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Holiday Rentals in Kissimmee, FL

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    Travellers to Kissimmee are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 66
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Luxury-2101 SqFt 5BR/3BA-Private Pool/Spa-7 HDTV's-10 Miles to Disney-Video Tour I am getting multiple inquiries daily asking if we have have availability for dates already booked on calendar. I update calendar daily. Please check calendar before emailing or calling asking about availability.... View all property information
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    Kissimmee, Central Florida 34758
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Kissimmee, Central Florida 34747
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The two story Villa is on a small development located centrally to the area attractions (Disney, Epcot, Universal Studios, Seaworld etc) and close to International Drive. Orlando and the airports are only a short drive away. The development is mostly residential. The first floor consisting of... View all property information
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    Kissimmee, Central Florida 34746
    1 / 21
    4 Bedrooms, Sleeps 8 | Quick View
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    About this property
    This comfortable townhome in BellaVida Resort features a large master bedroom, a private lounge pool and patio, 3 Smart TVs in bedrooms, a Large 55' screen LED TV in Living Room as well as a DVD/Blu-Ray player and Roku Streaming. There is also a fully equipped kitchen, dining area, Wi-Fi access-... View all property information
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    Kissimmee, Central Florida 34746
    1 / 32
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    'Imagine Renting This Stunning Villa In One Of Orlando`s Most Prestigious Resorts, Windsor Hills, with it's own Private Pool and Games Room' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The... View all property information
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    Kissimmee, Central Florida
    1 / 22
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Stunning 6-bedroom Windsor Hills Resort vacation home with 2 suites, 3 themed custom designed bedrooms, game room and luxury screened private pool (southwest facing) & spa with safety fence, furnished patio with extra large lanai, fine furniture throughout the house, ceiling fan in every room,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Emerald Island is a gated community and is manned 24 hours a day. There is a club house with a small shop ,games room ,computer room and a gym , there is large pool and tikki bar, where you can enjoy meeting other people. There are shops near by and many very good restaurants . There are tennis... View all property information
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    Kissimmee, Central Florida 00
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    1 / 32
    3 of 5 bubbles (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Kissimmee vacation rental home in a beautiful gated community with 4 bedrooms, 3 Full Bathrooms, Private Pool with Lanai, Outdoor Shower, Patio Furniture & a lovely lake view. Big Screen TV, High Speed Internet, Games Room and full size Pool Table. TVs in 3 bedrooms, Family Room and Loft space.... View all property information
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    Kissimmee, Central Florida 34746
    1 / 31
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This fully air conditioned luxurious open plan villa with high vaulted ceiling giving a cool fresh feel in the summer months. It has a tiled floor through the lounge, dining room and kitchen area. carpets in all the bedrooms. In the master bedroom there is a king size bed with an en-suite. bedroom... View all property information
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    Kissimmee, Central Florida 34746
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This single story superior 4 bedroom, 3 bathroom pool home is located in the quiet community of Magic Landings, situated on Highway 192, which ideally located for those who want a perfect vacation. Both master bedrooms not only have ensuite facilities they also have patio doors leading to the pool... View all property information
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    Kissimmee, Central Florida 34744
    1 / 36
    4 of 5 bubbles (1) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villas at Seven Dwarfs is in a superb resort community and offers first class accommodation. After the parks, bask in the sun at the pool and spa, play a game of Tennis or stroll the beautifully manicured grounds while the kids play some games at the recreation center. The resort is ideally located... View all property information
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    Kissimmee, Central Florida 34746
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Shared Garden
    • Grill
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    • Balcony
    • Terrace
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    • Pet-friendly
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    • x
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    About this property
    Please note these Check-in Day Requirements for this property: Feb 01 - Apr 30 : Saturday check-in required, Saturday check-out required. This unit accepts only saturday to saturday bookings. That means check in on a saturday, and check out on a saturday. All other non saturday to saturday... View all property information
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    Kissimmee, Central Florida 34747
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Steps from one the Pool 2 & minutes to another! Close to Golf Courses and Legoland! - 40 min to the Disney / Universal! Main Floor 1218Sq Ft - 3 Bedroom, 2 Bathroom, (Queen/Dbl/Twins + Sleeper Sofa - sleep up to 8!) Park directly in front of your unit! In-suite Laundry, New Floors, New LCD... View all property information
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    Kissimmee, Central Florida 34759
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Compass Bay is one of the nearest communities to Disney. Within 5 minutes of leaving Compass Bay you will drive pass 'Welcome to Disney World" sign The whole of Disney property is then open for you to enjoy. Perhaps a day at Magic Kingdom or Epcot. The choice of 4 Theme Parks or two water parks... View all property information
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    Kissimmee, Central Florida 34746
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    About this property
    I rent my condo in Orlando - Florida. Location directly from the owner. Condo fully furnished and sleeps 8. Chek in/out is in friday, saturday or sunday for 7 days. Availability : 23 december to 30 december 2016. You can choose another week but the availability has to be confirmed with the ressort.... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This 4 bedroom vacation house has it ALL. It can fit two families (8-10 people) This model features a spacious single story open floor plan, and a screened-in private pool With beautiful ceramic tile throughout the home and soft carpeting in each of the bedrooms, this home is sure to be... View all property information
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    Kissimmee, Central Florida 34758
    1 / 100
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our beautiful townhouse is located in the gated community of Venetian Bay Villages, with a guardhouse that is manned 24/7 and additional security patrolling the area, Venetian Bay is one of the safest places to stay and conveniently located: 15 minutes from Disney World, 20 minutes from Sea World,... View all property information
    Location Information
    Kissimmee, Central Florida 34741
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    1 / 39
    4.5 of 5 bubbles (2) Very good
    5 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Named HGTV’s Number 1 Vacation Home and seen on “House Hunters,” this exceptional 5 bedroom estate home overlooks the 11th hole of the signature Jack Nicklaus Tradition course. The expansive 5 bedroom home comes with 5 full bathrooms and 3 half bathrooms. Featuring three master suites, all with LCD... View all property information
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    Kissimmee, Central Florida 32805
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Private Garden
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    • Pet-friendly
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    • x
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    • x
    About this property
    Your family is sure to enjoy the amenities of this beautiful community. Relax by the heated Resort swimming pool and Jacuzzi spa. Grill out and have a family picnic and a competitive game of sand volleyball. The community center features an exercise room and gathering place. Enjoy the sunshine and... View all property information
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    Kissimmee, Central Florida 34747
    1 / 20
    4.5 of 5 bubbles (19) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The home is a beautifully furnished and spacious property, well-maintained by our Management Company. <BR>It is situated off Highway 192 in the prestigious Emerald Island Resort, one of the premium vacation communities in the area, a tropical oasis nestled within protected wetlands with... View all property information
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    Kissimmee, Central Florida 34747
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This wonderful and spacious 4 bedroom 3 bathroom home is situated in Indian Creek, a quiet community based just off the 192. This home can sleep 8 people, is just 10 minutes from the gates of Disney and is close by to local shops, restaurants and much more. The home boasts a beautiful oversized... View all property information
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    Kissimmee, Central Florida 34747
    1 / 19
    5 of 5 bubbles (42) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Our beautiful and spacious 4 bedroom, 3 bathroom villa is situated within the Indian Creek Community in Kissimmee, one of the few villa communities that are genuinely close to Disney in Orlando, Florida. In our case we are only 3 miles to the nearest Disney park, Animal Kingdom and the gates to the... View all property information
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    Kissimmee, Central Florida 34747
    1 / 57
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    This Upscale Vacation Home has everything, at over 3400sq ft of space there is more than enough room for even the largest family gathering to have their own personal space. The screened sun deck is amazing and has the best uninterrupted view of the Lake, where you will see plenty of birds fly over... View all property information
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    Kissimmee, Central Florida 34746
    1 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Enjoy the family vacation that you have always dreamed about! While enjoying the various amenities in our vacation villa that we proudly share with your family, our features fit for royalty include: -Private True South facing pool with all day exposure to our beautiful sunshine -Hot Tub/Jacuzzi... View all property information
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    Kissimmee, Central Florida 34747
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Westgate Vacation Villas is situated just minutes from Disney. The apartment is in a quiet location on the site which has plenty of amenities. This is a loft conversion unit with two single beds and is a favourite with children. It has one master suite with bath and shower,, one bedroom with two... View all property information
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    Kissimmee, Central Florida FL34747
    1 / 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This 4 bedroom 3.5 bathroom vacation villa is the perfect location for your family vacation - whether you are visiting Florida for the golf, shopping or the theme parks! The villa is within the gates of Remington Golf and Country Club. On entering this spacious villa it is apparent that the owners... View all property information
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    Kissimmee, Central Florida 34744
    1 / 32
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This home has it all! The fully equipped kitchen makes cooking at home a breeze! This kitchen offers bar seating and a breakfast nook, so everyone can share a meal together. The formal dining room is a great place for the whole family to sit together and make family memories. There is a highchair... View all property information
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    Kissimmee, Central Florida
    1 / 51
    8 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • x
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    About this property
    This BRAND NEW 8 bedroom 7 bath encore reunion luxury home is 6 miles away from Disney World. Situated in a highly sought after Liberty Bluff neighborhood and it is perfect for families wanting a comfortable and luxury vacation. With a fully equipped kitchen and two king bed suites downstairs and... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    6 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    • x
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    • x
    About this property
    New 6 bedroom Home -5* resort, 2.5 MILES to DISNEY, Heated Pool/Spa, Games room, Extended Deck, Premium Lot, Pool facing beautiful green area. Resort has Lagoon style pool, Cinema, store,water slide, children's play areas, fitness center, games room. 2 Kings with private Bathroom , 1 Queen with... View all property information
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    Kissimmee, Central Florida 34747
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Disney private vacation condo, ground floor unit, in the beautiful resort of Windsor Palms, a private gated community with tons of amenities included, only 3 miles to Disney and other attractions. 3 BR/2 bath luxury with private heated Olympic size pool/Jacuzzi/ game room at the club house, with... View all property information
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    Kissimmee, Central Florida
    1 / 24
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    "Imagine Renting This Stunning Villa In Orlando`s Most Prestigious Resort, Windsor Hills" This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa has every luxury with A PRIVATE POOL, Spa,... View all property information
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    Kissimmee, Central Florida
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Windsor Hills Resort is only a 25 minute drive from the Orlando International Airport, and is situated central to all if Orlando's famous attractions. The resorts amenities include gated community, water park with Olympic Size Swimming Pool, fountains, waterslides, spa, separate toddler pool,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 18
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Located in the beautiful gated community of Bella Vida Resort, this awesome 6 bedroom home is perfect for large families wanting a simply perfect vacation getaway. The home feels spacious from the moment you open the front door. There's a large sitting area where you can lounge with a favorite... View all property information
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    Kissimmee, Central Florida 34746
    1 / 42
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    “Imagine you and your family renting this beautiful 5 bedroom Villa located on Reunion Resort. This luxury 5 Star Villa has it’s own private pool. It’s only 10 minutes from Disney World” This villa is situated in the exclusive resort of Reunion, only 6 miles from Walt Disney World and all the major... View all property information
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    Kissimmee, Central Florida
    1 / 37
    5 of 5 bubbles (4) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 22 | Quick View
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    • x
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    About this property
    As a recent guest described it, we "have the best homes for kids in all of Orlando"!!! (Yes, your many hours of hunting down the perfect vacation property are finally over! Our guests prefer our property over the Disney Resorts, too!) Come stay at this amazing luxury playhouse! 4 Luxurious King... View all property information
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    Kissimmee, Central Florida 34747
    1 / 19
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    This home has 3 masters, with queen sized bed and en-suite bathroom. Two masters downstairs and 1 upstairs with the other 2 bedrooms. The fourth bedroom has bunk beds and the fifth bedroom has two twin beds which share the 4th bathroom. All Bedrooms have their very own Flat screen TV's. Very... View all property information
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    Kissimmee, Central Florida 33897
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Can get you two or three bedroom condo anywhere you would to go for a very good rate. Weeks run from fri to fri or sat to sat or sunn to sun. Please let me know what you are looking for. Thank you Rick. View all property information
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    Kissimmee, Central Florida 34746
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    7 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • DVD Player
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    This 3500sq/ft villa includes the following amenities: - 7 Luxurious Bedrooms (2 King, 3 Queen, 2 kids room) - Loft with Queen Sleeper sofa - 5 Bathrooms - Fully equipped kitchen - Spacious sitting and dining area - Games room - Private Pool and Spa in screened lanai - Gas BBQ Grill -... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    AmAn, our privately owned 4-bedroom, 3-bath pool home is located in Terra Verde, one of the most sought after resort communities. Our home will provide you with the space, privacy and luxury you are looking for while on vacation. AmAn is just a few minutes drive from Disney World, within short... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This beautiful home on The Sanctuary at Westhaven is a real delight. Tastefully furnished throughout, living room comprises 2 sofas, one of which converts into a double bed..! The dining room has a large table and seating for 6. The family room features a 46 INCH LCD HDTV. Choice from over 200... View all property information
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    Kissimmee, Central Florida 33896
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Property Reference #RVH_156 Whisper Way King of Comfort  - 3 Bed 3 Bath Reunion Resort Condo This large 1,755 sq ft luxury condo located close to the center of Reunion offering convenience and luxury in a peaceful landscaped setting. Located on the second floor with elevator access this corner unit... View all property information
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    Kissimmee, Central Florida 34747
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    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • x
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    Holiday Lettings Special: Free Pool Heat October through May (Spa heat is always free).<BR><BR>Be sure to click the link below to the homeowner's site for more details, a floorplan, more pictures and lots more information. (below where it says 'CLICK HERE - Disney Vacation Home Owner's... View all property information
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    Kissimmee, Central Florida 34747
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Welcome to our 5 bedroomed villa,unwinding and relaxing in the south facing swimming pool, Our villa boasts many comforts to make your stay a memorable stay. We have lcd televisions in all 5 bedrooms, lounge, all with cable,internet enabled with router/wi fi, dvd players to 2 of the bedrooms and... View all property information
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    Kissimmee, Central Florida 34744
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    Large 3,275 sqft. home with private pool and resort amenities. Just minutes from Walt Disney World with all the comforts of home with fully equipped kitchen, flat screen Tv's, washer/dryer, garage, private pool, and privacy for your whole family. Lots to do in Paradise Palms Resort with great... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Kissimmee, Central Florida 34747
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    6 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    The Perfect Hideaway Villa is a fully alarmed 6/bed (sleeps up to 13 + cribs available ) 4/bath pet free luxury villa in the 24/7 gated 5* Windsor Hills Resort, situated on an elevated plot offering panoramic lake and conservation view from the large private pool and spa deck where you can relax in... View all property information
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    Kissimmee, Central Florida 34747
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    9 Bedrooms, 5 Bathrooms, Sleeps 30 | Quick View
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    This beautiful new 9 bedroom villa is one of the largest villas available for rental in the Disney area. This villa spans over 3800 sq/ft of professionally furnished decor and furnishings. First Floor: The property features 9 bedrooms and 5 baths. On the ground floor you will enjoy one master suite... View all property information
    Location Information
    Kissimmee, Central Florida 33896