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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Luxury for You, Fun for the Whole Family! 3BR/3BA Townhome Near Disney – Property 3015904

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, accept credit card, Private Pool
  • Calendar Last Updated On: Jun 18, 2013
We bought this home in May 2012 because we were vacationing at least once a year in Orlando and wanted a place that had the comfort of a high-end hotel but the...

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: Jun 18, 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.

5 Bed Windsor Hills Pool Home – Property 3488157

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, wheelchair accessible, Resort
  • Calendar Last Updated On: Jun 18, 2013
This magnificent 5 bed, pool home offers a great “bang for your buck” on your next vacation! Not only is this house located in the fabulous five star Windsor Hills...

NEW 5 STAR DISNEY THEMED VACATION HOME WINDSOR HILLS SOUTH FACING POOL – Property 324749

  • Windsor Hills rental - house, 6 bedrooms, sleeps 12, 4 bathrooms, accept credit card, wheelchair accessible
  • $2,395 - $3,595/week
  • Calendar Last Updated On: Jun 18, 2013
This new home in Windsor Hills is flat out awesome. We decorated and outfitted it ourselves. We put things in this home that we put in our own house including top of...

DELUXE 5 BED 5 BATH VACATION PARADISE – Property 328071

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, accept credit card, wheelchair accessible
  • $2,495 - $3,295/week
  • Calendar Last Updated On: Jun 18, 2013
AMAZING VACATION HOME WITH ALL THE COMFORT OF HOME AND THEN SOME. SPOIL YOURSELF AND YOUR FAMILY FOR YOUR NEXT VACATION. YOU WILL LOVE IT!!! Two master King suites...

Disney Townhouse Brand New Free VIP Passes . Only 1 mile to Disney – Property 202225

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, Resort, Private Pool
  • Calendar Last Updated On: Jun 18, 2013
We have a beautiful brand new townhouse located in the 5 star gated community Windsor Hills, this community is just 1.5 miles from Disney closer than many of...

Luxury Home with South Facing Pool -Air-Conditioned Game Room- 2 miles to Disney – Property 237163

  • Windsor Hills rental - house, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, Resort, Town
  • $1,505 - $2,030/week
  • Calendar Last Updated On: Jun 18, 2013
This home was finished in May 2009! Our luxury home is situated in the 5 star resort community of Windsor Hills in Kissimmee, Florida.

Newly Decorated Luxury Villa/Windsor Hills Community-New Tile on Main Level – Property 185961

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, Resort
  • $1,375 - $2,150/week
  • Calendar Last Updated On: Jun 18, 2013
SPECIAL PRICING FOR 2013: Sept. THRU Mid Dec. AND FOR 2014 Jan THRU March $1279/week FREE POOL HEAT OCTOBER THRU APRIL (with a weekly rental) *Brand new tile on...

Great rates! 1.5 Miles to Disney - Luxury 3BR/3BATHs Townhome w/Pool - Sleeps 8 – Property 159233

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, accept credit card, Resort
  • $693 - $840/week
  • Calendar Last Updated On: Jun 18, 2013
5* Resort - Luxury Townhome: 3 Bedrooms, 3 Baths, heated Splash pool (sleeps 8) in the Windsor Hills Resort. FREE WIFI, local & long distance calls.

WINDSOR HILLS LUXURY 3BR 3BA PRIVATE POOL TOWN VILLA - 1.5 miles to Dsny – Property 246855

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, accept credit card, Resort
  • $845 - $1,085/week
  • Calendar Last Updated On: Jun 18, 2013
Welcome to your by owner direct deluxe Windsor Hills vacation rental pool home, MICKEY’S MAGICAL ESCAPE. Located in the heart of the vacation capital of the world,...

Disney Haven: a Luxury Townhome in the Windsor Hills Resort – Property 369086

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 6, 3 bathrooms, Private Pool, Air Conditioning
  • Calendar Last Updated On: Jun 18, 2013
This luxurious and fully furnished 3 bedroom and 3 bathroom townhome with a private heated splash pool is in the serene community of the Windsor Hills Resort - a...

Special Discount - Limited Time- Luxury Villa- New Game Rm !! – Property 175799

  • Windsor Hills rental - house, 6 bedrooms, sleeps 14, 3 bathrooms, 1 half bath, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Jun 18, 2013
Take advantage of our Special discount being offered for a limited time of 30% discount off our regular rates. Taxes of 13% will be applied to all reservations.

Child Friendly-Mickey Mouse House of Fun- POOL-2 miles to Disney -Windsor Hills – Property 194239

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, accept credit card, Resort
  • Calendar Last Updated On: Jun 18, 2013
Windsor Hills Resort townhouse only 2 miles from Disney World's main gate. 5-star luxury resort. 3 bedrooms and 3 bathroom townhouse very close to clubhouse w/...

Fabulous Lake View/South Facing Pool Home - 2 Miles to Disney! – Property 326849

  • Windsor Hills rental - house, 5 bedrooms, sleeps 12, 5 bathrooms, Lake, Private Pool
  • Calendar Last Updated On: Jun 18, 2013
Best Location & Lake Views: Our stunning 5 bedroom/5 bathroom villa has South Facing Pool and beautiful Lake Views and is located in the 5 star gated/guarded resort...

!!! Special Price !!! Through- May 2013 Chelsea: Gm Rm, 55-in HDTV, WiFi – Property 157092

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, accept credit card, Resort
  • Calendar Last Updated On: Jun 18, 2013
Enjoy a 55 inch big screen HDTV & 9 TV/DVD players in the home. Air-condition game room w/ pool table, air hockey, play station 2 & foosball table.

Windsor Hills - Congratulations on your choice of resorts!!! – Property 258562

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Jun 18, 2013
Windsor Hills will impress you! It is the newest, finest, most enjoyable community in Kissimmee! The amenities are just awesome for kids and adults alike.

Luxury 5 BR pool villa, closest to Disney, closest to the Clubhouse! – Property 326911

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 12, 5 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Jun 17, 2013
Enjoy your family vacation at our family owned, luxury 5-bed 5-bath Villa Aqua with private pool and spa at the Windsor Hills resort near to Walt Disney World in...

6bdr luxury home with south facing pool EXTENDED pool deck close to clubhouse – Property 372303

  • Windsor Hills rental - house, 6 bedrooms, sleeps 12, 4 bathrooms, accept credit card, Resort
  • $1,120 - $1,400/week
  • Calendar Last Updated On: Jun 17, 2013
Stunning 6 Bedroom 4 Bath Home with, South Facing Pool in Highly Sought after Windsor Hills Resort. This house is only ONE of a handfull with an EXTRA LARGE pool...

6 BR 2 Miles To Disney $1,299 Per Week With No Cleaning Fee – Property 170098

  • Windsor Hills rental - house, 6 bedrooms, sleeps 12, 4 bathrooms, accept credit card, Resort
  • $1,299/week
  • Calendar Last Updated On: Jun 17, 2013
Our 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 lanai...

Well Appointed Luxury in Windsor Hills Resort 3 miles from Disney! – Property 901078

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 10, 5 bathrooms, accept credit card, Resort
  • $1,183 - $1,953/week
  • Calendar Last Updated On: Jun 17, 2013
Tropical Haven Villa is located in the 5 star resort of Windsor Hills, this 5 bed 5 bath villa is perfect for privacy as each bedroom has it`s own bathroom.
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