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  • The stunning Walt Disney Magic Kingdom lit up at night
    Closest to Disney - 2 miles from the gates of The Magic Kingdom
  • Windsor Hills Leisure Pool
    Windsor Hills Stunning Leisure Pool
  • Windsor Hills Club House
    The welcoming Windsor Hills Clubhouse
  • Jura Villa Luxury Master Bedroom

    Stunning Luxury Pool Villa minutes from clubhouse

    6 Bed 6 Bath Home...for details click here

  • Windsor Hills Olivers Oasis

    Luxury 3 Bed 2 Bath Condo

    3 Bed 2 Bath Condo...for details click here

  • Windsor Hills Sunkissed Villa

    SOUTH FACING POOL, Game Room, Themed Bedrooms

    6 Bed 4 Bath Home...for details click here

  • Windsor Hills Spiderman Themed Room

    1st Floor Condo; 2 minute walk to the pool!

    3 Bed 2 Bath Condo...for details click here

  • Windsor Hills Resort DSNYs Retreat

    Closest to the DSNY Magic

    5 Bed 5 Bath Home...for details click here

  • Windsor Hills Resort Executive Pool Home

    Stunning 5 Bed 5 Bath Executive Pool Home

    5 Bed 5 Bath Home...for details click here

Welcome to Windsor Hills Private Rentals - Luxury Villa Rentals in Orlando - Direct from Owner

Windsor Hills Resort Main Entrance

We're the newest and best Windsor Hills rental site. Rent direct from owners at Windsor Hills Resort, Kissimmee, Orlando. Get quotes now and begin planning your next dream disney vacation. 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 main pool with condo buildings overlooking

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 water slide and hot tub. 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

Windsor Hills Townhomes

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

Walt Disney World

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.

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Windsor Hills Pool

Windsor Hills Resort

Information on the Windsor Hills Resort in Kissimmee Orlando, just 2 miles from Disney.
Windsor Hills location in relation to orlando attractions and airports

Location & Directions

Find out where Windsor Hills is and how to get to all the major attractions with our location & directions guide.