Evaluating Windsor Cay As A Short‑Term Rental Investment

If you are looking at Windsor Cay as a short-term rental play, the big question is not whether Orlando draws visitors. It does. The real question is whether a specific home in this community can carry its fixed costs, taxes, and day-to-day operating load while still meeting your return goals. If you want a clearer way to evaluate the opportunity before you write an offer, this guide will walk you through the numbers and the pressure points that matter most. Let’s dive in.

Why Windsor Cay Gets Investor Attention

Windsor Cay Resort is a new Pulte community in Clermont at 1217 Emerald Row Street, with homes specifically marketed for short-term rental use. The lineup includes 5-bedroom townhomes and 5- to 10-bedroom single-family homes, and every home includes a private heated pool. The amenity package is also built around vacation use, with a lazy river, dual waterslides, mini-golf, arcade, tavern and grill, fitness center, sports courts, splash pad, concierge, and a 24-hour manned gate.

That combination matters because guests in the Orlando area often compare homes on more than just price. Private pools, bedroom count, and resort-style amenities can shape booking appeal, especially for larger travel groups. Windsor Cay is clearly positioned to compete for that kind of stay.

Orlando Demand Supports the Story

A short-term rental community works best when it sits near a deep visitor base, and that is one of Windsor Cay’s biggest strengths. Visit Orlando reported 75.3 million visitors in 2024 and 76.7 million in 2025, with Orlando remaining the most visited destination in the United States. In both years, 81% of visits were domestic leisure trips.

That matters for investors because Windsor Cay is not trying to create demand from scratch. It is tapping into an already massive leisure market that also includes a high volume of overnight visitors. Visit Orlando reported 49.2 million overnight domestic travelers in 2025 alone.

Pulte’s materials place Windsor Cay in Clermont with access via US-192 and US-27 and describe it as close to Orlando attractions, shopping, dining, and entertainment. The builder also shows the clubhouse now open, which is important when you are evaluating present-day guest appeal rather than future promises.

Home Types and Price Points

Windsor Cay offers a wide spread of product types, and that gives you several ways to approach the investment. Current examples shown by Pulte include:

• 5-bedroom townhome, 2,269 square feet, priced at $608,190
• 5-bedroom single-family Winstone, 2,490 square feet, starting at $649,990
• 5-bedroom Lakeshore, 2,611+ square feet, starting at $689,990
• 6-bedroom Hideaway, 3,127 square feet, starting at $712,990
• 7-bedroom Seashore, 3,286 square feet, starting at $731,990
• 8-bedroom Baymont, 4,034 square feet, starting at $816,990
• 9-bedroom Clearwater, 4,382 square feet, starting at $865,990
• 10-bedroom Clearwater Grand, 4,382 square feet, starting at $879,990

For many investors, the first instinct is to look at the lowest entry price. That is understandable, but Windsor Cay is a community where bedroom count may be one of the most important underwriting variables. The reason is simple: many community-level costs do not drop enough on the smaller homes to fully offset the lower revenue ceiling.

The Fee Stack You Need to Model

This is where Windsor Cay gets more interesting, and more demanding. Based on the reviewed materials, recurring community charges are made up of HOA dues and CDD assessments rather than a separate mandatory resort fee.

According to the Windsor Cay HOA handout, monthly HOA dues are:

• $455 for townhomes
• $457 for 5- to 7-bedroom homes
• $467 for 8- to 10-bedroom homes

The same handout says HOA dues include lawn care, landscaping and fertilizing, irrigation water and maintenance, 75-channel cable TV, 1GB unlimited internet, clubhouse access, daily trash pickup, and some townhome repainting and roofing.

The Windsor Cay Community Development District, created by Lake County Ordinance No. 2022-55, shows FY26 adopted gross per-unit annual assessments of:

• $457.64 for townhomes
• $625.93 for 5- to 7-bedroom single-family homes
• $738.12 for 8- to 10-bedroom single-family homes

Using those figures, the approximate annual HOA plus CDD totals are:

Those totals are before property taxes, insurance, mortgage costs, utilities, pool care, cleaning, repairs, supplies, and management. In other words, Windsor Cay is not a low-fee ownership model. You should underwrite it like an operational hospitality asset, not a passive long-term rental.

Transient Taxes Matter More Than Many Buyers Expect

For short stays in Florida, the tax stack is meaningful. Florida imposes a 6% transient rentals tax on stays of six months or less. Lake County adds a 1% discretionary sales surtax and a 4% tourist development tax on transient rentals of six months or less.

That means a taxable short-term stay in Windsor Cay carries a combined occupancy-tax load of roughly 11% before platform fees. That is a major line item in your revenue model, and it needs to be accounted for upfront.

A bona fide written lease longer than six months falls outside that transient-rental tax regime. For most Windsor Cay buyers, though, the focus is vacation-rental income, so the short-stay tax structure is the one that matters most.

Why Bigger Homes May Underwrite Better

One of the more useful takeaways from the Windsor Cay pricing and fee structure is that larger homes may absorb overhead more efficiently. That is an inference based on the published home mix and fee structure, not a guarantee of stronger returns.

Still, the math is easy to understand. If your HOA and CDD costs are only modestly higher on an 8- to 10-bedroom home than on a smaller product, the larger home may have more room to spread fixed overhead across higher nightly revenue potential. That does not automatically make the biggest home the best buy, but it does mean the lowest purchase price may not be the strongest value.

This is especially relevant in a destination market that attracts large-family and multigenerational travel. Windsor Cay’s amenity package, private pools, and larger floor plans all align with that use case.

A Smarter Way to Underwrite Windsor Cay

If you are evaluating Windsor Cay seriously, build your model with conservative assumptions. Do not rely on builder marketing alone or assume strong occupancy every month of the year.

A practical framework should include:

• Purchase price and financing terms
• HOA dues and exact CDD assessment for the homesite
• Property taxes and insurance
• Utilities, including electric and water
• Pool service and routine maintenance
• Cleaning costs per turn
• Supplies, restocking, and minor repairs
• Booking or management fees
• The roughly 11% transient tax stack on short stays
• Revenue stress testing for slower periods

Your profit is usually won or lost in the gap between gross bookings and the full operating load. In a community like Windsor Cay, it is easy to focus on headline nightly rates and overlook the friction in the middle.

Questions to Ask Before You Write an Offer

Before moving forward, ask for the details that can change your numbers or your operating flexibility. A thorough review should include:

• The current HOA estoppel
• The FY26 CDD assessment for the exact homesite
• Any one-time capital contribution, working-capital, transfer, or application fees
• A clear list of owner-paid items versus included services
• Confirmation on whether pool service, pest control, linens, or guest amenity items are owner expenses
• The minimum-stay rules
• Owner-use rules
• Parking limits
• Pet rules
• Guest-registration requirements
• Confirmation of who collects and remits transient taxes
• Confirmation that the amenity package is complete for the phase you are buying into

That last point matters because Pulte states that community improvements and recreational features are based on current development plans and may change without notice. When you are buying for guest appeal, amenity delivery is part of your investment story.

Windsor Cay’s Real Strengths and Risks

Windsor Cay looks strongest as a purpose-built vacation-rental asset for larger groups near Orlando’s demand base. Its edge comes from new construction, private heated pools, and a resort-style amenity package that is designed for leisure travelers.

Its risks are just as clear. Fixed community fees are real. Transient taxes are high enough to affect margins. Operations can get complex fast once you add management, cleaning, maintenance, and turnover costs.

That does not make Windsor Cay a weak investment. It just means you should evaluate it with discipline. The best opportunities here are likely the homes that balance purchase price, bedroom count, and operating efficiency in a way that fits your hold strategy.

Final Takeaway for Investors

If you are comparing Windsor Cay to other vacation-rental options in the Orlando area, think beyond the brochure. Focus on net performance, not just gross revenue potential. In this community, the homes that look more expensive on day one may actually deserve a harder look if they spread fixed costs more efficiently and fit the large-group traveler profile better.

For many investors, Windsor Cay will make the most sense as a data-driven, purpose-built short-term rental play, not as a low-maintenance ownership option. If you go in with realistic assumptions, clear cost verification, and a sharp understanding of how each floor plan performs, you will be in a much stronger position to choose the right asset.

If you want help comparing Windsor Cay floor plans, reviewing fee structures, or evaluating whether a specific home fits your investment goals, Andrea Alonso can help you navigate the opportunity with a concierge, investor-focused approach.

FAQs

What kind of homes are available at Windsor Cay in Clermont?

• Windsor Cay currently includes 5-bedroom townhomes and 5- to 10-bedroom single-family homes, with private heated pools in every home.

What are the HOA costs at Windsor Cay for short-term rental owners?

• The reviewed HOA handout lists monthly dues of $455 for townhomes, $457 for 5- to 7-bedroom homes, and $467 for 8- to 10-bedroom homes, and notes that fees are subject to change.

What does the Windsor Cay HOA include for owners?

• The HOA handout says dues include lawn care, landscaping and fertilizing, irrigation water and maintenance, 75-channel cable TV, 1GB unlimited internet, clubhouse access, daily trash pickup, and some townhome repainting and roofing.

What are the CDD assessments at Windsor Cay?

• The FY26 adopted budget materials show annual gross per-unit CDD assessments of $457.64 for townhomes, $625.93 for 5- to 7-bedroom single-family homes, and $738.12 for 8- to 10-bedroom single-family homes.

What taxes apply to short-term rentals in Lake County, Florida?

• For stays of six months or less, the reviewed sources indicate a roughly 11% occupancy-tax stack made up of Florida transient rentals tax, Lake County discretionary sales surtax, and Lake County tourist development tax.

Is Windsor Cay best for small or large-group vacation rentals?

• Based on the published home mix, amenities, and fee structure, Windsor Cay appears best suited to large-group and multigenerational leisure stays, though actual performance depends on the specific home and operating model.