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Holiday Rentals in Kissimmee

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    Travellers to Kissimmee are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    75 Matching Rentals in KissimmeeView all 5,489 rentals
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    Stunning Villa at the Windsor Hills Resort, 2 miles to Disney1 / 30
    (53)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Windsor Hills,own cinema room, Xbox one, free WiFi1 / 54
    (9)Excellent
    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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    Luxury 6 Bedroom Home with Pool at Windsor Hills Resort1 / 132
    (4)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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 - 2689 Manesty Lane ~ RA43801 / 12
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    This vacation rent home is spacious enough for large groups and allows for a comfortable and very enjoyable stay even when taking a break from all of your vacation outings...
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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. Absolutely perfect for large family groups, this property features all the comforts of home and more! Windsor Hills is a gorgeous gated community just 1.5 miles from...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    2sistersdisneycondo at Windsor Hills, near Disney1 / 76
    (82)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Grill
    • Hot Tub
    • Patio
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Loved our stay with the grandchildren making memories at the theme parks without hotel hassle. Loved the 2sisterscondo accommodations for time away from crowds to regroup but...
    Reviewed 16 June 2017
    When we arrived at our condo, we were simply blown away at how beautiful it was! We had everything we needed right in the condo- in suite laundry, huge comfy beds, a HUGE...
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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 Retreat Villa1 / 20
    (3)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 14 December 2016
    My family and I have been going to Florida annually for the last 5 years, and we have stayed in houses on Windsor Hills a number of times, but from now on this is the only house...
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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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Great location, very clean, plenty of room, well furnished, neat pool, very safe place to stay, trash pick up daily (perfect), great community pool and fitness center. A...
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    About this property
    Great location, 3 bed 3 bath town home with private pool in Windsor Hills. Walk to club house and main pool This 2-Story Town House has its own private pool with a covered and screened Lanai. Come home from an exciting day Disney World or other area attractions and hang out by the pool to relax and...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windsor Hills Family Condo 2 miles 2 Disney!1 / 27
    (18)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
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    We had a wonderful time in this condo. The check-in / check-out procedures were so easy. The complex felt secure and amenities were great for our family. The unit was stocked...
    Reviewed 16 May 2017
    all the major tourist attractions are nearby. Very clean and upgraded condo. We will definitely consider this condo on future Florida vacations.
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    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...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Children's Pool
    • Hot Tub
    • Satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Kissimmee, Central Florida FL 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Disney Windsor Hills 6BR/4BA Villa1 / 27
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • 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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Close2theMagic 3br/3ba Townhouse Windsor Hills1 / 19
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Aug -Sept Special.~ Windsor Hills 3BD/3BA w/FREE Pool Ht  Welcome Pk1 / 45
    (23)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 4 June 2017
    The vacation home was amazing! It was clean, organized, and basically a wonderful temporary home from home. The gated 24/7 manned security was also a nice feature. The owner was...
    Reviewed 6 April 2017
    Stayed here with my 2 daughters and my parents for out Spring Break vacation, it was everything promised in the ad! Was super clean and organized, had everything we could want...
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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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 9 Bathrooms, Sleeps 8
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    2627 Windsor Hills1 / 32
    (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
    • 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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 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
    • DVD Player
    • Parking
    • 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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    Kissimmee, Central Florida 34744
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lovely Harmony Haven has a Gameroom, WiFi, and Air Conditioning1 / 20
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windsor Hills 3 Bedroom Condo located just 2 minutes from Disney1 / 11
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2017
    We rent a condo for a month every year so we have had a lot of experience,both good and bad. This was pretty good. We have stayed at Windsor Palms before so we knew the general...
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    About this property
    BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET in the Condo, FLAT SCREEN HDTV's ALL ROOMS, DVD PLAYERS, Private Washer/Dryer BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury Condo in Orlando near Disney- Windsor Hills1 / 31
    (22)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Internet Access
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    • 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
    Why 'inquire', when you can use 'Book Now' at our listing to confirm your reservation online immediately? 1) Our calendar here is always 'up-to-date'. 2) Our best rates are available only online. When you 'inquire', our staff visits this listing and then uses the pricing available online to send...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Affordable Luxury for Your Family Next to Disney1 / 11
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    This condo was everything we needed and could ask for, each child had there own bed ages 3, 9, 15. We had a beautiful King to stretch out in after the day was through. We would...
    Reviewed 9 January 2017
    We stayed here for 7 nights for our trip to Disney and Universal Studios. The location was perfect - 20 minutes to Universal Studios and 10 minutes to Disney. The condo 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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Villa 2617 Daulby St Windsor Hills1 / 32
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Kissimmee, Central Florida 34747
    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
    (10)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The kids absolutely loved the house & pool area. I enjoyed the kitchen and many dishes and utensils that were available for use. Very close to resort pool & movie theatre...
    Reviewed 2 June 2017
    I was in awe with this house ever since I saw a picture of it – not only was it a perfect family-sized house, but it's distance to amusement parks amazed me. Truth be told, I am...
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    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Windsor Hills 6 Bedroom Luxury Villa - near Disney1 / 34
    (7)Excellent
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • DVD Player
    • Wi-Fi
    • 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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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Professionally decorated, highly desirable Windsor Hills 5 Bedroom 5 Bath Pool Home, 5 minutes to Disney A Picture is Worth a Thousand Words, But a Virtual Walkthrough Speaks for Itself! Click Here for a 3D Virtual Tour of This Home! This 5 bedroom, 5 bath home has a west facing pool/spa and has...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Luxury 2 miles from Disney w/Princess Rm, Pool/Spa1 / 36
    (5)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Porch
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    7669 Windsor Hills1 / 33
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windsor Hills WH0091 / 20
    (20)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Location was great. Agency staff were very friendly, House was furnach and fitted to a rental quality.
    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...
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    About this property
    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 resort community include: a...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    WIndsor Hills WH0111 / 18
    (22)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
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    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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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 it...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    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 décor. Its location is in close proximity to the popular Disney parks, Universal Studios, and Sea World...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bathrooms, Sleeps 10
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    7664 Windsor Hills1 / 37
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    • Satellite TV
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    • 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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cleveland at Windsor Hills1 / 6
    (2)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
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    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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beautifully decorated new 3 bedroom 2 bath condo in sought after Windsor Hills resort community. Near clubhouse with resort style pool, sundry shop, fitness center, water slide, billards, gameroom, and movie theater. Just 1.5 miles to Walt Disney World! Resort Amenities: Huge Lagoon-Style...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    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. 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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE,  WINDSOR HILLS  3B/ 3B TOWN HOME1 / 29
    (60)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Family of 5 (two late Teens and one early 20's), this was our second time to stay in this property, each occaison it was for 17 days.The Property is excellent, with 3 beds and 3...
    Reviewed 4 weeks ago
    This was our 2nd time staying at this house and it was as good as before. The owners cater for all aged families and have high chairs, portable cot etc available. Our...
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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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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    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 east facing pool and spa with a beautiful lake view.   Attention to every detail has...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Terrace
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    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 south-west facing pool and spa.  Attention to every detail has been put in as we...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    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 preparing a family feast...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
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    Pet friendly
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    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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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    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 to visit and enjoy...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    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 areas that will make...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy the warm sunshine of Florida, the magic of the Orlando theme parks and the amenities of this wonderful resort at our family-friendly home in Kissimmee. This gorgeous 3-bedroom, 3-bath townhouse has a private, screened-in patio with a splash pool and backs up to a large open space where kids...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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