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Windsor Hills Holiday Rentals

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    1 / 61
    5 of 5 stars (9) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    1 / 54
    5 of 5 stars (5) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    1 / 30
    5 of 5 stars (53) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 11
    5 of 5 stars (11) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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    • x
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    About this property
    Windsor Hills is an oasis only a mile from Disney World. Amenities include a huge pool with a water slide, clubhouse, playgrounds, exercise room, putting green, sports area, convenience store and shuttles to major attractions. AAA gives it a 3 diamond rating and units are in high demand. Our... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 5 weeks ago
    We have never rented a condo, so this was a new venture for us. In the past, we've stayed on Disney property, which is totally cramped and overpriced. When we stepped in to the...
    4 of 5 stars Reviewed 12 May 2016
    This was a very nice condo and property, the pool and extra facilities were very nice also. Would have been nice to have ceiling fans to help circulate the air, even though the...
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    1 / 45
    5 of 5 stars (19) Excellent
    3 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
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    About this property
    GREAT NEWS! We've added Disney Dreams Too! It’s identical to Disney Dreams and is right next door. Now taking reservations for vacation dates ==>Website Disney Dreams Vacation Rentals .c o m Disney Dreams Vacation “is a spacious Orlando vacation town home in the heart of the exclusive Windsor... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 2 December 2015
    My family and I (5 and 7 year old children, hubby and I) just returned from a 6 night stay at Disney Dreams. Have nothing but fantastic things to say about Brandie, Disney...
    5 of 5 stars Reviewed 3 September 2014
    Stayed 12 nights in August with partner and daughter. All communication with owner Brandi beforehand was straightforward, she was very helpful with questions and responded...
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    1 / 76
    5 of 5 stars (74) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    YOUR ATTENTION PLEASE ! FLIPKEY / TRIP ADVISOR is frequently failing to notify us of incoming messages. Additionaly,whenever we get one, our replies are not reaching prospective guests. So, if you message us and don´t get an answer, please try to contact us outside here. The property title is the... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 2 July 2016
    Our stay was amazing. The last two times that we stayed in Orlando, we stayed right on Disney property. While that was great and all(hey, there are a couple of perks), this was...
    5 of 5 stars Reviewed 1 May 2016
    This is our second stay here (our last was June 2013), and once again, a huge thank you to Leila who throughout the entire process from our original booking enquiry to our arrival...
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    1 / 24
    4.5 of 5 stars (13) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Children's Pool
    • Hot Tub
    • Satellite TV
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Brand new 2010, '5' Star Luxurious 6 bed, 4 bath fully air conditioned executive Villa in Archfeld Blvd, Windsor Hills Resort, with Free local, National & international call to over 40 destinations & free wireless internet. You also have your own private heated Pool & Spa, Gas BBQ (Grill) The... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 16 June 2016
    We loved the home! Swimming pool and hot tub was a plus. Both had crystal clear water. It was in a good neighborhood.The people taking care of it could not be anymore...
    5 of 5 stars Reviewed 10 May 2016
    My family and I had a brilliant time and probably the best holiday of a life time. The house is amazing, very clean and with everything we needed. The children loved being so...
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    1 / 27
    5 of 5 stars (14) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
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    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Windsor Hills townhome has 3 bedrooms, 3 bathrooms, and it's own private splash pool. Windsor Hills is a gated community only 2 miles to the Disney World gates and is a convenient location for all of the area attractions. The home is decorated tastefully and up to date with the amenities... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 11 December 2013
    Found the townhome to be clean and well kept and enjoyed the lanai and pool. Also enjoyed the large flat screen TV in living room area. Conveniently located to Disney theme parks...
    5 of 5 stars Reviewed 5 December 2013
    When I enetred the house I found everything clean and tidy. Everything was perfect and exactly as the owner told me. I absolutly recommend it. The house is very confortable and...
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    1 / 26
    4.5 of 5 stars (5) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Truly the "K i n g" of all Luxury Vacation Resorts near Disney, our Windsor Hills Villa is located only 3 from Disney's Main Gate. Within 1 mile of our Windsor Hills villa lies a vast sea of shops, supermarkets, stores, entertainment, and activities. Our Windsor Hills Resort community is a 24... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 12 July 2016
    This house was just so wonderful and the interior was beautiful, the owners sure took their time to make this house feel like home. I just love the outdoor pool and hot tub! If i...
    5 of 5 stars Reviewed 5 July 2016
    Loved, loved, loved this house! Everything about my stay was fantastic. The house is beautifully furnished and well maintained, from the well appointed kitchen to the pool. It was...
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    1 / 32
    5 of 5 stars (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    'Imagine Renting This Luxury Villa Overlooking The Beautiful Private Lake, In Orlando`s Most Prestigious Resort, Windsor Hills' This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa is in an... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 27 June 2015
    Thank you for viewing this listing however this property is presently under new ownership and is no longer accepting short term rentals.
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    1 / 28
    5 of 5 stars (55) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Washer
    • Private Outdoor...
    • DVD Player
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    WINNER OF TRIP ADVISOR's 'CERTIFICATE OF EXCELLENCE'. ALSO WINNER OF FLIPKEY's 'TOP VACATION RENTAL' Luxurious 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 few minutes from Disney and other... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 6 August 2016
    This really is the perfect vacation home. This was our second visit to Disney Haven and we will most definitely be back! The house is clean and comfortable and exactly like the...
    5 of 5 stars Reviewed 22 July 2016
    After a long search looking for the perfect place to stay we found Disney Heaven and were not disappointed, The photo's of the property were a true reflection of the house...
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    1 / 31
    4.5 of 5 stars (5) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Located in Windsor Hills, the Vacation Resort Community only 5 minutes away from Disney World, this house provides your family and friends with all of the outstanding pleasures of a 5 star hotel, while guaranteeing you the privacy, cleanliness and convenience of your very own home. This luxurious... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 9 April 2014
    Better than the photos. Clean, great amenities at Windsor Hills. Perfect for multigenerational families. Pre stay information very helpful
    5 of 5 stars Reviewed 29 March 2012
    I really enjoyed my stay here. It was very clean and had updated furnishings. The only issue I had was the jacuzzi not getting warm...the area was great and close to everything...
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    1 / 28
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Riviera Royale has everything that you and your family could possibly need for the most magical vacation to Disney and the attractions of Kissimmee and Orlando, Florida. Situated less than 2 miles from Disney's doorstep, located in the fabulous Windsor Hills resort community, this vacation home... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 16
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Washer
    • Patio
    • Satellite TV
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    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Make your Disney Dreams a reality when you stay in this beautifully decorated, three bedroom town home located in the gated community of Windsor Hills Resort. We have thought of everything to make your stay a wonderful experience. With the convenience of home so close to the magic! Located just off... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 16 April 2012
    We absolutly loved our stay at Close2theMagic. The Location was great! It was so close to everything we never had far to drive. We especially loved the heated pool that helped...
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    1 / 18
    4.5 of 5 stars (21) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
    • ?
    About this property
    Superb Vacation Home on the popular Windsor Hills Resort, and just 5 minutes drive from Walt Disney World resort. The home, which is fully furnished in contemporary style, provides a spacious lounge/dining room with patio doors to a covered lanai, a fully fitted kitchen with breakfast bar and a... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 18 February 2016
    Great location close to many shops, restaurants, and stores. Very close to Disney theme parks. In a very nice gated community. Very safe for families especially those traveling...
    5 of 5 stars Reviewed 26 March 2015
    Exactly how it looks in the picture. We would definitely rent this property again. The heated pool was perfect after a day of walking many miles. Kathy from Advantage Vaction...
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    1 / 27
    5 of 5 stars (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Balcony
    • Washer
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    FLORIDA SUN AND FAMILY FUN AT SUNSHINE GETAWAY CONDO LOCATED AT 5 STAR WINDSOR HILLS RESORT! Family friendly 3bedroom/2bath condo with free wireless internet our condo named Sunshine Getaway is your next vacation retreat! On the third floor this condo is a quiet corner unit overlooking an... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 16 June 2015
    This condo was a great find! The owner was wonderful to work with and very accommodating when we needed to move our reservations up a few days at the last minute. The resort was...
    5 of 5 stars Reviewed 26 October 2014
    Travelled with our daughter and 5 year old grandson. Picked Windsor Hills as family used to own a house here and we knew what a good resort it was. The condo is very nicely...
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    1 / 18
    4 of 5 stars (3) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Washer
    • Porch
    • DVD Player
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    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Best luxury house in Windsor Hills Resort!! Our 6 bedroom 4 bathroom Disney Dream House. The largest most luxurious home in the 5 star gated resort of Windsor Hills! Just 2 miles from the gate of Walt Disney World! Our home features - South facing private pool and spa. Top notch electronic... View all property information
    Location Information
    Kissimmee, Central Florida
    4 of 5 stars Reviewed 16 April 2014
    We had a group of 11 including my parents who have limited mobility. Having a master bedroom with bath downstairs was so nice for them. I only wish there was a stand alone shower...
    4 of 5 stars Reviewed 2 November 2013
    Everything about this property is exactly what we expected. Two masters upstairs (opposite ends of the floor), three GREAT themed rooms, and another king bed down stairs with a...
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    1 / 19
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Guests love the homey comforts of our Cleveland vacation condo, located in the prestigious Windsor Hills resort community. This 4- Star condo is built with 2 bedrooms and 2 bathrooms across nearly 1100 square feet of vacation living space. Enjoy the views from your private balcony! Although the... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 12 March 2010
    I taveled with my husband and two boys 13 and 7 and stayed for a week. The place was spacious clean ans well kept the 2 bathrooms were a plus for getting ready and who can beat...
    5 of 5 stars Reviewed 3 March 2010
    We were very pleased with our accommadations and the friendly service that was provided by your office and the staff at the Windsor Hills Resort. The beautiful complex pool was...
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    1 / 31
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • Smoking allowed
    • ?
    About this property
    'Picture this…Renting this 5 Star Luxury Villa in one of Orlando’s most Prestigious Resort, Windsor Hills. Only 5 minutes from Disney World and with it's own Private Pool and Games Room You and Your family will have a Wonderful Holiday' This villa is situated in the exclusive resort of Windsor... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 32
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • ?
    About this property
    'Picture This...You Renting a 5-Star Villa in Orlando`s Most Prestigous Resort, Windsor Hills, Only 1.5 Miles from the Gates of Disney' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The... View all property information
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    Kissimmee, Central Florida
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    1 / 22
    4.5 of 5 stars (19) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Private Outdoor...
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    • Pet-friendly
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    • ?
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    About this property
    PREMIER 5 STAR COMMUNITY The Windsor Hills Resort is a gated community located within the heart of Orlando’s premier tourist attractions, Windsor Hills is a 5 star resort within 2 miles of Disney World. Some of the magnificent features of Windsor Hills includes a guarded and gated lakefront... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 7 June 2016
    We loved the house! It would be great to have enough cups and bowls for everyone to have a bowl of cereal in the morning tho. We bought styrofoam additions tho, and that solved...
    5 of 5 stars Reviewed 3 May 2016
    My family love everything about home and staff was very courteous and on point with everything! Would highly recommend the company!
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    1 / 24
    5 of 5 stars (5) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Internet Access
    • Patio
    • Hot Tub
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in beautiful Windsor Hills Resort, our Florida Vacation Home rental is only 2 miles from Disney!! Our home offer six bedrooms, four bathrooms and has been professionally furnished and decorated. Offering 3000 sq ft of living space, a Lanai overlooking the private pool and spa, a large... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 33
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Hot Tub
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    OK, so you do not need a 4 bedroom, perfect, here is an awesome freshly refurbished 3 bed 3 bath Town Home in Windsor Hills. Freshly refurbished 3 bed 3 bath town home with pool with a Micky and Minnie themed bedroom. Beautifully furnished in contemporary design this awesome 2-Story Town House... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 21 September 2014
    We completely enjoyed our stay here. The rental process was easy and professional. The owners care for their property and very much want to make sure that their guests have...
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    1 / 28
    4.5 of 5 stars (19) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Disney Clubhouse is a spacious Disney vacation townhome with spa-pool which can accommodate up to eight guests and is perfectly situated in the fabulous Windsor Hills resort community, less than three miles from Disney and the attractions of Kissimmee and Orlando, Florida! Located in beautiful... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 10 August 2011
    We really enjoyed our stay. The pool, the rooms... It's a little hard to find, since we didn't know it was behind a gate. Also, there was 1 disney themed room. With three kids...
    5 of 5 stars Reviewed 2 June 2011
    Everything about our vacation was amazing, including the "clubhouse". The kids loved the themed room and it was nice having a small pool to relax after a long day at the parks...
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Windsor Hills Resort is a secure guard gated community located 1.5 miles to Disney World within the heart of Orlando’s premier tourist attractions! Luxury, privacy and five star vacation resort amenities bring this holiday condo rental to an executive level beyond its class! The resort features... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 21
    4.5 of 5 stars (21) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    Disney's Castle is a spacious Disney vacation townhome with spa-pool which can accommodate up to eight guests and is perfectly situated in the fabulous Windsor Hills resort community, less than three miles from Disney and the attractions of Kissimmee and Orlando, Florida! Located in beautiful... View all property information
    Location Information
    Kissimmee, Central Florida
    4 of 5 stars Reviewed 23 July 2015
    Check in is easy and great location to Magic Kingdom. The pool at the backyard is great for small children. Owner Mary responds to all my concern promptly.
    4 of 5 stars Reviewed 8 February 2012
    This was our first time renting a vacation property and all and all it was wonderful! House was the perfect size for the 3 adults and 2 children traveling in our party. It was so...
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    1 / 49
    4.5 of 5 stars (31) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to the "Magic Palace", a stunning and luxurious Orlando vacation Palace. Located in beautiful Windsor Hills, a gated community just 1.5 minutes from the gates of Walt Disney World. This 5-star resort features a huge lagoon-style pool complete with water slide and hot tub, children's... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 9 November 2012
    My extended Family stayed at this home during a recent family reunion in Florida. I was the one that booked the home and dealt with the owner, Rita. She was fantastic to work with...
    5 of 5 stars Reviewed 14 March 2012
    We had 11 people staying in this home. We never felt crowded and hated to have to leave!
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    1 / 23
    4.5 of 5 stars (40) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Magical Dreams is a spacious Disney vacation townhome with spa-pool which can accommodate up to eight guests and is perfectly situated in the fabulous Windsor Hills resort community, less than three miles from Disney and the attractions of Kissimmee and Orlando, Florida! Located in beautiful... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 19 September 2012
    i laic the house and may children loved it to match and if i plan to come again it will be may plaice again
    4 of 5 stars Reviewed 26 March 2012
    Great stay to be with a family in Orlando. A lot of facilities, big spaaces, all amenities I expected to have. Great option.
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    1 / 14
    2 of 5 stars (1) Poor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    About this property
    Harmony House is a luxury villa located in the prestigious Remington Golf Community and near Walt Disney World in Kissimmee, Florida. This upgraded executive Villa with extended Pool & Spa, has 4 bedrooms and 3.5 bathrooms and sleeps up to 8 guests in luxury. Remington golf course has won a Disney... View all property information
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    Kissimmee, Central Florida
    1 / 25
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    "Picture this…Renting this 5 Star Luxury Villa in Orlando’s most prestigious resort, Windsor Hills. Only 5 minutes from Disney World and with it's own Private Pool and Games Room, you and your family will have a wonderful holiday" This villa is situated in the exclusive resort of Windsor Hills.... View all property information
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    Kissimmee, Central Florida
    1 / 4
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Windsor Hills Resort is known for beautiful vacation properties. The 5- Star Trafford condo is no exception. An open floor plan with over 1,400 square feet greets families and friends for a memorable vacation in Kissimmee. Its third floor location is easy to get to with the help of an elevator.... View all property information
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    Kissimmee, Central Florida
    5 of 5 stars Reviewed 2 March 2010
    all points was great, a beautifull flat or villa, a great swimming pool a strong sucurity
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    1 / 20
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Harmony Haven is a vacation home that has 4 bedrooms, 4 bathrooms, games room, fully screened in swimming pool, spa, and lanai. This fully air-conditioned vacation home is located less than 5 miles from Disney in Windsor Hills, a resort-style community. With its impressive entrance and manned... View all property information
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    Kissimmee, Central Florida
    1 / 36
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Professionally decorated, highly desirable Windsor Hills 5 Bedroom 5 Bath Pool Home, 5 minutes to Disney This 5 bedroom, 5 bath home has a west facing pool/spa and has open views from the back of the house and is waiting for you. This home has granite counters and stainless steel appliances in the... View all property information
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    Kissimmee, Central Florida
    1 / 27
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    'Picture this you and your family living in this beautiful villa with it's own private pool on the popular Windsor Hills Resort. While you are only 1.5 miles from the famous Disney World' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all... View all property information
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    Kissimmee, Central Florida
    1 / 25
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    'Picture This... You and Your Family Living in this Beautiful Villa with it's Own Private Pool on the Popular Windsor Hills Resort' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa... View all property information
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    Kissimmee, Central Florida
    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    The Heathrow is a beautiful 5-Star vacation rental home located in the Windsor Hills Resort of Kissimmee, Florida. Guests will enjoy the great location, amenities, fine furnishings, and brilliant décor. Its location is in close proximity to the popular Disney parks, Universal Studios, and Sea World... View all property information
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    Kissimmee, Central Florida
    1 / 29
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    "Picture this...Renting this 5 Star Villa Holiday Home in Orlando Florida. With it's own Private Pool, Spa and Games Room. You and your family can have a Wonderful Holiday while Staying Here" This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and... View all property information
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    Kissimmee, Central Florida
    1 / 17
    5 of 5 stars (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Our villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. <BR><BR>There are four bedrooms complete with full baths: two king-sized master suites, a queen and a bedroom with twin beds. The chair in the nook makes into a twin, too. Each bathroom has a hair... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 20 January 2016
    WOW is all we have to say about our stay at Disney World Amarillo Villa (8 nights) and Townhouse (4 nights) Our experience was a 10/10 from the time we started planning until we...
    5 of 5 stars Reviewed 12 January 2016
    We stayed 2 weeks in Katie's 3 bedroom & 3 bath villa from the end of April to mid May and couldn't have been more happy with it. The location, the villa and its facilities, and...
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    1 / 30
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    'Imagine Renting This Stunning Villa with it's own Private Pool and Games Room In Orlando`s Most Prestigious Resort, Windsor Hills' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa... View all property information
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    Kissimmee, Central Florida
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Birmingham, professionally managed by Magical Memories, is a beautiful 5-Star luxury condo that lies within the secured gates of the Windsor Hills Resort just west of Walt Disney World. Guests are spoiled with 1400 square feet of vacation living space. The fourth floor location allows for... View all property information
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    Kissimmee, Central Florida
    1 / 10
    3 Bedrooms, Sleeps 6 | Quick View
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    About this property
    Floor Plan (Sonoma) 1st floor condo: 1,247 sq. feet Newly decorated and upgraded 1st floor 3 bedroom, 2 bath condo located in the beautiful Windsor Hills gated community just 2.5 miles from Disney property. The home comes with a 42" flat screen TV in the living room with a Playstation 3 game... View all property information
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    Kissimmee, Central Florida
    1 / 3
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The 5- Star rated Sunderland vacation condo at Windsor Hills Resort features over 1200 square feet of vacation living space. An elevator is available to take you up to the fourth floor to enjoy your accommodations. Inside, you’ll find cool tile flooring throughout the main living areas and... View all property information
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    Kissimmee, Central Florida
    1 / 26
    4.5 of 5 stars (13) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Day Dreamer is a spacious Disney vacation townhome with spa-pool which can accommodate up to eight guests and is perfectly situated in the fabulous Windsor Hills resort community, less than three miles from Disney and the attractions of Kissimmee and Orlando, Florida! Located in beautiful Windsor... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 14 November 2011
    En mi caso viajamos 6 personas con una bebe de un año y no tuvimos ningun problema, la casa tiene todo lo suficiente para poder pasar unas excelentes vacaciones.. Los dormitorios...
    4 of 5 stars Reviewed 1 August 2010
    Windsor hills is phenomenal. It has a great facility with everything you can imagine. And when you combine that with great accommodations like the Day Dreamer, there is nothing...
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    1 / 36
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Beautiful 2 Bed 2 Bath Condo with Two King beds, 5 minutes to Disney This awesome professionally decorated 2 bed, 2 bath condo not only has a fantastic location, it also comes complete with gorgeous furnishings; including upscale furnishing and bedding. While you are here, you can rest easy in your... View all property information
    Location Information
    Kissimmee, Central Florida
    4 of 5 stars Reviewed 2 March 2015
    We enjoyed our stay at Windsor Hills so much that we would definitely return in the future! From our arrival at the gate to our departure we can say we had an enjoyable, relaxing...
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    1 / 14
    5 of 5 stars (71) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Travelling to Orlando and Walt Disney World? Why stay in cramped, expensive hotel rooms when you can rent this luxurious 5 bed villa which is only 5 minutes from the entrance to Walt Disney World. Be our guests and enjoy all the incredible facilities of the renowned 5 star Windsor Hills Resort;... View all property information
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    Kissimmee, Central Florida
    4 of 5 stars Reviewed 18 February 2016
    We really enjoyed our stay here. It was clean and comfortable. At the end of our 3 days, I didn't want to leave. The only reasons I did not give it a 5 was because the pool...
    5 of 5 stars Reviewed 27 November 2015
    This villa exceeded my expectations! This villa easily accommodated our party of 10! I really loved that each bedroom had it's own private bathroom, this made getting ready each...
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    1 / 22
    5 of 5 stars (27) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Princess Ballroom is a spacious Disney vacation townhome with spa-pool which can accommodate up to eight guests and is perfectly situated in the fabulous Windsor Hills resort community, less than three miles from Disney and the attractions of Kissimmee and Orlando, Florida! Located in beautiful... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 15 October 2012
    We stayed here for over a week in June 2012. It was myself and my 2 daughters. There were 3 bedrooms that were relatively large. Nice touch of a cake when we arrived. My...
    5 of 5 stars Reviewed 19 September 2012
    I've been in a 3 bedroom Princess Ballroom during 5 wonderful days when my 4 yo daughter enjoyed her Ballroom as a real Disney Princess. The House has everythink to make your stay...
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    1 / 36
    5 of 5 stars (4) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    Stunning 6 Bedroom 4 Bath Home with Private, South Facing Private Pool in Highly Sought after Windsor Hills Resort Beautiful six bedroom, four bathroom home in highly sought after Windsor Hills Resort with private South facing pool and game room. Only two miles to Disney World! Professionally... View all property information
    Location Information
    Kissimmee, Central Florida
    4 of 5 stars Reviewed 25 June 2015
    We enjoyed our stay in this 6 bed room home The house is great and clean and it has all your needs Some drawback was related to the swimming was not clean when we arrived and...
    5 of 5 stars Reviewed 27 March 2014
    We travelled to Orlando with our 2 children and our live in caregiver and we could not have had a better experience. This home is ideally located to Disney World (10mins to...
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    1 / 9
    3 Bedrooms, Sleeps 6 | Quick View
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    Welcome to this beautiful Saddleback Model ( 1600 sqft.) 3 bedroom 3 bath townhome (2 story) East facing pool This tranquil but pristine three-bedroom, three-bath vacation townhome provides you with everything you will need for the perfect holiday escape. The first floor has an open floor plan with... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 10
    3 Bedrooms, Sleeps 6 | Quick View
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    Floor Plan (Sonoma) 1,247 sq. ft. 4th Floor Condo We invite you to enjoy our condo on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful 4th floor condo in the Windsor Hills Resort.... View all property information
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    Kissimmee, Central Florida
    1 / 36
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    4 Bed 4 Bath Hey Kids, how would you like to stay in this home on your vacation? Closest large resort to Disney is where you will find this 4 bedroom 4 bath home with a private pool. Windsor Hills offers the convenience of being close to the attractions, shopping, golf and great restaurants. This... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed 28 April 2016
    Just stayed here with my daughter, son-in-law and grandchildren. Enjoyed the location, close to Disney. Appreciated that this is a gated community. Was very worthwhile to have the...
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