863-443-6890 Let's Talk
Aerial view of a Davenport resort community

Polk County

Windsor Island, where the presale dues estimates did not survive contact.

Dues are running about 40% above what buyers were quoted before delivery, there is a 120-day cap on individual stays, and towing is enforced. All knowable in advance.

The numbers, with where each one came from
HOA dues≈$550–$600 / monthUnconfirmed — verify with the associationUp roughly 40% from presale estimates. Any figure sourced from builder-era marketing is now wrong.Listing and association data, via VHG Resort Cost Index · verified Aug 2026
CDD assessment$1,227–$2,374 / yearFY2025 adopted district budget, via VHG Resort Cost Index · FY2025 budget
Minimum lease termNo community-wide minimumUnconfirmed — verify with the associationMinimums are set per listing. On the maximum side the association caps how long any one individual may stay at 120 days.Association FAQ, via VHG community research · verified Aug 2026
Short-term rental positionPermitted — purpose-built for itGuest-stay cap and strict towing enforcement are the operational constraints, not the rental permission itself.Polk County zoning + association documents · verified Aug 2026
Combined lodging tax12% combined6% state + 1% surtax + 5% tourist development tax.Polk County Tax Collector + Florida DOR · verified Aug 2026
Nightly rate (market proxy)$255–$291 / night (market)Unconfirmed — verify with the associationLarge Windsor Island homes commonly list $350–$700+. Market-level proxy.AirDNA / AirROI Davenport market, TTM · mid-2026
Occupancy (market proxy)40–55%Unconfirmed — verify with the associationPeak February–April; trough July and September.AirROI 40.5% / AirDNA 55%, Davenport market TTM · mid-2026

Windsor Island is one of the newer purpose-built resort communities on the Polk side, and its defining financial fact is that the dues buyers were quoted before delivery are not the dues they pay now — the current schedule runs roughly 40% above presale estimates. If you are working from a number you saw during the sales process, or from a listing repeating one, it is stale.

Two operational rules matter more here than in most communities. The association caps how long any single individual may stay in the community at 120 days, which is a constraint worth understanding if you had any thought of long-stay or snowbird use alongside nightly rental. And towing is enforced strictly — a small thing until a guest review mentions it.

Figures are current as of the dates shown and change. The HOA figure could not be confirmed from a primary source — verify with the association. Rate and occupancy are market-level proxies, not measured community performance.

Homes for sale

What’s available in Windsor Island Resort right now

Live MLS inventory for this community is being wired in. Until it is, I will just send it to you — the current listings, what each one really carries per month once dues and the district assessment are in, and the ones I would skip.

Send me what’s available → See my current listings

Run it yourself

Windsor Island Resort’s numbers, in the calculator

The short-term rental calculator opens preloaded with this community’s nightly rate, occupancy, dues and district assessment, so you are arguing with real figures rather than a generic default. Every field is still editable.

Open the calculator with these numbers →

Windsor Island Resort suits you if

  • You want newer construction with a strong amenity package on the Polk side, at 12% lodging tax rather than Osceola’s 13.5%.
  • You are buying large. The product here runs to substantial homes and that is the segment this market pays for.
  • You want a purpose-built rental community where the position is not in doubt.

Look elsewhere if

  • You are working from a presale dues figure. Current dues run roughly 40% above what buyers were originally quoted.
  • You had any plan involving long personal stays — the association caps any one individual at 120 days in the community.
  • You want the lowest district assessment available. It is moderate here, not absent.

Due diligence

Before you write an offer here

  1. The current dues schedule, not the builder-era one. Anything sourced from presale marketing is now materially wrong.
  2. The 120-day guest-stay cap and how the association enforces it, if long stays are any part of your plan.

I do all of this before you are emotionally attached to a house, and I put the answers in writing. It is the part of the job that actually saves people money.

Video

A walk through Windsor Island Resort

I am filming community tours — the amenities, the drive to the parks, and the parts the marketing photos leave out. Not up for this one yet. Ask me and I will walk it on video with you live instead, which is better anyway because you can point the camera.

Book a live video walk →

Compare

How Windsor Island Resort stacks up

Solterra Resort

Lowest dues in the corridor and the highest district assessment. The clearest proof that HOA is the wrong number to shop on.

See the numbers →

Windsor Cay

Lake County's 11% lodging tax, Airbnb collects the tourist tax, and no county business tax — the least paperwork anywhere here.

See the numbers →

Windsor at Westside

Capable resort, but the published dues figures conflict badly and the district's operating charge jumped sharply.

See the numbers →
All 15 communities, side by side

Common questions

Windsor Island Resort questions

Why are Windsor Island's dues higher than I was quoted?
Because the presale estimates did not survive the real operating budget — current dues run roughly 40% above what buyers were originally told. If your figure came from the sales process or from a listing repeating it, it is stale. Get the current schedule from the association.
What is the 120-day rule?
The association caps how long any single individual may stay in the community at 120 days. It rarely affects ordinary nightly rental, but it does constrain long-stay or snowbird use alongside it, so build it into the plan rather than discovering it.
Is Windsor Island in Polk or Osceola?
Polk County, on the Davenport side. That means a 12% combined lodging tax rather than Osceola's 13.5% — a small but real edge on every booking across a full year.

The other half

Want the full tour of Windsor Island Resort?

This page is about whether the numbers work. For everything inside the gates — the amenity stack, the floor plans by builder, what the resort is actually like to stay in — I keep a much longer community guide on my other site.

Read the Windsor Island Resort deep dive →

Let's Talk

Looking at Windsor Island?

Send me the address and I will get the current dues schedule rather than the presale one, the district’s assessment for that lot, and the association’s actual rules on guest stays — before you underwrite anything.

Call or Text
863-443-6890
Email
john@vacationhomehelp.com
Book a Call
Grab a time on my calendar →
Serving
Orange, Osceola & Polk Counties, Florida

Get a straight answer

I read every one of these myself. Usually back to you same day.

By sending this you're asking me to reach out — nothing more. No obligation, no representation agreement, and I don't sell or share your information.