Windsor Island vs Windsor Cay (2026): The $100K Difference Investors Must Know!

If you're considering buying a vacation home near Disney for short-term rental income, understanding the difference between Windsor Island Resort and Windsor Cay Resort in 2026 is critical. In this video, I break down the real numbers investors are looking at right now, including resale opportunities versus new construction, furnishing costs, and why the approximately $100,000 price difference between comparable townhomes could significantly impact your overall return. We'll discuss: • Windsor Island vs Windsor Cay property prices in 2026 • New construction vs resale investment strategy • Furnishing costs for Orlando vacation rentals • Why Windsor Island resale homes may present unique value opportunities • HOA rule differences including 90-day vs 120-day usage • Real example of a 6-bedroom Windsor Island home priced below many new townhomes • Why Clermont and Davenport continue to attract vacation home investors Both resorts offer incredible amenities and are designed as sister communities, but depending on your investment goals, the numbers may lead you in different directions. As someone who has been involved with Windsor Island since its inception and has sold numerous homes in both Windsor Island and Windsor Cay, I regularly receive questions from investors comparing these two communities. This video shares my observations from the market in 2025 and what I’m seeing so far in 2026. If you're thinking about buying or selling a vacation home near Disney, positioning the property correctly in today’s market can make a significant difference. Contact me today to discuss current opportunities. View Windsor Island Homes For Sale https://www.homesneardisneyorlando.co... View Windsor Cay Homes For Sale https://windsorcayorlandoresort.com/h... Susan Benante REALTOR® RSPS, ABR, CLHMS, e-PRO Orlando’s Short-Term Rental Home Investment Strategist™ Powered by FATHOM REALTY 📞Call / Text: (407) 259-6211 📧 [email protected] Thank you for watching. Subscribe to my videos! 00:00 Introduction 00:35 2026 Update on Communities 01:23 About Windsor Cay 01:55 Why Windsor Cay new construction makes sense 02:25 Comparing amenities between both resorts 02:49 Investor purchases and home furnishing 03:00 My advice for buyers and sellers 04:09 Comparing Windsor Cay Townhomes and Windsor Island Townhomes 04:33 Pricing in Windsor Island right now 05:41 Windsor Cay HOA maximum stay rules 05:59 Windsor Island maximum stay rules 06:10 Final Summary 06:36 Buyers and Sellers at Windsor Cay and Windsor Island https://www.homesneardisneyorlando.com https://www.windsorcayorlandoresort.com https://www.thewindsorcayresort.com https://www.waterleigh.com #OrlandoRealEstate #VacationHomesForSale #DisneyAreaHomes #ShortTermRentalInvesting #OrlandoInvestors #AirbnbInvestment #FloridaRealEstate #LuxuryVacationHomes #RealEstateInvesting #DisneyVacationHomes   / susan-benante-realtor     / susan_benante_realtor     / susanbenanterealtor     / orlando_real_estate      / @susan_benante_realtor