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Kissimmee Vacation Rentals

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    Travelers to Kissimmee are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Beautiful 6 bedroom Home1 / 36
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 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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    • Patio
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Our party of 13 people had PLENTY of room in this rental. When relaxing in the home, some of us where in the theater room enjoying one movie, others were in the family room...
    Reviewed May 13, 2017
    Fantastic home for large family vacations. Pool was wonderful for mid day breaks from Disney. Within 5 mins from Disney and easy access to main roads. Nice playground right...
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    About this property
    Our Villa in Windsor Hills is a BEAUTIFUL custom designed home. Windsor Hills is a secure gated community that has all the amenities of a 5 star hotel or resort, but with the comfort, convenience, and privacy of staying in a high end home. Facilities Air Conditioning Flat Screen TV's TV's and DVD...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Seasons Delight, Beautiful 5 Bedroom Villa in Kissimmee1 / 91
    (3)Excellent
    Downtown Kissimmee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
    • Parking
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We truly enjoyed our stay. The villa is beautifully decorated and clean with many amenities. The pool and spa were well-heated and the location was most convenient that is...
    Reviewed June 21, 2016
    This was a beautiful home, that was fully equipped for my families needs (12 in family). There was always plenty of hot water and the kitchen was fully stocked with dishes we...
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    About this property
    Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and minutes away from all the best...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    AMAZING HOUSE IN DISNEY1 / 47
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • DVD Player
    • Private Indoor Pool
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 24, 2016
    Our aim was to hit the amusement parks and have a nice play to relax after we returned and this was all that and more. The house itself is VERY clean, spacious, and the indoor...
    Reviewed January 1, 2016
    Our family rented this Kissimmee, Florida home over the Christmas holiday in 2015. The property is a gorgeous 5 bedroom, 5 bathroom home located in a gated resort. The house is...
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    About this property
    Property Type: 5 Bedrooms, 5 Baths House with Private Pool and Game Room. Floor Area: 3000 sq. ft.Location:Paradise Palms Resort, Disney Area This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney!! and within a couple miles to...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Prestige 4: Ultimate Luxury Windsor at Westside, South Facing Pool/Spa, GameRm1 / 29
    (2)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    This home is immaculate and has the best amenities! We had everything we needed to cook breakfast everyday, and the kids loved the clubhouse pool. We got the pool heating which...
    Reviewed July 4, 2016
    I rented this vacation home with my extended family and it was everyone's first rental home experience (we usually stay in hotels) and needless to say, we were very nervous...
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    About this property
    This 4,000 sq. ft. home is in the new Windsor at Westside gated community (sister community to Windsor Hills) and just minutes from Disney. 8 bedrooms and 6 bathrooms, with 4 en-suites. Pool area with heated, SOUTH-FACING pool, IN-GROUND Jacuzzi. Game room with seating, pool table and foosball...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Internet Access
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’ll feel right at home the moment you arrive at this fantastic Kissimmee vacation rental house, complete with luxury accommodations and a prime location mere minutes from the gates of Disney World! Boasting 7 bedrooms, 6 bathrooms, and enough sleeping arrangements for 16 guests throughout 4,600...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.1 / 24
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 2017
    We are just back from our trip and just want to say how much we enjoyed staying at Doral Woods. The villa was perfect for all our needs and we all loved the place. It was...
    Reviewed April 30, 2017
    I am not typically one to write reviews, however this Villa was fantastic. The villa was extremely clean and well maintained, exactly as described by the owner, Andy. All the...
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    About this property
    Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully...
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    Kissimmee, Central Florida 34758
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Magical Pool Villa - 4 Miles to Disney!1 / 39
    (11)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2017
    5 stars does not begin to do this place justice. You just need to book it and stay there. It is the perfect destination for families, you won't need to visit the theme parks!We...
    Reviewed April 29, 2017
    The home was more then we expected! Absolutely beautiful! My grandchildren literally starting crying because of their excitement! Thank you so much Michael! We made many...
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    About this property
    Our Magical Clubhouse is located 4 miles from Disney, Florida in Rolling Hills Estates, which is one of the closest communities to Disney. This villa is ideally situated close to Walt Disney World, Universal Studios, Sea World, and all Central Florida attractions. <BR><BR>The villa has 7...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 15
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This outstanding custom built home has been a private residence within the Reunion Resort until this year. No expense has been spared in the design, decor and furnishings to complete this dream residence whilst still retaining that 'homely' feeling throughout it's 6 bedroom 5 bathroom floor plan....
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    8 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Executive vacation home near Disney located in Emerald Island Resort is tastefully decorated throughout to make you feel at home. Accent painting, colorful curtains and nice furnishings. The villa is located a short walk from the club house and is on a private conservation lot. 2 King master...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 20
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Central Heating
    • Washer
    • Hot Tub
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4,000 sq. ft. home is in the new Windsor at Westside gated community (sister community to Windsor Hills) and just minutes from Disney. 8 bedrooms and 6 bathrooms, with 4 en-suites. Pool area with stunning LAKEVIEW, heated SOUTH-FACING pool and Jacuzzi. Game room with seating, pool table and...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5-bedroom suite, 6 bathrooms. Accommodates up to 10 guests comfortably and has a fully equipped kitchen. This townhome is equipped with high-speed wireless internet all throughout the unit, free of charge. **PLEASE NOTE: Summerville Resort is a BRAND NEW community, some parts of the resort are...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Large 3-Bedroom Resort Villa Near Disney1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Sauna
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 17, 2016
    chris is an awesome person that will take care of your concerns immediately!totally satisfied with our stay at the resort.
    Reviewed August 27, 2015
    Above and beyond our expectations! My wife and I are very particular about where we stay. The rooms were immaculate, staff was very friendly and helpful, amenities were great...
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    About this property
    This spacious and luxurious condo is great for families and very close to Disney and is situated on a large resort property is plenty of great activities. There are a total of 5 beds in the villa. The master bedroom features a king size bed, a large jacuzzi, and a master bathroom. The second...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    BRIGHT AND LUXURIOUS LAKESIDE 7 BR/5.5 BA VILLA1 / 32
    (5)Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 2016
    My family and I have just returned from a wonderful three week stay, there were three couples ad we were spoilt for choice by the four master bedrooms available all of which...
    Reviewed October 4, 2016
    We are from Edinburgh, UK for family holiday. The beautiful villa had all that we needed and beyond we loved the spaciousness the pool and spa was amazing the bedrooms lovely...
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    About this property
    Close to Disney, 4 King MB, 1 Queen Br, 2 Twin Br, 2 Air Beds, Sleeps up to 16 Welcome to Clyde's Cove! This lovely villa is a bright and spacious vacation home with 3000 sq/ft, 7 BR including 4 Master Suites. All Master Suites have private full bathrooms. The villa is only 10 minutes from Walt...
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    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Best Lakeside Villa at Paradise Palms in Kissimmee1 / 17
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My vacation rental was wonderful (looked just like the pictures). It was everything that I expected.
    Reviewed April 25, 2017
    This a great place to stay especially if you are visiting the theme parks in Orlando. Our kids loved having the pool outside our sliding door, but they really loved the short...
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    About this property
    Built as a Tropical Oasis and refuge away from the hustle and bustle of the nearby attractions, Paradise Palms Resort allows residents to enjoy some of the Very Best Entertainment in the world, while living in a Relaxing, Full-Service Resort environment that caters to your every need. Located in...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Dolphin Villa - Doral Woods, 5* rated with Wifi & Games1 / 56
    (28)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    This is our third time at the Dolphin Villa, this time for four weeks.Why do we return?Easy - excellent house, beautiful large and secluded garden, great swimming pool and...
    Reviewed April 2, 2017
    We stayed at Dolphin Villa for a week in March. We found the arrival help from Steve simply first class. He couldn't of been more helpful. His knowledge of the area and its...
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    About this property
    Over 10 Years listed with Holiday Lettings. 5 STAR Trip Advisor Reviews, please read them. They are very helpful! Perfect Location and Discounts for bookings over 2 weeks and FREE food arrival pack as standard to all our guests! Fully Air Conditioned + Paddle fans in all bedrooms, lounge & Lanai,...
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    Kissimmee, Central Florida 34758
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mickeys Masterpiece in Windsor Hills1 / 61
    (10)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • DVD Player
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    Nine of us (3 generations) had a great stay at Mickeys Masterpiece. It is conveniently close to all the resorts. We had plenty of space for 6 adults and three grandchildren. The...
    Reviewed May 30, 2016
    I traveled with my family and we had a great time. The house is really spacious and comfortable. One of the best things about the property is its location: we could easily reach...
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    About this property
    Welcome to this elegant and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. The home boasts views for miles as there's no rear neighbors. You can even see the nightly fireworks at Disney World. Absolutely perfect for large family groups, this...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Indian Creek this villa is situated in one of the closest residential communities to the Disney Theme Parks area, and less than a 30 minute drive from the Orlando Premium Outlets and Orlando International Airport this beautifully furnished five bedroom four bathroom pool home is perfect...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    A hideaway dream - an amazing spacious family home1 / 45
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    I think you guys did not indicate that the televisions in the main bedroom, and living room televisions have been updated. They are flat screen tv in the room. I cannot brag...
    Reviewed May 16, 2017
    A lovely spacious villa in a quiet neighbourhood but very close to many restaurants and amenities.The south facing garden was nicely warm to come back to after a full say out.
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    About this property
    A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional charge. This large, 4...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fantastic Five Bed1 / 18
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 20, 2016
    Had a fantastic holiday with my family... crammed so much in with only a weeks stay at this lovely villa which had everything you could need. Had an issue with one of the door...
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    About this property
    This beautiful 5 bed home is over 2 levels. The sparkling pool overlooks a lake with conservation beyond and is an idyllic setting for your Kissimmee stay. The bottom level has wooden flooring. Here you can relax on the bold striped sofa and watch the flat screen TV. There is also a separate...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Mufasa's Pride - Military / Police / Fire Special1 / 73
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    Very comfortable stay and very close to all the Disney parks. We looked forward to the comfort of this home after long days walking and walking and walking at Disney.
    Reviewed 3 days ago
    Mufasa's Pride was an excellent choice for our family trip to Disney. It is very close to all the parks and there are many restaurants and stores under 5 mikes from the house...
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    About this property
    Stretch out, relax, and enjoy our beautifully decorated five bedroom, four bath, vacation home in Disney's shadow. There are two master suites with king beds, private baths and access to the pool area. The third bedroom has a full bed with an adjoining full bath. The other two bedrooms each...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Waterfront
    • DVD Player
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 7-bed, 4.5-bath Kissimmee home can comfortably accommodate 14 guests throughout its well-equipped interior. Situated in an ideal lakefront setting, this property allows you to admire fantastic views while swimming in the private pool! Lush, green landscape surrounds this phenomenal Florida...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Luxurious house with pool and Spa on large lot1 / 28
    (4)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Satellite TV
    • Housekeeping Included
    • Hot Tub
    • Children's Pool
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    An absolutely fantastic villa kitted out as if it were your own home plus it has its own pool!! THe rooms are all a great size and the beds are seriously comfortable! The garage...
    Reviewed May 11, 2017
    Wonderful pool, hot tub and out door patio area. House was pristine, tastefully furnished and in a lovely quiet location. Also fantastic family communal pool with water slides...
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    About this property
    Our. Wonderful holiday home, On Windsor at Westside, a gated community. Our home has a large private South East facing pool and spa. The screened patio / lanai has been extended to give more room to sunbath. Or to lounge and relax. The largest on the community. Guests also have access to a gas...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    Downtown Kissimmee
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your Disney vacation Home! - Great swimming pool and spa - Accommodates up to 11 people - 5 bedrooms, 4 bathrooms - 1 Master Suite with King size bed; - 1 Master Suite with Queen size bed; - 2 bedrooms with full size bed. - 1 bedroom with bunk beds ( 1 full size and 1 twin bed) - New...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Sauna
    • Shared Indoor Pool
    • Grill
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious brand new house in leading rental home community in the Disney Parks area of Central Florida. With a stunning clubhouse and amazing water park, this luxury gated community offers easy access to theme parks, and is around a 6 minute drive to Walt Disney World. This spacious and comfortable,...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Hot Tub
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    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury on Vacation? Absolutely! Beautiful, spacious and professionally decorated home in one of the newest Disney area resort communities, Sonoma. This home is located less than 15 minutes from the entrance of Walt Disney World; less than 1 mile from endless shopping & restaurant options and right...
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    Kissimmee, Central Florida 34741
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    4 Bedroom Poolside Sunny Retreat with Fully Inclusive Price.1 / 49
    (17)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Private Yard
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    • Private Outdoor Pool (Heated)
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2017
    Stayed for a week, 7 of us , plenty of room and a great location for the main theme parks in a quiet residential area. Had an issue with a pipe burst but sorted same day with no...
    Reviewed January 8, 2017
    I spent 6 nights on this house and was one of the best. Mr. Steve is very kind and has responded to all my inquires. The house was very clean and better than the pictures in...
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    About this property
    Your beautiful vacation home is at Eagle Point, Kissimmee, one of the best possible locations for access to Orlando's famous theme parks, attractions and Golf Courses. When you stay in this executive pool home, you will get great views, great decor and a private location backing on to a...
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    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Villa Betty Boo at Hampton Lakes1 / 34
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 15, 2016
    Great place to stay! I was nervous since I had never rented a house before. Bernie (owner) was great at answering all of my questions with in 12 hours after emailing her. The...
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    About this property
    Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can sleep 8 - 9 people + infants...
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    Kissimmee, Central Florida 33897
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Only 4 miles to Disney, completely private pool and jacuzzi, sleeps 12! 5 stars!1 / 40
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2017
    We enjoyed our stay at the house by the mouse! Our daughter LOVED the pool and game room! Each room was decorated nicely and was very clean. It was extremely convenient only...
    Reviewed March 20, 2017
    Pur family absolutely enjoy this house so much the kids loved the themed rooms, the pool, and the game room. The neighborhood is very quiet and its just minutes from the parks...
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    About this property
    Be our guest and stay at the house by the mouse! We are within 4 miles of Walt Disney World!. Relax and Refresh in our completely private pool and hot tub that look out onto a pristine conservation area. We have 5 beds and 4 full baths. Your little princes and princesses will love our Mickey and...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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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 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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    *NEW - Afforable Townhome - 5 Miles from Disney*1 / 90
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
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    • Children's Pool
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    The location was perfect. We were only 15 minutes from Universal Studios. It was so convenient to be across the street from Sam's Club and down the street from Wal-Mart. The...
    Reviewed 1 week ago
    We just got back from a 4 day stay at this property. This was our second visit. We didn't go to any theme parks this stay. The complex is quiet, clean, and everyone is friendly...
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    About this property
    Cancel that hotel! Why stay in a cramped room when you can get a large, upscale condo. DELUXE FEATURES:...<BR> <BR>Villas at Seven Dwarfs Lane vacation townhome rental <BR>3 Bedrooms (Master bedroom is on the main floor and 2 other bedrooms are on the second floor), 2 Baths, Sleeps 6<BR> <BR>ONE OF...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Homely 4BR with 2 Master Suites, Kissimmee1 / 40
    (8)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Washer
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We rented this home for a volleyball tourney at the OCCC. There were only 4 of us, so this was much more of a house then we needed. First, the pictures are actually pretty...
    Reviewed April 8, 2017
    We were in awe of this home. Beautiful home setting. Was close to Disney. Wasn't as close to the beach as I thought, but wasn't an issue driving. We will be planning on staying...
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    About this property
    Ready to have your dream Florida vacation? You're gonna need a dream house!<BR><BR>This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme privacy and maximum fun! From here...
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    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    LAKESIDE HAVEN, Windward Cay, The "hidden jewel" of Kissimmee1 / 15
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Washer
    • Private Outdoor Pool (Heated)
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    • Waterfront
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This is a really lovely 3 bedroomed villa which is extremely comfortable and well equipped (including rain ponchos, which we needed lots!) the pool backs onto a lovely lake so...
    Reviewed 4 weeks ago
    Me and my family had a fabulous time staying at the villa. The villa had everything you could wish for and was extremely well equipped. We loved the homely touches and the BBQ...
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    About this property
    Our beautiful, spacious fully air conditioned private villa is located on a fantastic large plot with fantastic views over a large lake and in the peaceful community of Windward Cay 'the hidden jewel of Kissimmee' and yet less than 1 mile from the 192 with all the shops,entertainment and...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spacious Bellair Villa includes a Terrace,Gameroom1 / 87
    (9)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Hot Tub
    • Balcony
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2015
    Stayed here with my friends from out of the country for my wedding week,and I must say it was an awesome experience,the house and rooms were clean and spacious. The rooms and...
    Reviewed August 17, 2015
    Perfect for our large of 13 (3 families). Great value villa which was perfect for what we needed. We all enjoyed the pool and games rooms. Plenty of room having six bedrooms...
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    About this property
    Special deal, book and pay for 14 nights and get 1 night free or book 21 nights get 2 nights free. please contact owner to organise. Free night/ nights can be used for an early check-in or late check -out giving flexibility when booking flights.Longer stays please inquire for a discount. This home...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Special 200 in MARCH/APRIL! 179 in MAY/JUNE INCLUDES POOL HEAT!1 / 27
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
    • Washer
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    • Children's Pool
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    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 4, 2016
    The house was amazing, it had everything we needed and plenty of space. Paula was wonderful about addressing any questions we had. We will be staying again for sure. Our family...
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    About this property
    Private gated community with Beautiful Club house. No one comes close to the Paradise Palms amenities. Our house sits on a corner lot only one block from the clubhouse. Featuring a private pool and Jacuzzi in a screened lanai with seating for dining.When entering the front door you are greeted...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Disney & Minions Modern 4 bed decor close to parks1 / 27
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed March 20, 2017
    The location is amazing! This is a great family-friendly condo with a stunning pool and wonderful kitchen. The stay was wonderful !!! I'll love to visit again!
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    About this property
    Comfortable home for your family to enjoy your Disney vacation! Townhouse with private pool near Disney. Sleeps up to 8 people. 4 bedrooms and 3 bathrooms, 1 suite. All bedrooms have TV. 1st FLOOR: - Tiled floors in the 1st. floor, except for the bedroom. - 1st bedroom with king size bed and TV. -...
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    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spacious 7 Bedroom home at Bella Vida1 / 24
    (1)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    Smoking allowed
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Windsor Hills - Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay you will enjoy this well appointed home...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Donald Duck's Condo1 / 66
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 16, 2017
    Had a great time in this well-equipped, comfortable condo & enjoyed the leisure facilities on site. Stayed here as it's a fabulous location for Disney! Would definitely book...
    Reviewed July 12, 2016
    We had a great time. My son played in the Nationals at the Convention Center. I was so so happy the condo was around the corner from the teams' condo. I really couldn't ask...
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    About this property
    In sunny Orlando/Kissimmee Florida, location is everything.....and we are located the very closest to Disney......less than two miles to the main entrance! Each evening, you may enjoy the breath taking view of Disney Fireworks from the Windsor Hills Resort area. We are also less than two miles to...
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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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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    "Imagine You and Your Family Renting this Beautiful 5 Star Luxury Villa Overlooking The 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....
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4460 GH1 / 30
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed April 25, 2017
    I will definitely be booking with Homestead rental homes when we travel back to Orlando in the future! Great company to stay with!
    Reviewed August 8, 2015
    Just returned from a one week vacation with my family. Liked Best: private fencing around the pool area, spacious, comfortable bedding, nice decorLiked Least: noise from the...
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    About this property
    4 Bedroom, 2.5 Bathroom Sleeps 8 people Master with En-suite Bathroom: King Size Bed Bedroom 2: En-suite Bathroom: King Size Bed Bedroom 3: 2 X Twin Size Beds Bedroom 4: 2 X Twin Size Beds South facing pool Fenced in back yard Newly remodeled, all new furniture, deluxe mattresses Gourmet Kitchen,...
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    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    LAKE VIEW Compass Bay Condo,luxury & Gated,699$p/w1 / 48
    (30)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
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    • Waterfront
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    Just left after a 6night stay. The house is amazingly beautiful and the location is perfect!! In the center of everything. Shopping ane parks are all near so for that I give...
    Reviewed November 30, 2016
    It is a very nice home and well located for Disneyworld; owner Rose was kind and corrected any issue accordingly.
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    About this property
    Truly a cut above the rest. Exceptionally stunning and professionally furnished private town home in one prestigious gated community,one of Orlando's most beautiful destinations. Just built in 2010,our unit have 3 bedroom,3 bathroom. My town home is the superb home away from home for up to 8...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    About this property
    FABULOUS 6 BEDROOMS HOME WITH POOL, GOURMET GRILL AND GAME ROOM Property Type: Single Home Floor Area: 3200 sq ft Location: Bella Vida Resort, Kissimmee, Disney Area Discover your escape from the ordinary to the spectacular with this fully loaded 6 bedrooms/5.5 bathrooms vacation home. You'll find...
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    Kissimmee, Central Florida 34746
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Three stories of luxury living are yours to enjoy in this newly renovated estate home in Legend's Corner overlooking the 10th tee and future clubhouse of the Signature Jack Nicklaus Tradition Course. With over 5,600 square feet of living space, everyone can spread out and enjoy all that this home...
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    Kissimmee, Central Florida 32805
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This luxuriously appointed villa is beautifully presented with upgraded furniture and fittings throughout and fully air conditioned to create a comfortable indoor climate With 2 bedrooms and bathrooms located on the ground floor it is an ideal choice for groups with elderly or less mobile members...
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    Kissimmee, Central Florida 34758
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    Fantastic Kissimmee Home and only 20 min1 / 59
    (24)Excellent
    Downtown Kissimmee
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    My wife and I stayed here in October. I did submit a review earlier but somehow Trip Advisor seem to have lost it!We have stayed in the area before, so we knew where we were...
    Reviewed February 1, 2017
    Location was perfect, close enough to the attractions but far enough away from the busy tourist-filled streets and resorts. The home was absolutely beautiful. Cannot wait to...
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    About this property
    The home is a 3 Bed town home at the Trafalgar Village Resort which is located on Poinciana Boulevard just 10 minutes south of highway 192 and approx 15 – 20 minutes to Disney.<BR>The home has been furnished to a very good standard and has a King, and two Queen bedrooms. <BR>There is wifi internet...
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    Location Information
    Kissimmee, Central Florida 34758
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Wilderness Lodge is a large premier villa located in the beautiful Emerald Island Resort. It has a south facing private pool plus spa with amazing views over a beautiful lake and woodland conservation area. The Emerald Island Resort is one of the closest to Disney World, yet secluded enough to...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    4bedrooms, 15minutes from DisneyLand Family House!1 / 28
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2017
    We loved this vacation rental. Close to resort pool which is beautiful, my kids LOVED it. We also had our own private pool which was heated perfect. There is a lake right out...
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    About this property
    Welcome to our, beautifully decorated, luxurious 4 bedroom, 3 bath vacation pool home. Featuring a private heated pool, 15 minutes from the theme parks, our home has everything you need to enjoy a great vacation with all of the comforts of home. The kitchen is fully equipped. All of the bedrooms...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Kissimmee Flight and Weather Info
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    Orlando Intl Airport
    10.4 miles from Kissimmee
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    Additional Kissimmee Info

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    • Local time: 10:26 AM (EDT)
    • Peak travel: March - April
    Kissimmee Vacation Rentals

    Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

    Kissimmee Vacation Rentals for Families

    More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

    Advantages of renting a vacation home in Kissimmee

    Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

    Rent a vacation house with a pool in Kissimmee, Florida

    How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

    Rental deals in Kissimmee

    Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

    Kissimmee and Orlando beyond Disney

    Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.

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