Windsor Hills Resort

Windsor Hills Resort is considered a premier vacation resort with first class resort amenities, located in Kissimmee, only 2 miles from Disney's main gate. This highly popular gated community features wide tree lined boulevards, pavements, street lighting and recreation areas - a safe environment for children of all ages, especially the zero entry beach style double Olympic sized community swimming pool.


Windsor Hills Resort is one of the closest vacation home communities to Walt Disney World, just minutes from the entrance to the parks. The location offers easy and fast access to all attractions, shopping malls and restaurants in the area. This enviable location allows you to spend your holiday enjoying your self rather than stuck in traffic on the US192.


Windsor Hills Resort is located closer to Disney World parks than some of Disney’s own “on site” resorts!! The fantastic location of Windsor Hills Resort allows you to visit the parks in the morning, come back for a dip in the pool and be back in the parks for dinner and fireworks.


If you would rather not drive at all why not use the regular and reliable shuttle service to take you to all of the local attractions. Windsor Hills allows you the ultimate flexibility to really enjoy your villa rental holiday. There is now a brand new Walmart Superstore within a 4 minute drive from Windsor Hills Resort making buying provisions very easy.


For detailed information about Windsor Hills Resort, please see our Windsor Hills Resort page 


1 to 8 of 8 Properties

  • Brentwood 4

    Fav Windsor Hills Resort Brentwood 4


    This luxurious no holds barred 6 bedroom 4 bathroom vacation villa features a large private pool WITH EXTENDED POOL AREA, spa, games room with pool table, electronic dart board and XBox, wireless high speed internet access, fully air-conditioned and TV's throughout and walking distance to Club House and Playground areas. Our villa offers you the best of both worlds for the entire family – it combines the five-star communal activities of Windsor Hills and a private holiday home with private pool and a covered lanai.

    From $260  View Details

  • Sonoma 1

    Fav Windsor Hills Resort Sonoma 1


    This beautifully decorated top floor (with elevator), top class Windsor Hills 3 bedroom 2 bath condo comes complete with all of the amenities for a home away from home feel. Complete with TV's in all rooms, newly added ceiling fans, and Wifi throughout. Stay tuned with cable TV, DVD and a selection of DVD's, books and board games for your pleasure. Walk to the amazing water park featuring duelling slides, loads of fun for kids of all ages. The kitchen is fully equipped, and the laundry area comes complete with full-size washer and dryer.

    From $150  View Details

  • Sheldon 4

    Fav Windsor Hills Resort Sheldon 4


    Your family will love their stay at Mickey's Magical Villa! Only 2 miles from Disney, your 5 Star vacation home is packed with state-of-the-art convenience to make your vacation comfortable and has all the fun stuff too.  High chair, pak 'n' play, bed rails, Quality kitchen appliances, washer and dryer.  50" Plasma TV, TV/DVD in each bedroom, private pool and spa, Games Room, Playstation 2, iPod dock, Radio/CD player system,  There is no shortage of fun !!

    From $215  View Details

  • Seville 1

    Fav Windsor Hills Resort Seville 1


    Attractive 5 bedroom 5 bathroom vacation villa only 2.5 miles from Disney and featuring a large south-facing private pool & spa, Games room with pool table, air hockey & PS4 games console, 52" LCD cable TV in the family room, LCD cable TV's in all bedrooms, wireless high-speed internet access & fully air-conditioned throughout.

    From $335  View Details

  • Brentwood 7

    Fav Windsor Hills Resort Brentwood 7


    Our 6 bedroom/4 bath luxury villa is located in the Reserve section of Windsor Hills on a corner lot. Superbly equipped with games room, flat screen TV's throughout, SONOS sound system making this a home away from home.  Here your family will create memories that will last a lifetime! 

    From $230  View Details

  • Brentwood 5

    Fav Windsor Hills Resort Brentwood 5


    This luxurious 6 bedroom 4 bathroom vacation villa features a large privately screened south facing pool & spa with NO rear neighbors, games room, X-Box 360 & PS2, high speed internet access, free phone calls anywhere in the world, central air-conditioner/heater, Disney themed bedrooms, cable & TV in all rooms, large TV in living room, and walking distance to Club House and Playground areas.  

    From $245  View Details

  • Brentwood 6

    Fav Windsor Hills Resort Brentwood 6


    This luxurious updated no holds barred 6 bedroom 4 bathroom vacation villa features a large private pool, spa, games room, PS2, wireless high speed internet access, fully air-conditioned and LCD TV's in every bedroom, many with DVD's plus a 55" smart LCD TV in family room. The lanai has a wall mounted smart LCD TV and 2 ceiling fans adding to your poolside enjoyment.

    From $255  View Details

  • Brentwood 9

    Fav Windsor Hills Resort Brentwood 9


    Our stunning villa is perfect for families or groups seeking the ultimate in space, luxury, facilities and convenience. Fully updated in September 2018, south facing pool in a prime Windsor Hills location, across the street from the largest Windsor Hills playground and a short walk to the new splash pad and water slides! Professional photoshoot pending.

    From $260  View Details

8 Properties