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Holiday Homes in Kissimmee

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    Travellers to Kissimmee are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    51 Matching Rentals in KissimmeeView all 5 757 rentals
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    Executive Villa, Pool, Hot tub, WiFi, Games Room1 / 24
    (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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    Luxury 6 Bedroom Home with Pool at Windsor Hills Resort1 / 36
    (5)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Mickeys Masterpiece in Windsor Hills1 / 61
    (12)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 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...
    Reviewed 3 July 2017
    This house is about 5 minutes from the exit to Disney and about 20 minutes from Universal. The house was extremely clean and well taken care of. I would recommend this house...
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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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    34747, Kissimmee, Central Florida
    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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    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    6 Bed Pool Home, game room in Windsor Hills Resort 3 Mi to Disney (WH011)1 / 34
    (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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    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7669 Windsor Hills1 / 36
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 22 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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    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 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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    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Windsor Hills 3 Bedroom Condo, Less Than 2 Miles to Disney1 / 41
    (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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    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    34747, Kissimmee, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windsor Hills 6 Bedroom Luxury Villa - near Disney1 / 34
    (7)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2012
    We had 9 family members from ages 3 to 60 stay in this house for a week. Everyone loved it!! The booking process was very easy and we had excellent communication from the...
    Reviewed 28 February 2011
    We had great time for our family vacation at this villa. It was in a great location within the Windor Hills community on a quieter street with no backyard neighbors. The owners...
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    About this property
    This luxurious 6 bedroom, 4 bathroom villa is located on the 5 star gated resort of Windsor Hills which is only minutes away from the Disney theme parks. 2 themed rooms - Mickey Mouse and Toy Story. The villa has a private west facing pool, overlooking landscaped gardens and has recently been...
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    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2627 Windsor Hills1 / 36
    (2)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 with a private pool. Orlando's Windsor Hills offers the convenience of being close to the attractions, shopping, golf and great restaurants. This...
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    34747, Kissimmee, Central Florida
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dec 1-15 Special.~ Windsor Hills 3BD/3BA w/FREE Pool Ht & Welcome Package1 / 43
    (27)Excellent
    3 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    We were in town for a week long basketball tourney. This was exactly what we needed. Competitive pricing. Spacious enough. Clean. Well appointed. Secure. Close to Disney and...
    Reviewed 12 March 2018
    We stayed at Windsor Hills for 10 days during December. What an awesome time , the home was really a home away from home, as we were into our 3 week of our US holiday and were...
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    About this property
    Disney Dreams Vacation Home “is a spacious Orlando vacation town home in the heart of the exclusive Windsor Hills Resort community, less than 2 miles from Walt Disney in Orlando, Florida. Our newly furnished town home is ready to welcome you to your Florida vacation. This 3 bedroom home is...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 9 Bathrooms, Sleeps 8
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    Windsor Hills Townhome, end unit/South facing pool1 / 54
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    • Private Outdoor Pool (Unheated)
    • Washer
    • Porch
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2018
    This villa is soooo close to Disney - perfect - especially if you use the 'back entrance' down Sherbeth off the 192 and go past the Animal Kingdom. Bedrooms were beautifully...
    Reviewed 21 August 2018
    My family and I had a very good time . House was very clean and neat . I only have one suggestion. Maybe changing the comforter in the master bedroom upstairs. It was kind of...
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    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...
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    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Mi to Disney - 5BR/5BA- Wireless Hi Sp & Game Rm1 / 24
    (16)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2018
    Spent a wonderful time enjoying the property. Everything was clean and well-maintained. Comfortable and inviting interior with everything we needed. The patio and pool area were...
    Reviewed 13 October 2018
    Perfect place to stay when visiting the Orlando area. Plenty of room for your whole family without crowding. Loved the private pool! Kids will love the slide at the community...
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    About this property
    Truly the 'King' 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 Hour...
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    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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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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    • 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
    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...
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    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 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
    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cleveland at Windsor Hills1 / 22
    (2)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 2 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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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 decor. Its location is in close proximity to the popular Disney parks, Universal Studios, and Sea World...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 5 Bathrooms, Sleeps 10
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    34744, Kissimmee, Central Florida
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Trafford at Windsor Hills1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • DVD Player
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    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2010
    all points was great, a beautifull flat or villa, a great swimming pool a strong sucurity
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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....
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Washer
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    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxuriously appointed 3 bedroom, 2 bath top floor unit in the beautiful Windsor Hills resort that sleeps 6 comfortably. This elegantly decorated Kissimmee vacation condo is located in a gorgeous gated community just 5 minutes from the gates of the Magic Kingdom. This 1,247 sq ft condo has a...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Book your Orlando rental home now at this beautiful and professionally decorated 6 bedrooms and 4 bathrooms ''Grand'' 2 story 2812 sq. ft.home with west facing pool and spa. The home features a 50 inch flat screen TV in the living room. The dining room offers plenty of space...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Washer
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1st floor 3 bedroom, 2 bathroom condo. The home comes with a 42' flat screen TV in the living room with a Playstation 3 game system and flat screen TV's in each of the bedrooms (two 32' and one 24' with DVD). There is leather furniture in the living room along with a fully equipped kitchen and a...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amarillo Villa Rental at Windsor Hills, Kissimmee - location, pool and spa1 / 24
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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 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...
    Reviewed 20 February 2018
    We stayed at 7739 Comrow Street, which is located in the gated community of Windsor Hills Resort in Kissimmee, which is a quiet gated community. It is a four bedroom home with...
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    About this property
    FLA Holdings' Amarillo Villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. Being 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 and a...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>We invite you to enjoy our home 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 home with west facing pool and spa located in the Windsor Hills Resort....
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>This is the perfect home when you want plenty of space to host lively gatherings for family and friends, or if you just want a quiet, relaxing vacation.  The dramatic foyer sets the stage for this well planned layout.   This home boasts many comfortable conversational...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Sunderland at Windsor Hills1 / 27
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * PLEASE NOTE, THAT THERE WILL BE ADDITIONAL CHARGES DUE UPON ARRIVAL. 1.) AN ADDITIONAL CHARGE OF THE 6% COUNTY OCCUPANCY TAX TO THE SUBTOTAL. WE ARE COLLECTING ON BEHALF OF OSCEOLA COUNTY, FLORIDA. AIRBNB DOES NOT COLLECT THE FULL TAX DUE, ONLY FLORIDA STATE TAX. 2.) A $35 DAMAGE WAIVER AND...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>We invite you to enjoy our home 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 home with south-west facing pool and spa.  Attention to every detail has...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Terrace
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Attention to every detail has been put in as we...
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    Location Information
    34747, Kissimmee, Central Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We invite you to enjoy your next vacation at our beautifully decorated 3 bedroom/3 bath Townhome 1,416 sq. ft. with a fun east facing splash pool. Sleeping accommodation features an elegant master suite with king size bed; second bedroom with a queen size; and a third bedroom with 2 twins enabling...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Washer
    • Balcony
    • Patio
    • Private Outdoor Pool (Unheated)
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>5 bedroom, 5 bath property. After an energetic day exploring the sights and sounds of this magical playground you can return home to your own pool and spa area, or relax in front of the 50 inch TV. This property also benefits from a fully equipped kitchen that is ideal for...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Washer
    • Parking
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>We invite you to enjoy our luxurious Villa on your next trip to Orlando. Absolutely stunning, this professionally decorated and furnished property features all the comforts of home and more! This 6 bedroom, 4 bathroom 2,812 sq. feet unit sleeps 13. With 2 King Master...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>1 story home with pool & spa (South-West facing pool) We invite you to enjoy our Orlando rental home on your next trip to Florida, absolutely perfect for families featuring all the comforts of home and more! This home features 4 bedrooms and 4 bathrooms (everyone can get...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Welcome to Windsor Hills Resort and this luxurious 6 bedroom, 4 bathroom rental home (2812 sq. ft.) located near the theme parks in Orlando, Florida. This rental home has attained the prestigious 'Grand' status for having an upgraded professional furniture package. This...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Enjoy an amazing vacation in Florida at this lovely home in Kissimmee. With five bedrooms and five baths, this property can accommodate up to ten people in comfort, and is perfect for large groups of friends or family. There is a private patio where you can relax in the...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Balcony
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>This 2,500 square foot 5B/5B Seville home sleeps 11 and is south facing for year round, all day Florida sun. The fully air conditioned ''dream come true'' home has luxurious tropical furnishings and is professionally decorated throughout. Your every need has been anticipated....
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Terrace
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Book your vacation now at this beautiful Orlando rental home with pool and spa located in Windsor Hills Resort. Absolutely perfect for family groups, this property features all the comforts of home and more! This 6-bedroom, 4-bathroom, 2812 sq. feet vacation home sleeps 12....
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Windsor Hills - 2653 Dinville Street1 / 15
    (1)Average
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2014
    We were allocated this property after booking through Virgin Holidays. This was our 10th visit in a row to a Orlando and we have always stayed in villa accommodation. What we...
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    div class='rtejustify'>We invite you to enjoy our home 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 home with south facing pool and spa. Attention to every detail has been...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>This very modern 6 bedroom 4 bathroom home has been professionally furnished and decorated including beautiful relaxing colors through-out the home with custom window treatments. No expense has been spared with this home which comes with every little item to make your...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Washer
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>We invite you to enjoy our home 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 2 story home with pool and spa. Attention to every detail has been put...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We invite you to enjoy our home 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 home with pool and spa located in the Windsor Hills Resort. Attention to every detail has been...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Villa La Dolce Vita is new 4 bedroom/4 bathroom Luxury Home that sleeps up to 10 people. Our villa is located in the new five star ***** Windsor Hills Reserve Gated Community, the newest, most luxurious and closest private home resort community to Walt Disney World. We...
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    Location Information
    34747, Kissimmee, Central Florida
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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