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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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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Beautiful 7 BEDROOM LAKEFRONT ORLANDO/DISNEY HOLIDAY VACATION HOME1 / 44
    (11)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    8 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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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    Beautiful 6 bedroom Home1 / 36
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 2017
    This property is more than what the pictures show. Recommend you pay the extra $ for the heated pool and hot tub. Worth every cent! Peaceful neighbor hood, with the most...
    Reviewed September 14, 2016
    The house was great!! Lots of room! Comfortable beds! They even had some toys and games for the kids. Only thing I would say is get the heated pool because without it you don't...
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    About this property
    Beautiful 6 bedrooms 5 bathrooms home near Disney World, this luxury home is located in the secure resort of Trafalgar Village and is just 15 minutes away from Disney Attractions. This home has 6 bedrooms, 5 bathrooms and a private screened in pool area with a spa/Jacuzzi. The kitchen is fully...
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    Kissimmee, Central Florida 34758
    Rental Home - 6 Bedrooms, 5 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)
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    • 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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    Family Retreat - 7 Bedroom Vacation Home1 / 29
    (1)Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Incredible vacation property minutes away from Disney, Universal Studios and other Orlando attractions. Home features unbelievable amenities such as a plasma TV, TVs in every bedroom, and a game room with a 42' LCD TV home theater system, pool table, standup arcade games and more! You will also...
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    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    A hideaway dream - an amazing spacious family home1 / 45
    (2)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 yesterday
    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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    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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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 15
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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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    Avenant's Castle1 / 20
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 2017
    Well as i stated in my sentence this is really a castle, every thing was nice and perfect very clean and all that was advice in the add was inside, thanks David for letting us...
    Reviewed December 2, 2016
    This was the best vacation spot ever. It was very clean and welcoming. We will be back in the future.My family really enjoyed our vacation.
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    About this property
    Welcome to Avenant's Castle located in Emerald Island Resort, an exclusive manned gate community. This home was remodeled in June of 2015. We upgraded this home to be one of the most beautiful homes within 3 miles of Disney. Murals by the areas best artist are throughout the home - your kids may...
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    Kissimmee, Central Florida 20878
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
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    Reviewed 2 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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    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
    • Satellite TV
    • Air Conditioning
    • Children's Pool
    • DVD Player
    • 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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    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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    4460 GH1 / 30
    (4)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    his vacation home was renovated recently. We put lots of efforts to keep our house at the top of the line. We sincerely welcome all of our guests and feel honor to have your unforgettable memories in our house. It has 3 King Bedrooms, 2 Queen bedrooms, 6 Twin Beds in 3 kid rooms, 4.5 bathrooms,...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Windsor Hills,own cinema room, Xbox one, free WiFi1 / 54
    (8)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 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...
    Reviewed May 7, 2017
    Superbly located with shops/supermarkets within 5mins drive and Disney parks 15mins away. We were 2 families staying at this property. The house was a great size with...
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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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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    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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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    New TownHome 4/3+Pool / Gated Resort / 5 m Disney1 / 35
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Shared Yard
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2016
    Unfortunately I'm a 36 year old mom of three with less than a year to spend making memories. I spent a lot of time looking and researching the best deal for our family of five...
    Reviewed May 2, 2014
    1st of all the Property Management were amazing, they prepared everything for us, It was like having a personal concierge. They really help us from the beginning of choosing a...
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    About this property
    Brand New Town Home with 4 bedrooms and 3 Bathrooms, one Bedroom and one bathroom downstairs. Private pool, optionaly heated. Located 5 miles from Disney World MainGate. Close to shops, restaurants and all you can need. The Paradise Palms Resort is top of the line with a big pool with cascade,...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    • Washer
    • Private Outdoor Pool (Heated)
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    • Patio
    • Grill
    • Wi-Fi
    • 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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    Brand New South Facing Lake View 8 BR/6BA Home with Pool/Spa, Game Rm, Wifi1 / 29
    (2)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Satellite TV
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 2017
    Our group of 16, ages 3 months to 87 years old absolutely loved this rental home! It was our first time renting and we were nervous to break the habit of staying in Disney...
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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 stunning LAKEVIEW, heated SOUTH-FACING pool and Jacuzzi. Game room with seating, pool table and...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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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
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days 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 3 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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    Tennyson Villa in Kissimmee close to Disney1 / 26
    (11)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2016
    Lovely stay at Tennyson which is perfectly located, and is very spacious and homely.The owner Jane is very helpful, and the facilities within the villa are top...
    Reviewed June 6, 2016
    As a group of 4 adults and 1 child (6 years old) we spent an awesome 12 days at this villa. Location is perfect - very close to Disney, Sea World and Universal all of which can...
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    About this property
    Please contact owner to confirm quoted price. Bookings over 7 nights cleaning fee is deducted form price. My home is managed and looked after by myself and a professional management company in Kissimmee. Thank you for checking out our home. Lovely well maintained spacious private 5 bed family villa...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Homely 4BR with 2 Master Suites, Kissimmee1 / 40
    (7)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
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    • Washer
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    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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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Mufasa's Pride - Military / Police / Fire Special1 / 73
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Everyone had a wonderful time. The space was very lovely. Very close to stores. Very convenient for the family.
    Reviewed August 3, 2016
    Excellent Vacation home. This home has everything you need to enjoy your vacation, plenty of room for entire family. Home is very well kept . i do recommend that the property...
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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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    Dolphin Villa - Doral Woods, 5* rated with Wifi & Games1 / 56
    (27)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 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...
    Reviewed February 21, 2017
    We primarily picked this property because of the privacy of the back yard. It's not like a lot of properties in Florida where your house and pool are intimate to your neighbors...
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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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    Location Information
    Kissimmee, Central Florida 34758
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Downtown Kissimmee
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 BR / 2 BA Pet Friendly Pool Home close to Disney1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Satellite TV
    • Air Conditioning
    • Private Yard
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 16, 2016
    This is my second time staying at this rental and both times it was convenient and a great deal. The location was located close enough to Disney we were able to take a Lyft ride...
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    About this property
    This three bedroom home is just what your family needs for that memorable vacation in Central Florida. Sleeps up to eight in your party. It has a King, Full and (2) Twin size beds. This home is located in Indian Wells which is located literally five minutes from the gates of the Disney parks. The...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7 Bedrooms, 6 Bathrooms, Sleeps 17 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book this luxury 7-bedroom, 5.5-bathroom vacation rental house for your next Central Florida getaway! Located just 6 miles from Disney World, this stunning villa sleeps 17 guests and is ideal for multiple families or a large group sharing a memorable retreat! Recently updated, this spacious 3,000...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 17
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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
    • Washer
    • DVD Player
    • Grill
    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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    Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 101 / 17
    (22)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Hot Tub
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The house was great but not sure if the pool was working properly but it was not a big deal. The house was very spacious and had more than enough room for everyone. The location...
    Reviewed 2 weeks ago
    OMG THIS PLACE WAS JUST AS I IMAGINED IT TO BE ..my family really enjoyed themselves the only thing was the game room needs to be updated. I will book again and tell friends and...
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    About this property
    Welcome to our home on Seasons. It is a St Vincent model built by Park Square Homes and is 2765 Sq. Foot of Executive quality. It is a luxurious 5 Bedroom – 4 Bathroom Villa, which has 2 Master Suites and 3 other Bedrooms - which comfortably sleep 10 with ease, a Private Pool and spa plus a well...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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)
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    • 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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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Sauna
    • Shared Indoor Pool
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    • 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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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
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    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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    Simba's Magic Villa by Emerald Island Rentals1 / 39
    (4)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Hot Tub
    • Washer
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 1, 2015
    Very nice and incredibly spacious home for our family during our stay at WDW! VERY close to the Parks!!
    Reviewed May 23, 2015
    Stayed here with 10 grandkids and six adults for 8 days. Very clean home with plenty of rooms for all 16. Nice enclosed pool and game room. Bring your own TP , paper towels or...
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    About this property
    A 7 bed/4.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned theater/game room and a south-facing pool/spa. With 2 king master suites, 2 queen bedrooms, 2 themed kids rooms with two twins each and another room with 2 bunk beds, this villa can...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Orlando Vacation house with Boat/RV parking1 / 35
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • DVD Player
    • Hot Tub
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2017
    This place was a great get away for our family of five. It was really clean an modern place. We loved the pool and how quiet it was. The owner give you step to step on how to...
    Reviewed August 12, 2016
    best house ever been i love the pool the are where the house are located i just love everything nice weather and clean house
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    About this property
    Come and enjoy Kissimmee, Florida! This beautiful home is located off Neptune road two miles away from Downtown Kissimmee and one mile away from the Florida Turnpike exit. This property is located in a private ½ of acre lot making it perfect for someone traveling with a boat, travel trailer or...
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    Location Information
    Kissimmee, Central Florida 34744
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Air Conditioning
    • Private Yard
    • Secure Parking
    • Washer
    • Wi-Fi
    • 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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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Private Outdoor Pool (Heated)
    • Air Conditioning
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    Suitability
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    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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    4bed/3bath home in Bella Vida Resort! 951LF1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Shared Indoor Pool
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2016
    Wonderful Stay and good equipment. good location. good services and cleaning. I'd recommend a reservation
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    About this property
    Delightful townhouse with 4 bedrooms and 3 bathrooms, located just 10 minutes from Disney Parks! This lovely home has a large living space. If you are looking for the perfect base for your Florida holiday, then look no further than this amazing 4 bedroom home. Set on the side of a beautiful lake...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sonoma Resort is a brand new vacation rental resort located next to "The Loop", a premier shopping and entertainment mecca, jut 10 minutes from Disney parks, as upscale brand outlets, malls and numerous championship golf courses. The resort offers Sonoma offers exceptional amenities to include a...
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    Location Information
    Kissimmee, Central Florida 34741
    Condo/Apartment - 10 Bedrooms, 8 Bathrooms, Sleeps 20
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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
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    • 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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    Grand Opening! luxury Disney Villa for large group1 / 30
    (1)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Children's Pool
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    • Housekeeping Included
    • Satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2016
    The home was very spacious and beautifully decorated. We had a large group and everyone was comfortable. Booking the home was easy, and Tracy was very accommodating. I would...
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    About this property
    This luxurious brand new vacation home is located in the Windsor at Westside, a prestigious resort community - with short drive to DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. The 4382 sq. ft. living space is professionally furnished with upscale...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 6 Bathrooms, Sleeps 22
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    Downtown Kissimmee
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The new Storey Lake resort is in one of the best locations of the city, just 10 minutes from Disney Parks, 5 minutes from Lake Buena Vista Outlet and convenient access to nearby shopping, dining and entertainment. The homes, from 4 to 6 bedrooms that can accommodate comfortably up to 12 people, are...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Central Heating
    • Washer
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    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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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Yard
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 4 Bed 2 Bathroom villa has been furnished to a very high standard and benefits from a beautiful lakeview. The villa can sleep up to 10 guests. The villa has a beautiful lake view on the 5 Star Lake Berkley Resort, which is safe, secure and with a gated entrance 24/7. There are 2 sitting rooms...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Waterfront
    • DVD Player
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    • 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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    Scotsman's Retreat1 / 70
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Balcony
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2015
    We stayed here for eight night's with two family's, having four children all the ensuites really helped especially when trying to get ready in a morning with teenagers!.We have...
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    About this property
    Scotsman's Retreat is a beautiful and quiet 2 storey 5 bedroom house house on Cumbrian Lakes which is a relatively new gated community build in a conservation area and, as the names suggests, based around 3 large lakes. The villa is situated in an ideal location with an extended pool deck with a...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look no further for your perfect "magic" holiday here at Magic Villa situated within the luxurious Emerald Island Resort. This spacious villa has been refurbished to a luxurious standard, which provides everything you could possibly need for a relaxing, stress free stay, on the doorstep of the...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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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: 07:52 PM (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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