Welcome to the official rental website for the Windsor Hills Resort and its owners - Endorsed and run by the Resort Management Committee

We are the only way to secure your dream vacation rental in Windsor Hills Resort. All properties vetted by Resort Management. And no commission or booking fees. Our advanced search functionality is aimed at helping you find exactly what you are looking for.

The Resort

Find out why Windsor Hills is Orlando's most popular rental resort with our Windsor Hills Resort Guide...

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2 Miles from Disney

Perfectly located, find out where Windsor Hills is and how to get to all the major attractions with our location guide...

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Where to Stay

Advice on where to stay in the resort; closest to the tennis courts, clubhouse, pool or kids play area or in The Reserve...

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Property Options

Need a downstairs bedroom, review our extensive guide to all property styles and floorplans in Windsor Hills...

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Featured Properties


5 Bed Home

Affordable Luxury Holiday Townhouse

3 Bed Townhome

Princess, Pirate & Super Hero Themed Kids Bedrooms

6 Bed Home

Sunny Condo Retreat - Newly Renovated, New Listing

3 Bed Condo

Windsor Hill's Official Resort Rental Website

Our website is set up to provide the best outcomes for owners in the Resort and guests looking to visit. Fully endorsed by the Resort Management Committee all properties are vetted by Resort Management. Avoid the excessive commission and bookings fees of the major rental websites by securing your rental through Windsor Hills Private Rentals. Bookings are made directly with the owner/manager of the property of your choosing. Treat yourself to the perfect Florida vacation in the most popular resort community in the Orlando area – and the closest to the Walt Disney World Resort - only 2 miles from Disney. View our wide selection of Villas, Townhomes and Condos. Perfect for a family vacation, golf villa, business event, wedding or honeymoon, Windsor Hills Resort caters for every occasion. Enquire now, and speak direct to owners, for the best luxury vacation rental deals on Windsor Hills Resort.

Windsor Hills Resort Kissimmee Florida - Closest to Disney

Windsor Hills is a beautiful gated community just 2 miles (3km) from the gates of Walt Disney World. From comfortable condos and townhomes to spacious 4-bedroom,5-bedroom & 6-bedroom homes, you'll find accommodations to suit your every vacation need. The Windsor Hills Resort clubhouse features a huge lagoon-style pool complete with new water park facility. The resort offers a variety of recreation options & activities for all ages including children's playground, state-of-the-art fitness center, sand volleyball, basketball and tennis courts, 40-seat movie theatre, video arcade and billiards. It also offers a shuttle bus service to Walt Disney World, SeaWorld and Universal Studios (local charge applies).

Villas, Townhomes and Condos Available Now

All Windsor Hills rental villas feature a master suite with king or queen size bed, TV and a master bathroom with a garden tub and separate shower. Additionally, all of Windsor Hills home/villas have a private screened swimming pool with spa, and each townhome has a plunge pool. Homes are available with game rooms that include billiards, table tennis and air hockey along with play stations for kids. Unlike nearly all other resorts in the Orlando area the accommodations on offer cover all three main property styles: Villas, Townhomes and Condos serving all party sizes. The resort is adjacent to Mystic Dunes Golf course and 5 minutes from the main street shops and restaurants on US 192. Choose Windsor Hills Private Rentals for your perfect vacation rental property now.

Kissimmee Orlando Florida

Renting in Windsor Hills puts you smack bang in the centre of the theme park capital of the world as well as giving you easy access to a huge array of top quality golf courses most of which are competitively priced. The 4 largest theme park attractions (Walt Disney World, Universal Studios, Seaworld and Legoland) are all located in Kissimmee and thus within short driving distance from the Windsor Hills Resort. If it's golf you're after, all year round Florida sunshine makes Kissimmee the perfect base for a golfing holiday. Whether you power your drive 350 yards down the fairway or yell 'fore' before you even hit your shots you'll find the course for you in Kissimmee.