Every Size Works. They Are Not the Same Business.
Townhomes & Five-Bedroom Homes
The lowest entry price in the community. The trade-off is competition — many similar listings — so design and pricing decide the result. Furnishing costs are the lowest of any tier.
Six & Seven-Bedroom Homes
Real group capacity without a villa-level budget — dual owner's suites on separate floors, two distinct living areas, and fewer competing listings above six bedrooms. For most first-time vacation rental buyers this is the balance point.
Eight to Ten-Bedroom Villas
The highest cash flow potential and the smallest pool of competing listings — multi-family groups book these homes. It is also the largest total budget once furnishing is included, and the tier where design makes the biggest difference.
Today, getting from this stretch of US-27 to Disney's western gateway means running south to US-192 and back up Avalon Road — a detour every guest feels on arrival day. Sawgrass Bay Boulevard and Flemings Road are being connected across the Lake–Orange county line to remove it. Lake County finished its side; the Orange County half broke ground in late 2025 under a 14-month schedule, targeting spring 2027.
Local reporting timed the current workaround at roughly 23 minutes with no traffic. The new connection is expected to cover the same ground in under five, and it gives this corridor a direct line to SR-429 and Western Way — the road into Disney's western parks, itself being widened from four lanes to six.
"Minutes to Disney" is one of the most searched attributes in this market. Once the connector opens, Windsor Cay will be among the shortest drives to Disney on the US-27 corridor.
The purchase price is not the full cost. A large villa costs much more to furnish and equip than a townhome. Compare homes on the total budget — purchase plus furnishing.
The final phase is releasing now, and lot position matters — proximity to the clubhouse, pool orientation, and how much usable outdoor depth the lot gives you.
Tell us your budget and we will tell you which tier it fits.
Every home in Windsor Cay has a screened lanai and a private heated pool. In almost every listing in the community, that space is treated as leftover square footage — a table, four chairs, and whatever the builder installed.
We treat it as the most valuable room in the house. In Florida, it is where a family spends its evenings, and it is the photo that decides whether a listing gets clicked.
We put more of the design budget into the outdoor space than most designers do. It is the biggest reason our homes here out-earn similar houses on the same street.
Both are strong options. Windsor Cay has the newer homes, the available builder inventory and the new road coming.
If you haven't purchased your vacation home yet, we can introduce you to our recommended Vacation Rental Expert Realtor — Orlando's top Resort and Second-Home Certified partner who knows the market and the business.
The exact checklist we run on an underperforming rental — pricing, listing, operations and design — so you can see where your income is leaking.
Windsor Cay runs from five-bedroom townhomes to ten-bedroom villas across roughly 2,270 to 4,380 square feet. All of them can perform. What changes is the required budget and the earning potential.
Same builder, overlapping floorplans, near-identical amenity sets. The managed portfolio includes both, and we would still steer a new buyer toward one of them.
The newest Windsor — and the one that fixed the small frictions owners notice at the others.
Unedited guest reviews from homes we designed and set up, now in the managed portfolio.
Is Windsor Cay a good short-term rental investment?
It is currently the community where the homes in the managed portfolio perform best. It is zoned and purpose-built for short-term rental, the amenity set is complete and open, the final phase is still releasing from the builder, and the 2027 road connection shortens the drive to Disney.
How long is the drive to Disney from Windsor Cay?
Roughly eight to nine miles, typically 15 to 25 minutes depending on traffic and which park. The Sawgrass Bay–Flemings connection, targeted for spring 2027, is expected to remove the US-192 and Avalon Road detour and give this corridor a direct route to SR-429 and Disney’s western gateway.
Which floorplan should I buy?
It depends on your available budget. The eight to ten-bedroom villas produce the highest cash flow and face the least competition. Six and seven-bedroom homes are the balance point for most first purchases. Townhomes and five-bedroom homes return well against their entry price but compete with many similar listings, so design and pricing decide the result. Compare tiers on the total budget — purchase plus furnishing — rather than purchase price alone.
Windsor Cay or Windsor Island?
The managed portfolio includes both. Windsor Island is sold out and resale-only, with more traffic at the entrance during peak check-in times. Windsor Cay is newer, still has builder inventory, and stands to gain from the road connection. With no other constraints, we would buy in Windsor Cay today.
Why do you focus so much on the outdoor space?
Because in Florida it is where guests spend their evenings, and because it is the most under-designed space in almost every listing in the community. It is the easiest place to create a real difference. We walk owners through our specific approach directly.
Do you manage townhomes and smaller homes here?
Yes. The model centers on single-family homes with private pools from five bedrooms up, and the managed portfolio includes townhomes in Windsor Cay that perform well against their purchase price. They demand more from the design and more discipline on pricing, because there are more competing listings — which is where management that partnered with the designer from day one has an advantage.
Can you show me real performance data before I commit?
Yes. We benchmark through KeyData and can show you where comparable homes in Windsor Cay actually sit — including where your own home sits, if you already own here.