"Holiday Realty made buying our Windsor Hills home effortless. Their knowledge of the resort and rental market is unmatched — we were booked solid within weeks."
Sarah & James M.
Bought a 5-bed in 2024
Short Term Rental Approved
KISSIMMEE, FLORIDA — 2.5 MILES FROM DISNEY WORLD
Windsor Hills Resort
Property For Sale
Your premier destination for luxury vacation homes near Orlando's theme parks. Over 25 years of trusted real estate expertise by Holiday Realty LLC.
25+ Years ExperienceForbes #1 Vacation CommunityGuard-Gated Resort
By the numbers
Windsor Hills at a glance
0+
Years of Expertise
Trusted Windsor Hills specialists
0.0 mi
To Disney World
Closest gated resort community
#0
Forbes Vacation Community
Ranked best near Orlando
0
Days of Rental Demand
Year-round Orlando tourism
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Find Your Perfect Property
Explore vacation homes, townhomes, and condos — all designed for strong rental income and family enjoyment.
About Windsor Hills Resort
Vacation homes, condos and townhomes at Windsor Hills Resort for sale have been highly regarded long before Forbes Investors named it the #1 vacation home community in the country. Located just 2.5 miles from Walt Disney World, this guard-gated resort community offers investors a range of properties designed to maximize rental potential while providing guests with an exceptional Orlando vacation experience.
With over 25 years of combined experience in the Central Florida vacation home market, Holiday Realty LLC is the most experienced short-term rental real estate brokerage specializing in Windsor Hills Resort. We assist buyers and sellers from all over the world.
The Holiday Realty Difference
Why Choose Windsor Hills?
A gated resort community in Kissimmee, Florida offering luxury living, strong rental returns, and unbeatable proximity to Walt Disney World.
Minutes from Disney World
Just 2.5 miles from Walt Disney World — the closest vacation home resort to Orlando's top theme parks.
World-Class Amenities
Resort clubhouse, pool, waterslides, movie theater, games room, fitness center, and more.
Guard-Gated Community
24/7 guard-gated security for peace of mind. A safe, family-friendly environment for residents and guests.
Earn Rental Income
High short-term rental demand near Orlando. Forbes' #1 rated vacation home community in the country.
World-Class Living
Resort Amenities You'll Love
Windsor Hills Resort features world-class amenities designed for unforgettable family vacations and relaxation.
- 24-hour guard-gated entry
- Resort-style pool & waterslides
- Movie theater
- Games room & arcade
- State-of-the-art fitness center
- Resort clubhouse
- Basketball & volleyball courts
- Walking & jogging trails
Unbeatable Location
Minutes from everything
Windsor Hills sits closer to Walt Disney World than any other vacation rental community in Central Florida.
Windsor Hills Resort
2600 N Old Lake Wilson Rd, Kissimmee, FL
- Walt Disney WorldClosest resort community7min
- Disney Springs12min
- SeaWorld Orlando18min
- Universal OrlandoEpic Universe in 202522min
- Orlando Premium Outlets14min
- Orlando Intl Airport (MCO)35min
Drive times are typical off-peak estimates from the Windsor Hills clubhouse.
Client Stories
Trusted by hundreds of owners
Real reviews from buyers, sellers, and investors who chose Holiday Realty.
"Sold above asking in under three weeks. The team's marketing photos and pricing strategy made all the difference. Truly the Windsor Hills experts."
Priya K.
Sold her Spencer in 2023
"We've used Holiday Realty for two purchases now. Honest, responsive, and they genuinely care that the property works as an investment, not just a sale."
The Rodriguez Family
Owners since 2019
"Buying internationally felt daunting until we worked with this team. Everything from inspection to closing was handled remotely with total transparency."
Mark T.
Investor, UK
"I cannot recommend them enough. They knew every floor plan inside out and matched us with exactly the right unit on the first showing."
Linda H.
Bought a Sonoma condo
"Smooth, professional, and refreshingly honest about pricing. The whole process took less stress than we ever expected."
David & Anna B.
Sellers, 2024
"Holiday Realty made buying our Windsor Hills home effortless. Their knowledge of the resort and rental market is unmatched — we were booked solid within weeks."
Sarah & James M.
Bought a 5-bed in 2024
"Sold above asking in under three weeks. The team's marketing photos and pricing strategy made all the difference. Truly the Windsor Hills experts."
Priya K.
Sold her Spencer in 2023
"We've used Holiday Realty for two purchases now. Honest, responsive, and they genuinely care that the property works as an investment, not just a sale."
The Rodriguez Family
Owners since 2019
"Buying internationally felt daunting until we worked with this team. Everything from inspection to closing was handled remotely with total transparency."
Mark T.
Investor, UK
"I cannot recommend them enough. They knew every floor plan inside out and matched us with exactly the right unit on the first showing."
Linda H.
Bought a Sonoma condo
"Smooth, professional, and refreshingly honest about pricing. The whole process took less stress than we ever expected."
David & Anna B.
Sellers, 2024
Frequently Asked Questions
Everything you need to know about Windsor Hills Resort vacation homes.
Let's Talk
Ready to Find Your Dream Vacation Home?
Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.