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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SPECIAL OFFER! Special Fall and Winter Rates!!! November 1 - December 25

New Windsor Hills 4B/4B Villa - S/F Pool, Game Rm, Free WiFi, Privacy – Property 159156

  • Windsor Hills rental - villa, 4 bedrooms, sleeps 11, 4 bathrooms, resort, pool
  • $1,085 - $1,575/week
  • Calendar Last Updated On: Nov 24, 2009
Stay in our luxury 5 star Windsor Hills Villa for LESS than what it costs at many local hotels. After a busy day at the attractions, laze about the private...
SPECIAL OFFER! Luxury beautiful home South Facing Pool October 29 - February 28

Beautiful Luxurious Villa, 5bdrm/5bath, with heated South Facing Pool – Property 172598

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 12, 5 bathrooms, resort, town, pool
  • $1,400/week
  • Calendar Last Updated On: Nov 24, 2009
Located in a beautiful gated resort. Less than 2 miles to Disney World, 20 minutes to Sea World & Universal Studios. 1 hr drive to Coco Beach or Kennedy Space...

A True Dream House! 3 Kid's Theme Rooms! South Facing Pool – Property 237627

  • Windsor Hills rental - house, 5 bedrooms, sleeps 12, 5 bathrooms, resort, town, pool
  • Calendar Last Updated On: Nov 24, 2009
Grand Opening! Welcome to Ethan's Disney Dream House. The best 5 bedroom, 5 bathroom home with 3 themed rooms (Princess, Mickey and Our very special Starwars themed...

3 BR/ 3B Townhouse/ South-facing Pool/Free WI-Fi – Property 176694

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 6, 3 bathrooms, resort, rural, pool
  • $693 - $900/week
  • Calendar Last Updated On: Nov 24, 2009
Romantic, luxurious 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...

Disney Area Vacation Rental Five Bedroom Select Weeks $1,000 – Property 149758

  • Windsor Hills rental - house, 5 bedrooms, sleeps 15, 5 bathrooms, resort, pool
  • $1,000/week
  • Calendar Last Updated On: Nov 24, 2009
Beautiful new home 2 miles from Walt Disney World located in the 'Reserve' section of a 24 hour guard gated resort community.

Disney Area Vacation Rental 6 Bedroom Select Weeks Sale $1,099 – Property 170098

  • Windsor Hills rental - house, 6 bedrooms, sleeps 16, 4 bathrooms, resort, pool
  • $1,099/week
  • Calendar Last Updated On: Nov 24, 2009
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...

Disney 5 Minutes Away. 42' Hdtv. Free Calls + Wi-Fi. Playstation 3. – Property 176042

  • Windsor Hills rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, resort, pool
  • $630 - $945/week
  • Calendar Last Updated On: Nov 24, 2009
Disney World is only a five-minute drive away from our first (ground) floor luxurious 3 bed 2 bath condo on Windsor Hills. Our 1412 sq ft home (one of the largest on...

Best Family Resort..Perfect Location..Call Me to Deal! – Property 158818

  • Windsor Hills rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, downtown, resort, pool
  • $665/week
  • Calendar Last Updated On: Nov 24, 2009
Bunk Beds & Disney Room for the Kids! Call Me to Deal! If you're looking for the Perfect location for your family vacation, This is it!

7817 Beechfield Street – Property 88239

  • Windsor Hills rental - house, 6 bedrooms, sleeps 12, 4 bathrooms, adventure, dish washer
  • Calendar Last Updated On: Nov 24, 2009
This beautiful 5 Star home is located in the community of Windsor Hills. This home features 6 bedrooms, 4 bathrooms (one of which has a garden tub) and will...

7821 Beechfield Street – Property 88240

  • Windsor Hills rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, adventure, dish washer
  • Calendar Last Updated On: Nov 24, 2009
This lovely single-storey home is situated in the community of Windsor Hills and will make your vacation very enjoyable. This beautifully decorated home features a...

7737 Teascone Blvd – Property 88429

  • Windsor Hills rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, adventure, child's highchair
  • Calendar Last Updated On: Nov 24, 2009
This home has such a personal atmosphere to provide comfort and welcome guests with its single level floor plan, individual touches in the décor and added amenities.

7739 Teascone Blvd – Property 88430

  • Windsor Hills rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, adventure, dish washer
  • Calendar Last Updated On: Nov 24, 2009
This beautiful home is situated in the community of Windsor Hills and will be a treat for your family and guests! This home has 4 bedrooms, 4 bathrooms and a sofa...

Luxury Windsor Hills Florida villa minutes from Disney sleeps 10 - 7753 Grassendale – Property 417744

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 10, 4 bathrooms, resort, private pool
  • $1,120 - $1,540/week
  • Calendar Last Updated On: Nov 24, 2009
Privately owned luxury villa just 10 minutes walk to Windsor Hills Resort clubhouse sleeps up to 10 adults/children: ideal for two families sharing.
SPECIAL OFFER! 2009 Year End Special: $1,500/week October 15 - December 31

Chelsea: Gm Rm, 55-in HDTV, WiFi – Property 157092

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, resort, pool
  • $1,500 - $1,900/week
  • Calendar Last Updated On: Nov 23, 2009
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.
SPECIAL OFFER! Introductory offer: Up to 30% off rates! October 8 - September 30

New luxury villa 2 miles to Disney w/ theme rms, game room, south facing pool. – Property 250801

  • Windsor Hills rental - villa, 6 bedrooms, sleeps 14, 4 bathrooms, resort, town, pool
  • $1,300 - $2,100/week
  • Calendar Last Updated On: Nov 23, 2009
Welcome to our new six bedroom, non-smoking, private vacation home in Windsor Hills Resort. This 5-Star resort community is also the closest to Walt Disney World-...

Beautiful 5 Bedroom/5 Bath Pool Home in Windsor Hills, 2 miles from Disney – Property 186004

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, resort, pool
  • $1,540 - $2,394/week
  • Calendar Last Updated On: Nov 23, 2009
Located in the fabulous Windsor Hills Reserve, a gated resort community, 'Sunset Ridge' has everything that you and your family or friends need for the most magical...

Exceptional pool home 2 miles from Disney, Game Room, Internet south facing pool – Property 187503

  • Windsor Hills rental - house, 6 bedrooms, sleeps 16, 4 bathrooms, resort, pool
  • Calendar Last Updated On: Nov 23, 2009
Gorgeous 6 Bedroom, 4 Bath home in the fabulous gated community of Windsor Hills less than 2 miles from Disney. This magnificent home sleeps 15 with 2 King-size...

Luxury South Facing Villa 5BR/5B in Windsor Hills, FREE Wifi, Game room! – Property 246139

  • Windsor Hills rental - villa, 5 bedrooms, sleeps 12, 5 bathrooms, resort, town, pool
  • $1,260 - $2,030/week
  • Calendar Last Updated On: Nov 23, 2009
Beautiful, South Facing Villa at Windsor Hills Reserve. Windsor Villa has everything that you and your family could possibly need for a magical vacation to Disney...

Luxury 5BR Pool Home 2.5 miles to Disney, Free Wifi, Gameroom – Property 242120

  • Windsor Hills rental - house, 5 bedrooms, sleeps 10, 5 bathrooms, town, pool
  • $1,540 - $1,730/week
  • Calendar Last Updated On: Nov 23, 2009
Tropical Sun is a beautiful vacation home located in the fabulous Windsor Hills Reserve, a gated resort community, less than 2.5 miles from Disney World.

Quality Villa w/pool, premium location in 5* resort, minutes to Disney – Property 144713

  • Windsor Hills rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, resort, pool
  • $775/week
  • Calendar Last Updated On: Nov 23, 2009
Greetings from Sydney's Point! Our Townhouse with private pool is ideal for all your Florida Vacation needs. Families will enjoy the easy access to Disney World...
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