Windsor Hills Resort

One of the closest gated resort communities near Walt Disney World. This Resort has earned the reputation of one of the greatest producing short-term rentals in the area.

Windsor Hills Resort AquaPark

Why Buy a Home in Windsor Hills Resort

Windsor Hills is amongst the original vacation home resorts with a proven track record of successful years in operation. This proven resort features 2 and 3 bed condos, 3 bed townhomes with splash pools and 4-6 bed pool homes. The 6 bed homes feature 3 en-suites, the 5 bed homes feature 3 and 4 en-suites depending on the floorplan and the 4 bed homes feature 3 en-suites.

The Windsor Hills Resort is packed with amenities like the Aquapark that features waterslides and kids splash pad, lagoon pool, fitness room, sports courts and more. This Resort was built with vacation rental as priority.

Property in Windsor Hills start in the $200's

ABOUT THE COMMUNITY

Massive Clubhouse and Waterpark

Enjoy the aerial view of the Clubhouse Amentiies

PHOTO GALLERY

Explore the Resort

From arrival to poolside sunset — explore what makes this community exceptional.

PROPERTY FEATURES

Resort Style Amenities that set Windsor Hills Apart

What truly distinguishes Windsor Hills from a standard vacation rental is its lineup of resort-caliber amenities, including:

Resort Pool Complex

A heated lagoon-style pool, perfect for year-round swimming. An Aquaventure Water Park for families with kids

Clubhouse & Game Zone

Full clubhouse with arcade, billiards, movie theater, ping pong tables and sundry shop

Fitness Center

State-of-the-art equipment, yoga studio for all residents and guests.

VolleyBall Court

Beach Sand Courts

On-Site Management Team

Support and Service throughout your stay

Sports Courts

Tennis Court, Basketball Court & Putting Green

Investment & Short-Term Rental

Ownership can also be entirely hands-free, freeing owners from the day-to-day demands of running a rental property themselves.

Having operated a vacation home management company for nearly 20 years, past guests would always leave positive feedback about the close proximity of Windsor Hills to Disney World and local dining and attractions. We didn't have any experience renting out the condos but for the townhomes guests would mention they liked that they had 1 bedroom on the first floor and the splash pools.

Regarding the single family homes, guests would leave positive feedback about the bed to bath ratio being great and a reason why they return along with the shaded lanais. Something frequent we heard that was frustrating at times to the renters, was the strict security. We found that to be a good thing for the homeowners.

2 Bed 2 bath Condo

from the $200's

3 Bed 2 bath Condo

from the $200's

3 Bed 3 bath Townhome

from the high $300's

4 bed 4 bath

from $500's

5 bed 5 bath

from the $600's

5 bed 5 bath

from the $600's

6 bed 4 bath

from the $600's

Where is Windsor Hills Located?

2600 N Old Lake Wilson Rd, Kissimmee, FL 34747, USA

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

Home Sales near Disney Mobile 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

Home Sales near Disney Mobile app

CLARITY

Common Questions

How frequently are HOA fees collected in Windsor HIlls?

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.

Can I own a vacation home in Windsor Hills Resort and rent it to the public?

Yes, Windsor Hills is zoned for short-term rental usage and is well known to the public that is strictly a vacation home resort.

If I have friends or guests 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 at Windsor Hills?

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 Property does Windsor Hills Resort offer?

Windsor Hills features 2 and 3 bedroom condos, 3 bedroom townhomes with splash pools and 4-6 bedroom Single Family Homes with Pools

How far is Windsor Hills Resort from DisneyWorld?

about a 10 minute drive to the park entrance, it is literally one of the closest Resorts to the Magic.

Are there a limited number of days I can rent out my home in Windsor Hills?

No, vacation rentals in Windsor Hills Resort can be rented year round with no limits.

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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