |
|---|---|
| HOA Fees (all-inclusive) | $4,680 – $7,200 |
| Property Tax (incl. CDD ~$2,000) | $10,800 – $13,900 |
| Insurance (STR-specific) | $2,500 – $4,000 |
| Utilities (electric + water) | $3,600 – $5,400 |
| Pool Heat (seasonal, 6-8 months) | $600 – $1,800 |
| Maintenance & Repairs | $2,000 – $4,000 |
| Furnishing Replenishment | $1,000 – $2,000 |
| Licensing & Permits | $200 – $300 |
| Total (excl. PM & mortgage) | $25,380 – $38,600 |
The all-inclusive HOA advantage:
At ChampionsGate, you pay a master HOA, a sub-HOA, and a separate club fee. At Solterra, it’s HOA plus club. At Windsor Island, one bill covers everything from security to internet to landscaping. Monthly HOA runs $390 to $410 according to the official HOA, though some all-in cost guides report $550 to $600 when you factor in total carrying costs.
Furnishing cost:
Budget $40,000 to $70,000 to furnish a Windsor Island home before you earn a single dollar. This is not optional. Poorly furnished homes sit empty while the mortgage runs. The ROI on quality furnishing pays for itself within the first year.
Want us to run these numbers for your specific property?
We give Windsor Island owners a free rental projection based on their floor plan, bedroom count, and furnishing level.
What You Actually Keep
On a 6-bedroom Windsor Island home grossing $50,000 per year with $32,000 in total expenses (including property management at 15%), your net is roughly $18,000 before mortgage. A well-managed 7-bedroom pulling $65,000 gross with $38,000 in expenses nets about $27,000.
Those numbers do not include your mortgage. Most investors putting 25-30% down on a $620,000 home are close to breakeven or slightly positive in year one. Income climbs as reviews stack and occupancy stabilizes through year two and three. If you want to run the math on your own property, our vacation home ROI calculator walks through the full formula with a real Orlando case study.
You also need to factor in 12% tax on every booking: 6% Florida sales tax, 5% Polk County tourist development tax (TDT), and 1% county discretionary surtax. Airbnb collects all three automatically in Polk County. VRBO does not collect the 5% Polk County TDT, so if you’re on VRBO, you’re responsible for remitting that yourself. Direct bookings mean you collect and remit everything.
Read the full Florida vacation rental tax breakdown before you list.
Polk County vs. Osceola County tax advantage:
Windsor Island sits in Polk County, where the total tax rate is 12%. Resorts in Kissimmee (Osceola County) pay 13.5%. On $50,000 in gross bookings, that’s $750 per year you keep by being in Polk County instead of Osceola.
Why Some Windsor Island Homes Earn 30-40% More
The revenue ranges above are wide because four things separate top earners from the rest.
Dynamic pricing. Static nightly rates leave money on the table during spring break and price you out during September. We use dynamic pricing that adjusts rates daily based on demand, local events, and competitor pricing. Our portfolio averages $286 ADR compared to the Davenport market average of $255.
Guest experience. Windsor Island’s resort amenities get guests in the door. The lazy river, dual water slides, splash pad, and clubhouse give families a reason to book here over a random Davenport rental. What keeps them coming back is what happens inside your home. We screen every guest through Truvi, which includes $50,000 in damage protection per incident. Clean homes with responsive guest communication earn repeat bookings and better search placement.
Multi-platform distribution. Most self-managing owners list on Airbnb only. We distribute across Airbnb, VRBO, Booking.com, Expedia, and Google Vacation Rentals. More channels means more visibility and fewer empty nights. We break down exactly how this works in our multi-platform booking strategy guide.
Professional management. Self-managing from out of state sounds like it saves money. It usually costs money. Missed maintenance, slow guest responses, and flat pricing add up. The owners in our portfolio who switched from self-management saw a 15-25% revenue increase within 12 months. No renovations. Just better operations, better pricing, and 24/7 guest support through our Davenport property management team.
Windsor Island Rules Every Owner Needs to Know
Windsor Island is a purpose-built short-term rental community. There are no long-term residents. Every home was designed to be rented. That’s good for investors because there’s no HOA fighting against vacation rentals.
But the HOA (managed by Castle Group) has strict rules you need to follow.
120-day guest limit. No individual guest can stay more than 120 days per calendar year. Some third-party sites incorrectly list this as 30 days. The official HOA FAQ confirms 120 days.
Guest registration through Proptia. Every guest must be registered in the Proptia system before arrival. If they’re not in the system, they will be denied entry at the gate. You or your property manager needs to add all guests before check-in.
Parking limits vary by home type. 50’s-style homes get 5 vehicles (2 garage, 2 driveway, 1 street). 40’s-style homes get 4 vehicles. Townhomes get 3 vehicles in designated areas. No RVs allowed in the community at any time, not even for loading.
No mail delivery. USPS does not deliver to Windsor Island. UPS, FedEx, and Amazon can deliver to the property address, but the clubhouse will not accept packages.
Business Tax Receipt required. Every Windsor Island unit must have a BTR, even if it’s not actively being rented. The community is classified as short-term rental, so the BTR requirement applies across the board. We handle all licensing and permits for our managed properties.
We handle every item on this list for our managed properties. If you want the full regulatory breakdown for Davenport, read our Florida vacation rental tax guide.
Windsor Island vs. Other Davenport Resorts
Windsor Island is one of the newer resort communities in Davenport. Here is how it stacks up against the competition.
| Feature | Windsor Island | Solterra | ChampionsGate |
|---|---|---|---|
| Builder | Pulte Homes | Lennar | Multiple |
| Built | 2020-2023 | 2015-2018 | 2000s-2020s |
| Total Units | 617 | ~400 | 1,500+ |
| BD Range | 5-10 | 4-14 | 3-14 |
| HOA Structure | All-inclusive | HOA + Club separate | Master + Sub + Club |
| Price Range | $458K-$995K | $400K-$1.2M | $350K-$2M+ |
| Annual CDD | ~$2,000 | $2,500-$4,000 | ~$3,000 |
| Key Amenity | Lazy river + slides | Large amenity center | Oasis + golf |
Windsor Island’s newer construction (2020-2023) means lower near-term maintenance costs and updated building codes, which can reduce insurance costs. The all-inclusive HOA structure is simpler to budget than the multi-bill setups at ChampionsGate and Solterra. And the CDD assessment at ~$2,000 per year is lower than both competitors. For the full income breakdown on Solterra, read our Solterra rental income guide.
Want to Know What Your Windsor Island Home Could Earn?
We manage Windsor Island properties with a 15-20% flat-rate fee. No hidden charges. No long-term contracts. Real income projections based on your specific floor plan and bedroom count.
Mike Chen is the founder of FunStay Florida and a licensed realtor specializing in vacation rental properties across Davenport, Kissimmee, and Greater Orlando. He manages 100+ short-term rentals with a 4.81-star average guest rating across Windsor Island, Solterra, ChampionsGate, Reunion, and other Central Florida resort communities.
Want to explore Windsor Island management? Visit our Windsor Island property management page or call (321) 430-8681.
