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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.
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    5 Bedrooms, Sleeps 12 | Quick View
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    About this property
    Floor Plan (The Seville) 2,336 sq. ft 2 story home with pool and spa (South-West facing pool) We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home... View all property information
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    Kissimmee, Central Florida 34747 2124
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    We welcome you to come and experience our luxurious condo home located at the most prestigious 5 vacation resort The Windsor Hills Resort Featuring a 24 hr secured gated community only 2 miles to the Disney World Condo is fully furnished with 5 amenities to ensure a great vacation for every age... View all property information
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    Kissimmee, Central Florida 34747
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Children's Pool
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    Our condo is located in Kissimmee within the community of lighthouse Keys It is constantly in the top two for accommodation in the area on trip advisor. Ultimate in luxury and can sleep 6 comfortably and up to eight. Perfect for family holiday, golf trip. Fifteen minutes away from the all the... View all property information
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    Kissimmee, Central Florida 34747
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    Floor Plan (The Spencer) 2,382 sq. ft 2 story home with pool and spa (South facing pool) We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with... View all property information
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    Kissimmee, Central Florida 34747 2124
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    5 of 5 stars (6) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    About this property
    This villa is furnished to a high standard throughout. The bright & spacious rooms provide plenty of room for the whole family. The highlight has to be the lovely south-west-facing pool – the perfect spot to unwind at the end of a long day enjoying Orlando's many attractions. The extended lanai... View all property information
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    Kissimmee, Central Florida FL 34746
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our family owned Orlando vacation spot is conveniently located four miles from Walt Disney World in the private residential area of Lindfield Estates in Kissimmee, Florida. There is fun for the whole family to enjoy! You're only a hop, skip and a jump away from all the Disney theme parks including... View all property information
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    Kissimmee, Central Florida 34747
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our beautiful, luxury, fully air-conditioned, Disney villa is located within the première resort of TRAFALGAR VILLAGE, Kissimmee; an up-scale community based around luscious woodland and lakes and just 15 minutes from the gates of Disney. The Villa has 4 bedrooms, all with TV, 3 bathrooms a... View all property information
    Location Information
    Kissimmee, Central Florida 34758
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This quaint town house is tastefully decorated and furnished to a high standard. With light and colorful carpets and furniture it really gives you a fresh feeling.Enter through the front door to pass the kitchen and dining area.The kitchen has a breakfast area that seats up to six people, while the... View all property information
    Location Information
    Kissimmee, Central Florida 33746
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Mickey's Holiday Hideaway Villa is located in the Five Star rated gated resort community of Windsor Palms and contains 4 Bedrooms and 3 Bathrooms and is furnished and equipped to a very high standard. Bedroom Configuration: 1 King Master Bedroom with en-suite, 1 Queen Master Bedroom with en-suite... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 stars (21) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The house is a typical florida town home with views onto woodland from the outside patio and 1st floor master bedroom balcony. It is very comfortably furnished and has everything you need for a happy home from home holiday. 3 miles from the entrance to Disney makes it ideal for those wishing to... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Indoor Pool
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    About this property
    You Will Enjoy A Private Pool, Proximity To The Parks And FREE High Speed WiFi!! This beautiful new home is tastefully decorated with plenty of space for the whole family! Living Room is spacious and features a Flat Screen TV. Dining Area sits 6 people. Kitchen is fully equipped with brand new... View all property information
    Location Information
    Kissimmee, Central Florida 34746
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    • Balcony
    • Terrace
    • Waterfront
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    About this property
    Westgate Town Center Resort & Spa in Kissimmee, Florida, provides guests all the comforts of a fully furnished home with accommodations ranging from studios to spacious four-bedroom villas, all within minutes of Orlando's world-famous theme parks and attractions. With a variety of onsite amenities... View all property information
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    Kissimmee, Central Florida 34747
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    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tropical Beauty Villa is a tastefully furnished and well maintained pool villa boasting 1800 of air conditioned Floridian Luxury. The accommodation has 3 bedrooms, family bathroom, en-suite with walk in shower and a corner bath tub, fully fitted kitchen. If you love sunshine, you will love the... View all property information
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    Kissimmee, Central Florida 34746
    1 / 99
    4.5 of 5 stars (7) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This family friendly, roomy and airy villa with private (heated) pool is well equipped and stylishly decorated to a very high standard. Local shops and restaurants are just minutes away. Disney, SeaWorld and Universal theme park complexes are all within easy access (20 mins or less approx).... View all property information
    Location Information
    Kissimmee, Central Florida 34744
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Overview This 5BR house is fully furnished and features a good taste decor. You will feel as comfortable as you do in your own home and, at the same time, will take advantage of luxury and amenities you would have in a hotel. The kitchen is fully equipped with cooking utensils, refrigerator,... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
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    • x
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    About this property
    Your DISNEY dream vacation starts here. 10-15 minutes from all the attractions. BED AND BREAKFAST FLORIDA DREAMS VACATIONS are renting BEDROOMS for an amazing stay. PRICE PER ROOM. Perfect for singles, couples or families. Breakfast included .The room is fully furnished with two single beds and... View all property information
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    Kissimmee, Central Florida 34746
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! Paradise Cay is the perfect place for your next vacation getaway. You'll be right at home in one of our spacious and comfortable townhomes, that offer all of the comforts of home at an affordable price. Book one, two or... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, Sleeps 8 | Quick View
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    Magnolia floor plan (2 floors) 3 bedroom 2.5 bath 1777sqft. This beautiful professionally decorated condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. The 4,000 square foot Oakwater clubhouse features a lagoon-style pool, tennis, volleyball and basketball... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    <h1 style='color: #76be43;'>Luxurious Orlando Vacation Home in Paradise Palms Resort, Kissimmee, Florida</h1><ul style='margin:0; padding:0; '><li style='margin:0; padding:0 0 0 15px; background-image:... View all property information
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    Kissimmee, Central Florida 34747
    1 / 16
    5 of 5 stars (13) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    located just off Hwy 192 and is within 3 miles to Disney. It is a gated resort with a large pool and sun terrace area, along with children's playground The home, located less than a minute's walk from the pool area, has 1 King master, 1 Queen room and one themed twin room. There are ceiling fans... View all property information
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    Kissimmee, Central Florida 34747
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This gorgeous Sunset Lakes villas is ideal for your next Orlando vacation. This villa has four spacious bedrooms and 3 baths and will comfortably sleep 8 guests. This 1770 plus square foot villa has a full kitchen and a lovely dining space as well as a comfortable living area. Relax all day or... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Dream villa is equipped with everything a family could need for a magical Florida vacation, while still enjoying all the comforts of home, including a washing machine, clothes dryer. A dining-room table and ample living room give families and groups plenty of space to spread out, relax and... View all property information
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    Kissimmee, Central Florida 34746
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    2317 sqft 5 bedroom 3 bath (2 story) Pool home. We invite you to enjoy your next vacation at our luxurious, brand new and beautifully decorated 5 bed/3 bath Home with 28ft pool. Sleeping accommodation features two elegant master suites with king size beds; one queen size; two twin bedrooms and 2... View all property information
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    Kissimmee, Central Florida 34747
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    7 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    This huge villa is located in the prestigious Emerald Island Resort. It has a total of 7 bedrooms and 6 bathrooms which makes it perfect for larger families travelling and sharing accommodations. The villa is nested in a nice quiet cul-de-sac and has a fenced in back garden for that extra privacy.... View all property information
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    Kissimmee, Central Florida
    1 / 39
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Windsor Palms Resort is conveniently just located just 3 miles form Disney. Just off Hwy 192 and within easy access of Interstate 4. Windsor Palms Resort has a 24 hour manned security gate house, and has unrivaled resort facilities that are freely available to all villa guests which include, 58... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 stars (9) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    This spacious second floor unit features 2 Bedrooms, 2 Baths, Living Room, Dining Room and a Brand New Kitchen. Ceramic tile throughout, new carpeting, new furniture throughout and Wi-FI High Speed Internet! Living Room has 27' Flat Panel TV with DVD Player, Master bedroom has queen-sized bed,... View all property information
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    Kissimmee, Central Florida 34746
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Child-friendly
    • x
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    • x
    About this property
    A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. The villa is spaciously arranged over two levels, making it ideal for one or two families The sitting room has... View all property information
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    Kissimmee, Central Florida 34746
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
    About this property
    Located 5 minutes away from Disney World, in the Regal Oaks Resort & Spa. Walk to Old Town with Fun Spot justt a walk away. Wander into one of the specialty shops or stop by one of the weekly Car Cruises that feature cars from many different decades. Then go next door to Fun Spot where you will... View all property information
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    Kissimmee, Central Florida 34746
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Welcome to Windsor Hills Resort and this stunning 5 bedroom, 5 bathroom rental home located near the theme parks in Orlando, with Florida. This vacation rental home has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense to dine... View all property information
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    Kissimmee, Central Florida
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complementary high speed wireless... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, Sleeps 10 | Quick View
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    Brighton floor plan - 1816 sq.ft. 4 bedroom 3 bath (1 story) South facing pool Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This home is absolutely perfect for large family groups. This property features all the... View all property information
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    Kissimmee, Central Florida 34747
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ********************************************************* Please click on Rates tab above or scroll down to see the rate section below for pricing. Westgate Vacation Villas Resort & Spa offers the finest in luxury accommodations just minutes from the main entrance to Walt Disney World® Resort and... View all property information
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    Kissimmee, Central Florida 34747
    1 / 33
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Apartment with 2 Bedrooms 2 Bathrooms with everything to make your stay in Florida a pleasant, master bedroom has a king size bed, the secondary bedroom has a Twin size bed and a bunk above and below Full Twin to comfortably accommodate 6 people the kitchen is fully equipped with cooker, fridge... View all property information
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    Kissimmee, Central Florida 34741
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    This beautiful 2 bed/2 Bath vacation apartment home comfortably sleeps 6 guests. 2 Bedroom with a balcony overlooking the lake view it is so relaxing and peaceful with contemporary decor, modern and updated furniture along with brand new appliances and a very spacious fully equipped kitchen. Your... View all property information
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    Kissimmee, Central Florida 34746
    9 Bedrooms, 10 Bathrooms, Sleeps 18 | Quick View
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    SIMPLY THE BEST NO QUESTION This is the largest rental home in Orlando Ignore what others state this is the house with a Combined area of over 14 000 sq ft Completed in 2012 to the most exacting standards If you want luxury this is the house Within reunion others make claims This is the largest... View all property information
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    Kissimmee, Central Florida 34747
    9 Bedrooms, 12 Bathrooms, Sleeps 18 | Quick View
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    Welcome to one of the most spectacular luxury mansions in Orlando This prestigious property enjoys a prime location in the fabulous Reunion Resort and presents 9 amazing bedrooms and unprecedented entertainment features Just 12 minutes from Walt Disney World your guests can enjoy the ultimate... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Situated on the first floor this middle unit luxury condo is in the tranquil setting of Sun Lake. Sun Lake Condos are located close to the well known Formosa Gardens. There has been no expense spared in making this a dream vacation home, furnished with all the new decor of 2013. This suberb... View all property information
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    Kissimmee, Central Florida 34747
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 Star luxury and comfort await you at our stunning brand new 3 bedroom Condo and is situated close to the amenities in Windsor Hills Resort There are 3 bedrooms and 2 full bathrooms All three bedrooms have TV s The home also has a CD radio player The living room has a sleeper sofa a TV and the... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    VIEW OUR CURRENT AVAILABILITY. ACCEPTING BOOKINGS FOR 2015 and 2016 NOW. 
Mickey's Ritz at Veranda Palms is a private vacation home providing spacious accommodation with luxury, upgraded contemporary furnishings. The home has 4 bedrooms, 3 bathrooms, a large pool + spa , a west facing pool deck... View all property information
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    Kissimmee, Central Florida 34746
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    Augusta floor plan 1206 sqft 2 bedroom 2 bath (1st floor unit) Welcome to this elegant, professionally decorated Orlando vacation condo, located in the beautiful Windsor Palms Resort. This property features all the comforts of home, and more! Windsor Palms is a gorgeous gated community, just... View all property information
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    Kissimmee, Central Florida 34747
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Completely refurbished, this is an immaculate 2 bed/2 bath all year holiday self-catering rental . Lake Marion Resort has it all. It is located on a 3800 acre fishing lake and is a quick trip away from restaurants and shops including a Supercenter Wal-Mart and Publix. The Clubhouse facilities... View all property information
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    Kissimmee, Central Florida 34759
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! Looking for a restful and comfortable stay? You have come to the right place! This 3 bedroom townhouse is located in the Crestwynd Bay resort, just 1.5 miles away from Disney. This gated community features a community pool,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The Villas at Seven Dwarfs Lane is the #1 and newest premier resort and vacation rentals in the Orlando area, near Disney World. Its proximity to Orlando's world-renowned attractions is unrivaled. Staying in one of Townhouse gives you automatic membership to all the private resort facilities, for... View all property information
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    Kissimmee, Central Florida 34746
    1 / 10
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    WHY STAY IN A HOTEL OR CONDO WHEN YOU CAN HAVE A WHOLE HOUSE ??? *** NEWS UPDATE*** OUR RESORT HAS BEEN REBUILT OVER THE PREVIOUS YEAR. WE ARE NOW PLEASED TO ANNOUNCE THAT OUR BRAND NEW CLUB HOUSE (GYM / COFFEE SHOP / BUSINESS CENTER ETC) AND BRAND NEW POOL ARE NOW OPEN !!! ADDITIONALLY WE ARE... View all property information
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    Kissimmee, Central Florida 34747
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Newly Renovated! 4 Bedrooms including: 2 Master bedrooms with King size beds and en suites 1 bedroom with Queen size bed 1 bedroom with double twin beds Games room with pool table and fos All rooms include cable programming with LCD TVs Screened Pool with Hot Tub and seating... View all property information
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    Kissimmee, Central Florida 34744
    1 / 25
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    About this property
    Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center. This 1500... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Windsor Hills Resort and this stunning 3 bedroom, 3 Bathroom rental (1416sq.ft.) located near the theme parks in Orlando, Florida.  This vacation rental has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense to dine in, with... View all property information
    Location Information
    Kissimmee, Central Florida 34747