Windsor at Westside Resort
One of Central Florida's finest gated resort communities — luxury vacation homes minutes from Walt Disney World and all major attractions. A Resort dedicated to Short-Term Rentals.
Why Buy a Home in Windsor at Westside
Exclusive Resort Benefits
Windsor at Westside Resort is a premier vacation destination in Kissimmee, Florida, offering dedicated vacation homes, family resort amenities, and convenient access to Walt Disney World, Universal Orlando Resort, and other top Central Florida attractions. Homeowners and their guests can enjoy a resort-style pool, lazy river, splashpad, fitness center, sports courts, and family-friendly entertainment, making it an ideal choice for family vacations, group getaways, and extended stays near Orlando.
Residents and guests enjoy access to a stunning clubhouse, resort-style pool and splash zone, fitness center, sports courts, and a dedicated on-site management team. Ownership is completely hands-free if desired.
Property in Windsor at Westside starts in the high $400's
ABOUT THE COMMUNITY
Massive Clubhouse and Waterpark
Enjoy the aerial view of the Clubhouse Amentiies
PHOTO GALLERY
Explore the Resort, Home Models and Floorplans
Featuring 6-9 Bedroom Pool Homes and 4 - 5 Bedroom Townhomes with pools and a one car garage
Why buy a home in Windsor at Westside?
Owning a piece of Windsor Island may be rewarding. This Vacation Rental Resort was built specifically for the short-term investment. This is a master-planned Resort with ideal floorplans such as thought out bed to bath ratios, open floorplans, multiple living areas, shaded patios, inground swimming pools and spas and all the comforts of home. Enjoy the ownership of a vacation home investment by offering guests all the conveniences of home, plus luxuries they wont find home. Windsor at Westside is really a fantastic Resort and a great option for your investment.
PROPERTY FEATURES
Everything You Need
World-class amenities, resort-quality finishes, and a location guests love — everything you need for a successful vacation home investment.
Resort Pool Complex
Zero-entry lagoon pool, splash pad, jacuzzi spa, lazy river, and poolside cabanas — open year-round.
Clubhouse & Game Zone
Full clubhouse with arcade, billiards, community gathering rooms, and concierge services.
Fitness Center
State-of-the-art equipment, yoga studio for all residents and guests.
VolleyBall Court
Beach Sand Courts
Restaurant
Casual Fare and Bar located On-Site
Sport Courts
Basketball and Soccer
Where is Windsor at Westside Located?
Mobile App
Download our App and Search for Homes in Real Time!
Our unique app is available for iphone or android. It allows you the freedom to search anytime at your convenience. Listings are available live just as I see them so there are not delays like you find on those national websites.
“This app is so easy to use” — D. Stewart - Kissimmee, FL
Enjoy features like:
Search by Location using our Map Search
Numerous Search Filters to pinpoint your preferences
Specific information pertaining to each home
Search Homes on Our App
Mobile App
Download our App and Search for Homes in Real Time!
Our unique app is available for iphone or android. It allows you the freedom to search anytime at your convenience. Listings are available live just as I see them so there are not delays like you find on those national websites.
“This app is easy to use” — F. Johnson - Boston, MA
Enjoy features like:
Search by Location using our Map Search
Numerous Search Filters to pinpoint your preferences
Specific information pertaining to each home
CLARITY
Common Questions
How frequently are HOA fees collected?
Assessments are typically billed and collected on a monthly basis. Statements are distributed approximately 30 days prior to the due date, ensuring owners have ample time to process their payments.
How can I buy a home in Windsor at Westside Resort?
Buying a home in Windsor at Westside requires navigating short-term rental zoning, HOA guidelines, and local Kissimmee market values. To make the purchasing process seamless and secure the best property, contact use to get exclusive access to active listings and expert guidance.
Are there penalties for delayed assessment payments?
Yes. Payments received after the specified grace period are subject to a late fee. Additionally, interest may accrue on outstanding balances in accordance with the community's governing documents.
If I have rentals in my home will they have free, unlimited access to the Resort Amenities?
Yes, all guests have access even if the home owner is not present with them.
What types of services are included in the HOA fee?
basic internet and cable tv, groundskeeping, all clubhouse amenities except for restaurant, arcade and drinks, 24/7 Security Guarded Gate, Trash Pickup
What types of homes are available at Windsor at Westside
The community features 4-to-5 bedroom luxury townhomes and turn-key 6-to-9 bedroom single-family pool homes. Depending on your investment purpose, Home Sales near Disney can help you make a smart decision.
Matthew Montalvo, PA
Realtor
As a specialized real estate agent with La Rosa Realty, Matthew Montalvo provides unparalleled expertise in the Disney World area, helping clients find the perfect vacation home, residence or investment property. About Us
© 2026 Matthew Montalvo
La Rosa Realty 1420 Celebration Ave, Celebration FL 34747
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