Just Beyond the Main Event…Windsor Hills

First and foremost, staying in Windsor Hills means being near and dear to the vortex of fun that is Disney/Orlando, and the people wise enough to choose this as their home base will be met with convenience and comfort minus the crazy crowds that go along with being too close. You don’t have to stay in the park to properly enjoy it; so check out this vacation rental community with all the fixings.


In addition to it being a mere two-mile journey to the land of Disney (and there are shuttles available, by the way), you’ll also be pleased to know that Windsor Hills has plenty of little perks that will keep you and your companions happy campers even when you aren’t riding the rides and shaking hands with your favorite characters.


Located just off Highway 192, the road will take you to a number of restaurants and shopping centers in order to meet those typical, non-Disney vacation needs. Just in your own backyard however – literally – is a scene that will take all the stress out of your body. Lagoon-style swimming pools, mini-movie theatres, exercise facilities, game rooms, tennis courts, putting greens and more…these little details will just make life easier, ensuring that when you’re away from the park scene, you’ll still be living the good life.


Picking out a vacation rental specifically designed to meet every leisurely whim that you could imagine will be one of the most natural things you’ll ever do. If you’re planning to cross that bundle of theme parks off your list you might as well ensure the supreme comfort of everyone involved; thanks to places like Windsor Hills, there’s really no reason not to.

Destination: Search

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Vacation Rentals in Windsor Hills

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Luxury Condo with Lake View 1.5 Miles from Disney – Property 200833

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: May 18, 2013
Luxury second floor condo with one of the best locations on the Windsor Hills resort - directly overlooking the lake, but just steps from the pool gate and clubhouse...

DSNYs Retreat - An Elegant pool home on Windsor Hills – Property 174437

  • Windsor Hills rental - house, 5 bedrooms, sleeps 11, 5 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: May 17, 2013
This home has been individually furnished, decorated window dressed and upgraded. There are sofas and love seats in the lounge, a 50' TV with cable + wifi high-speed...

Get 1 Free Night@ Disney Getaway in Windsor Hills - 5 BR/5 BA – Property 336389

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 10, 5 bathrooms, accept credit card, limited accessibility
  • $1,110 - $2,023/week
  • Calendar Last Updated On: May 17, 2013
Get 1 free night for stays of 7 nights or longer at Disney Getaway, our luxurious five bedroom, five bath home in the upscale vacation resort community of Windsor...

Grand Opening - 7 BR 4 Full Bath Luxury Villa at Disney's Doorstep – Property 3002269

  • Windsor Hills rental - house, 7 bedrooms, sleeps 18, 4 bathrooms, accept credit card, Private Pool
  • $1,380 - $2,080/week
  • Calendar Last Updated On: May 17, 2013
Completely refurnished and professionally decorated in October 2012, this executive villa is situated on a large corner lot in prestigious guard gated resort...

Windsor Hills - Stuning Executive Villa – Property 268588

  • Windsor Hills rental - house, 5 bedrooms, sleeps 12, 3 bathrooms, 1 half bath, Resort, Private Pool
  • $1,190 - $2,000/week
  • Calendar Last Updated On: May 17, 2013
Less Than Two Miles From Disney, 'Stunning Executive Villa has everything that you and your family could possibly need for the most magical vacation to Disney and...

2576 Archfeld Blvd – Property 3016484

  • Windsor Hills rental - condo, 6 bedrooms, sleeps 12, 4 bathrooms, Television
  • $2,681 - $3,626/week
  • Calendar Last Updated On: May 17, 2013
Floor Plan (Brentwood) - 2,812 sq.ft. 2 story home with pool and spa (North-West Facing Pool) We invite you to enjoy our home on your next trip to Orlando.

2 Miles from Disney,Themed RMs, South Facing Pool – Property 324839

  • Windsor Hills rental - house, 6 bedrooms, sleeps 15, 4 bathrooms, limited accessibility, Resort
  • Calendar Last Updated On: May 17, 2013
Exceptional 6 bedroom 4 Bath pool home in one of the most sought after gated resorts in the Disney area. Our villa is just 2 miles from Disney's main entrance making...

Brand New Villa Windsor Hills 3 miles to Disney South Facing Pool – Property 928569

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, Resort
  • $1,199 - $2,399/week
  • Calendar Last Updated On: May 17, 2013
Located in the gated and guarded resort community of Windsor Hills, only 2 miles from Disney. This privately owned executive 6 bedroom 4 bathroom vacation villa has...

No Rear Neighbors, and 2 kids theme rooms, plenty of space for family – Property 293069

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, wheelchair accessible, Resort
  • $1,500 - $1,700/week
  • Calendar Last Updated On: May 17, 2013
This is a well maintained 6 bedroom home in Windsor Hills resort. The furniture is in excellent condition. There are TVs and dvd players in all the rooms and in the...

Disney Dreamin' Townhouse at Windsor Hills with Mickey Room – Property 137331

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 7, 3 bathrooms, accept credit card, wheelchair accessible
  • $770/week
  • Calendar Last Updated On: May 17, 2013
Make your Disney Dreams a reality when you stay in our beautifully decorated, 3BR townhome, located in the gated community of Windsor Hills.

'Late Rate' May 26th - June 3rd 2013 Quote ' LR13' – Property 175219

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 12, 5 bathrooms, accept credit card, Resort, Town
  • Calendar Last Updated On: May 17, 2013
2 Miles to Disney - Windsor Hills Resort is the nearest gated community to Disney property. Our home has 5 bedrooms and 5 bathrooms so all the family can vacation...

Royal Ascot - Luxury 5br/5ba Villa with Games Room, Pool, Free Wifi – Property 320925

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 12, 5 bathrooms, accept credit card, Resort
  • Calendar Last Updated On: May 17, 2013
Royal Ascot has everything that you and your family could possibly need for the most magical vacation to Disney and the attractions of Orlando.

Mickey and Friends themed 2 bed, 2 bath condo, Highspeed WIFI, PS3, Great Rates! – Property 316208

  • Windsor Hills rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Resort
  • $595 - $875/week
  • Calendar Last Updated On: May 17, 2013
Our 2 bedroom, 2 bathroom condo has a fabulous location only 3 miles from Disney. The condo has a wonderfully themed 'Mickey and Friends' family bedroom with 2 full...

Our Magical Retreat, Family Friendly, See our April Specials – Property 176005

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Resort
  • $775/week
  • Calendar Last Updated On: May 17, 2013
Located within the desirable Windsor Hills gated community, our condo is beautifully furnished and decorated to a high standard with all of the comforts of home.

Luxury 5 min. from Disney w/princess room,private pool,spa,pool table,Wii,Xbox – Property 270267

  • Windsor Hills rental - house, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, limited accessibility
  • Calendar Last Updated On: May 17, 2013
Grand Opening of our 6 bedroom 4 bathroom Disney Dream House. The largest most luxurious home in the 5 star gated resort of Windsor Hills!

15% May DISCOUNT – Property 902088

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, Communal Pool, Balcony
  • $618 - $791/week
  • Calendar Last Updated On: May 18, 2013
You will really enjoy this 3 bedroom 2 bath penthouse , 4th floor condo (the largest condo available in Windsor Hills resort) with a great view located in the...

2010, Windsor Hills, 6 Bed, Sth Face, Pool/ Spa, Free calls & Wi-Fi, Games Rm – Property 457341

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, wheelchair accessible
  • $1,310 - $2,124/week
  • Calendar Last Updated On: May 17, 2013
A Brand new 2010, '5' Star Luxury 6 bed, 4 bath fully air conditioned executive Villa in Archfeld Blvd with Free local, National & international call to over 40...

Serene Luxury Waterfront Disney Vacation Villa in Windsor Hills – Property 373571

  • Windsor Hills rental - house, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, Resort, Waterfront
  • Calendar Last Updated On: May 17, 2013
This Spectacular Waterfront Villa is located in the prestigious “Windsor Hills” gated community in Central Florida, featuring world class resort style amenities and...

Tinkerbells Retreat Disney Condo Next to Pool/Clubhouse – Property 172545

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Resort
  • Calendar Last Updated On: May 17, 2013
Why stay in a cramped hotel room when you can stay at our bright, spacious condo located in Windsor Hills Resort, newest gated community closest to Disney.

Windsor Hills 3 Bedroom Low Rates – Property 926226

  • Windsor Hills rental - apartment, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Resort
  • Calendar Last Updated On: May 17, 2013
Windsor Hills is a unique vacation home rental community that your family will enjoy time and time again. Some of the magnificent features of this 24-hour...
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