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.

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Vacation Rentals in Windsor Hills

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Luxurious Executive 5 Bedroom 5 Bath Villa 2 Miles 2 Disney – Property 140814

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 10, 5 bathrooms, resort, town, accept credit card
  • $1,155 - $1,680/week
  • Calendar Last Updated On: Jul 19, 2008
Relax in luxury in our 5 bedroom 5 bath villa/home that has been professionally furnished to the highest of standards including 42' HD plasma TV with HD cable...

Mickey's Clubhouse At Windsor Hills Resort--Mickey Themed Deluxe Villa – Property 162616

  • Windsor Hills rental - house, 5 bedrooms, sleeps 12, 5 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 19, 2008
Continuing with the proud Disney themed tradition that we have established with Mickey's Condo, Hideaway, and Safari, Mickey's Clubhouse is a family owned, uniquely...
SPECIAL OFFER! July - August Discounted prices July 9 - August 31

July-Aug Special Luxurious 3 Bedroom Townhouse with Private South-facing Pool – Property 176694

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 6, 3 bathrooms, resort, rural, accept credit card
  • $693 - $1,043/week
  • Calendar Last Updated On: Jul 18, 2008
Luxury 3 bedroom 3 bath townhouse with spa pool is situated in the upscale 5- star resort of Windsor Hills which is an extraordinary gated vacation community set in...

Large High Qualilty Villa at Reasonable Prices – Property 177363

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, resort, town, accept credit card
  • $1,050 - $2,275/week
  • Calendar Last Updated On: Jul 18, 2008
This spacious and luxuriously decorated villa at Windsor Hills is well equipped and maintained to very high standards. Complete with pool, spa, games room and WiFi...

Mickey's World Theme Bedroom @ 5* Windsor Hills Resort – Property 193849

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, downtown, resort, accept credit card
  • $735 - $1,085/week
  • Calendar Last Updated On: Jul 18, 2008
Mickey's World 1 & 2 are professionally decorated and the kids will love their hand-made mickey & friends theme bedroom....please visit our web site to see...

Steps to Pool and Clubhouse - Luxury Condo at Windsor HIlls Resort – Property 154755

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 18, 2008
* New 3 bed 2 bath condo (sleeps 8) * Located only steps away from clubhouse and tropical landscaped pool area *Professionally decorated and furnished * Fully...

Affordable Luxury Close to all Disney Parks-Summer Specials – Property 157969

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, resort, town, accept credit card
  • $665/week
  • Calendar Last Updated On: Jul 18, 2008
The Kissimmee/Orlando area is the perfect destination for your next vacation. Everywhere you go there is entertainment for all ages.

Windsor Hills: Escape2disney - Luxury 2 Bedroom Condo – Property 191285

  • Windsor Hills rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, swimming pool, air-conditioning
  • Calendar Last Updated On: Jul 18, 2008
You will have a fun and relaxing vacation at your stay at the amazing Windsor Hills gated community. This condo is professionally and luxuriously furnished with all...

Luxury Windsor Hills 5 Bedroom Home w/ Free Car Rental – Property 181797

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, beach, resort, accept credit card
  • Calendar Last Updated On: Jul 17, 2008
This Magnificently decorated Villa offers you pure luxury! It provides every possible amenity you and your family could possibly need to fully enjoy your Orlando...

5 Star Windsor Hills Resort Pool Home, Closest to Disney – Property 124009

  • Windsor Hills rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, resort, town, accept credit card
  • Calendar Last Updated On: Jul 17, 2008
TV in EVERY room ! Windsor Hills has all the amenities of a 5 star hotel or resort but with the comfort, convenience and privacy of a home. Welcome to Florida's...

Luxury 4BR/ 4BA villa with pool & spa in Five Star Resort 2 miles from Disney – Property 170401

  • Windsor Hills rental - villa, 4 bedrooms, sleeps 10, 4 bathrooms, resort, swimming pool
  • $1,225 - $1,540/week
  • Calendar Last Updated On: Jul 17, 2008
Our vacation home has been professionally furnished to the highest of standards. This 4 bedroom pool home has an ample 2400 square feet of living space conveniently...

Windsor Hills Reserve - Brand New Luxury and Elegance-SW Facing Pool – Property 184615

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, lake, resort, accept credit card
  • $1,330 - $1,925/week
  • Calendar Last Updated On: Jul 18, 2008
Located less than 2 miles from Disney's gates. (Route 192 to Old Wilson Road, left into Windsor Hills) Situated on a premium lot in Windsor Hills Reserve, the...

Orlando Luxury 6 BR/4BA Home - Close to Disney - Game Room – Property 137702

  • Windsor Hills rental - house, 6 bedrooms, sleeps 14, 4 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 17, 2008
Looking for relaxation, fun, and a stress free vacation? Come and enjoy our beautiful, new 6 bedroom 4 bath home in Windsor Hills Resort, in Kissimmee, FL.

Exquisite 5 Star Condo Rates at $90/nt July Special – Property 140219

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 17, 2008
Located less than 2 miles from Disney and only a few exits from Sea World and Universal Studios. The Windsor Hills is a brand new 5-Star gated community offering...

Disney theme luxury 2BR/2BA condo with wireless hi-speed internet – Property 147018

  • Windsor Hills rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 17, 2008
The spacious living area opens to the lanai (balcony). The master suite has a king-size bed with its private bathroom. The second bedroom has two twin beds and a...
SPECIAL OFFER! Select Weeks $1199 In 2008 And 2009 June 25 - December 31

Brand New 6 Bedroom Home 2 Miles From Walt Disney – Property 170098

  • Windsor Hills rental - house, 6 bedrooms, sleeps 16, 4 bathrooms, resort, accept credit card
  • $2,250 - $2,750/week
  • Calendar Last Updated On: Jul 16, 2008
Our most luxurious vacation home has six bedrooms, four baths, a living, dining, family room and a kitchen with a breakfast room opening to a beautiful screened...
SPECIAL OFFER! Select Weeks $1,199 in 2008 And 2009 July 9 - December 31

New Five Bedroom, Five Bath Home 2 Miles From Disney World – Property 149758

  • Windsor Hills rental - house, 5 bedrooms, sleeps 15, 5 bathrooms, resort, accept credit card
  • Calendar Last Updated On: Jul 16, 2008
Beautiful new home 2 miles from Walt Disney World located in the 'Reserve' section of a 24 hour guard gated resort community.

Brand New 6 Bedrooms 4 Bathrooms Executive Home - August Special !!! – Property 191319

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 13, 4 bathrooms, resort, accept credit card
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Jul 16, 2008
Completed in May 2008, Florida Escape is a brand new 6 bed, 4 bath executive villa situated on the prestigious Windsor Hills Reserve only 2 miles from Disney's Main...

Fantastic First-Floor Condo - 5 Minutes to Disney. Free Phone and Internet. – Property 176042

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, resort, accept credit card
  • $630 - $945/week
  • Calendar Last Updated On: Jul 16, 2008
Disney is only a five-minute drive away from our first (ground) floor luxurious 3-bed, 2-bath home on Windsor Hills. Our 1412 sq ft home comes fully air-conditioned...

Luxury Condo, Steps To Pool. Disney 5 Minutes! – Property 153114

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, resort, accept credit card
  • $763 - $973/week
  • Calendar Last Updated On: Jul 18, 2008
Our low rates include taxes! Enjoy 3 large bedrooms, 2 spacious baths, fully equipped kitchen and laundry and 4 cable TVs, each with DVD for less than you would...
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