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Kissimmee Villas

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    Travellers to Kissimmee are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    21 Matching Rentals in KissimmeeView all 4,247 rentals
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    April 6-11& 23-30Special.~Windsor Hills 3BD/3BA w/FREE Pool Ht & Welcome Package1 / 24
    (28)Excellent
    3 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    Luxury 2 miles from Disney w/Princess Rm, Pool/Spa1 / 18
    (8)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Executive Villa, Pool, Hot tub, WiFi, Games Room1 / 51
    (13)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Windsor Hills End Unit Townhouse 2 Miles 2 Disney's World Drive1 / 47
    (53)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Patio
    • Cable/satellite TV
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 October 2014
    This townhouse in Windsor Hills resort is a great place to stay for a family wanting to visit the Disney and Universal theme parks and also to explore the Orlando area.This...
    Reviewed 9 May 2014
    I rented the house for the second time, so enjoyed the first experience, I decided to repeat and I can go back to rent again. I was not disappointed, the house is very well...
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    About this property
    Windsor Hill Resort is the closest resort of its kind to Walt Disney World. Only 2 miles from Disney's World Drive that takes you to all Disney Parks, this gated resort has luxury amenities which include a lagoon style swimming pool with water slide, billiards, tennis, basketball, putting greens,...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Close2theMagic 3br/3ba Townhouse Windsor Hills1 / 43
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    It was nice besides a bunch of tiny little ants or what ever they were all over kitchen counter, floors, and bathroom. The wood on downstairs bedroom walk way was loose...
    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...
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    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Affordable Luxury for Your Family Next to Disney1 / 17
    (18)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2018
    The apartment is as described and was perfect for the four of us. It was fitted out with everything we needed and very comfortable. The slow cooker was a particular bonus as it...
    Reviewed 30 December 2017
    We needed a place to stay near the Parks and our daughter who lives nearby. This location was perfect for what we needed. The lines to get into the gated community (which is...
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    About this property
    This property is only accepting bookings that begin by January 11. 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....
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury 6 Bedroom Home with Pool at Windsor Hills Resort1 / 50
    (5)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    The home was clean and accomadated my family very well. The clubhouse swimming pool was great for the kids. I just wished the pool at the house wasn't so deep.
    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...
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    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Windsor Hills 3 Bedroom Condo, Less Than 2 Miles to Disney1 / 82
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2014
    This condo has everything you could need in your home away from home. The kitchen was well stocked to prepare any type of meal. The rooms and bathrooms were nice and clean...
    Reviewed 18 September 2013
    We really enjoyed our stay at Windsor Hills. I only gave it a 4 star because we did have a little hiccup with the pool slide. Apparently you have to be 42 inches to get on it...
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    About this property
    Windsor Hills is the newest and greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort. Our 3 bed/2 bath (1 king, 1...
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    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mickeys Masterpiece in Windsor Hills1 / 61
    (13)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2019
    This house was truly amazing! Had a great week and was totally worth it. Would definitely book again.
    Reviewed 29 July 2017
    The house was stunning. Clean and well maintained. Had to have the air conditioner checked the first day we were there, and the office staff and the guy who did the service...
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    About this property
    Welcome to this elegant and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. The home boasts views for miles as there's no rear neighbors. You can even see the nightly fireworks at Disney World. Absolutely perfect for large family groups, this...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Luxury Condo in Orlando near Disney- Windsor Hills1 / 37
    (22)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2014
    Very nice condo very close to all of the Disney properties! Owner was concerned about our stay and was very friendly. This is the best deal for your dollar in and around Disney.
    Reviewed 10 June 2014
    This condo was perfect for our stay. It was exactly as pictured and VERY clean. Prem was great! He was very responsive and helpful. He even sent all of the pertinent information...
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    About this property
    If you like what you see below, please go ahead and using 'Book Now' button, make reservation online with confidence. Our 3 bed 2 bath 1250 sqft resort-style luxury condo at Windsor Hills Resort offers you 'home away from home' experience. We offer you the ability to relax and unwind in an...
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    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Penthouse 3 bed 2 bath Condo, Sleeps 8 and very Kid friendly 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 highly desirable resort of Windsor Hills. The community is...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Windsor Hills Retreat Villa1 / 20
    (4)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2018
    From the moment we arrived and crashed out, we were totally at home in this lovely villa and really enjoyed our two week stay.Windsor Hills is a lovely gated community so felt...
    Reviewed 4 January 2017
    Beautiful villa with lots to do. The pool & spa were gorgeous. Bedrooms were huge & lots of space for clothes etc. Games room was great. Was a huge villa for the 4 of us...
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    About this property
    2 miles to Disney - Luxury 6 bed, 4 bath - South facing private Palm Tree lined pool & spa with covered patio area. No expense spared, large LCD flat screen TVs in every room, premium & HD cable channels, Sony BluRay/DVD players, Nintendo Wii, Xbox 360, iHome alarm clocks and Bose sound system....
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    7669 Windsor Hills1 / 36
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2017
    We traveled to Kissimmee for a family member's wedding. We had relatives coming in from Seattle and Vancouver BC. Most of the family stayed at a 6 bedroom house nearby...
    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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    About this property
    Is a 4 bedroom too large for your party? Perfect, here is an awesome freshly refurbished 3 bed 3 bath Town Home in Windsor Hills! A Picture is Worth a Thousand Words, But a Virtual Walkthrough Speaks for Itself! Click Here for a 3D Virtual Tour of This Home! Freshly refurbished 3 bed 3 bath town...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7664 Windsor Hills1 / 36
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    Come enjoy this beautiful 2 Bed 2 Bath Condo featuring Two King Beds. Located in the ever popular resort community of Windsor Hills, you are only moments away from the entrance of Walt Disney World. Shopping, restaurants and other area attractions are so close, you will never run out of things to...
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    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bed Pool Home, game room in Windsor Hills Resort 3 Mi to Disney (WH011)1 / 17
    (22)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    2627 Windsor Hills1 / 36
    (2)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    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 featuring a private pool, stand alone hot tub and ALL new appliances! Orlando's Windsor Hills offers the convenience of being close to the...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE,  WINDSOR HILLS  3B/ 3B TOWN HOME1 / 30
    (63)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    We absolutely loved this town home, it was perfect for us. Very clean and spacious and with everything that you could possibly need. Very family friendly. We stayed 10 days and...
    Reviewed 23 October 2017
    We spent a week at this wonderful condo. The accommodations are very comfortable. Nice beds. Each bedroom has its own bath! Plenty of space and very close to Disney. The...
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    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...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2sistersdisneycondo at Windsor Hills, near Disney1 / 65
    (89)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Grill
    • Hot Tub
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2018
    We have recently stayed here for the third time (May 7th to 26th), and once again loved it.Leila is a wonderful host who keeps in constant contact, from the time you enquire...
    Reviewed 19 April 2018
    We stayed in this condo for 4 nights. The size was perfect for our family of 3. In the past, we have had to rent a unit with 3 bedrooms so that our college aged son could have...
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    About this property
    This inviting 2 bedrooms / 2 bathrooms condo with 1082 sqft is located at Windsor Hills, the 5-star gated & guarded resort only 2 miles away from Disney Maingate. This is a 1st floor unit, conveniently near building entrance and parking spaces, and at a short walking distance from the Clubhouse...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Windsor Hills Townhome, end unit/South facing pool1 / 27
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    This was a great place very neat and quiet the grounds are kept up nice and the townhouse was great it was nice to have a full kitchen and laundry available. The splash pool...
    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...
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    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...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Disney Windsor Hills 6BR/4BA Villa1 / 30
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This will be a brand new 5 star luxury 6 bedrooms 4 baths home located in the fabulous Windsor Hills Resort. It will be starting from January of year 2013. It is southern style home with numerous upgrades and it is furnished and decorated with very high standard. Our truly gorgeous vacation home...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Amarillo Villa Rental at Windsor Hills, Kissimmee - location, pool and spa1 / 25
    (15)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2019
    Just returned from a 12 night stay and highly recommend it.We chose Windsor Hills because we stayed here before . It is a very secure gated community with a newly developed...
    Reviewed 24 April 2018
    Although we've visited Florida and Disney World many times, we chose Amarillo Villa for our first experience of staying in a villa - we made a great choice!Our small family...
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    About this property
    FLA Holdings' Amarillo Villa accommodates 8 guests, and is equipped with everything needed to make your stay enjoyable. As a single-level bungalow, it is well suited for individuals with accessibility challenges. There are four bedrooms and four full baths: two king master suites, a queen suite...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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