Windsor Hills Resort · Kissimmee, Florida

Your Family's Best Vacation
Starts the Moment You Walk Through the Door

Step into a private resort home complete with a water park, lazy river, and full kitchen — all just minutes from the world's most magical attractions.

View Available Homes Call (407) 973-2624
5 Resort-Style Pools
3 Mi. to Disney World
★ Top-Rated Homes
Luxury vacation home pool area at Windsor Hills resort

Resort-Style Living

Amenities That Feel Like a Vacation, Every Day

Windsor Hills isn't just a place to sleep — it's a full resort experience. While the theme parks close, your private paradise stays open.

Lazy River & Water Park

Float along the resort's lazy river or race down the water slides — right outside your door, with no admission fee.

Clubhouse & Fitness Center

Start your morning with a workout, then gather at the clubhouse lounge or game room for family time.

Private Home Theaters

Every home features a dedicated theater room with surround sound — perfect for movie nights after park days.

Game Rooms & Billiards

Each home includes a fully equipped game room with arcade games, billiards, and comfortable seating for the whole family.

Gated Resort Security

Rest easy knowing your family is safe in a 24-hour guarded, gated community with controlled access.

Full Gourmet Kitchens

Prepare family meals in spacious, fully equipped kitchens with premium appliances and dining for everyone.

Our Vacation Homes

Designed for Families Who Want More Than a Hotel Room

From spacious 3-bedroom cottages to grand 7-bedroom estates, every home at Windsor Hills is thoughtfully designed to give your family the space, comfort, and privacy of a real home — with all the luxury amenities of a five-star resort.

  • Private pool and spa with heated options
  • Dedicated game room with arcade and billiards
  • Themed bedrooms for children
  • High-speed WiFi and smart TVs throughout
  • Free dedicated parking for multiple vehicles
  • Weekly professional housekeeping included
Inquire About a Home (407) 973-2624
Spacious luxury living room in a Windsor Hills vacation home

Prime Location

The Perfect Base for Your Orlando Adventure

Nestled in the heart of Windsor Hills, our homes put you close to everything — without the crowds and hotel prices.

10
minutes
Walt Disney World
20
minutes
Universal Studios
15
minutes
SeaWorld Orlando
5
minutes
Orlando International Airport

Five Star Vacation Homes of Windsor Hills
2600 N Old Lake Wilson Rd, Kissimmee, FL 34747

Elegantly themed bedroom in a Windsor Hills vacation rental

The Guest Experience

Seamless from Booking to Check-Out

We handle every detail so you can focus on what matters — making memories with the people you love.

01

Bespoke Home Selection

Tell us about your group size and needs. We'll match you with the perfect home — no generic listings, just homes that truly fit your family.

02

Personalized Itinerary

Receive a curated guide to the area — restaurant recommendations, park tips, and local secrets you won't find in guidebooks.

03

Arrive & Unwind

Enjoy keyless entry and a home that's spotless, stocked, and ready. Your only decision is which pool to dive into first.

04

Concierge Support

Need groceries delivered? A crib for the little one? Our local team is just a call or text away, any time of day.

Reserve Your Stay

Your Dream Vacation Home Awaits

Whether it's a weekend getaway or a week-long Disney adventure, we have the perfect home for your family. Contact us today to check availability and secure your dates.

(407) 973-2624

We typically respond within 2 hours during business hours.

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