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Holiday Rentals in Kissimmee, FL

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    ₹ 10,805 Average
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    Travellers to Kissimmee are booking March dates now. Secure your holiday home today, and have the perfect trip.
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Your family will be blown away by this gorgeous brand new 5 bedroom, 5 ½ bathroom villa. You are sure to not be disappointed with 2 game rooms, huge bedrooms and west facing private pool. You are guaranteed to be surrounded by luxury in the beautiful Reunion Resort. The focal point of your stay is... View all property information
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    Kissimmee, Central Florida
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Enjoy this spacious 4 bedroom 2 bath Orlando Florida-style vacation home situated in the tranquil estate of Windwood Cay. An attractive and quite location, Windwood Cay is well hidden from the busy surrounds of Kissimmee, but within easy walking distance of several restaurants and shops, including... View all property information
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    Kissimmee, Central Florida 34746
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    The Sanctuary is an impressive gated community of high quality homes set in beautifully landscaped communal areas. Redstone paving driveways and tree lined boulevards add elegance to the development. Champions Gate golf resort featuring two 18 hole courses designed by Greg Norman is a mere two... View all property information
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    Kissimmee, Central Florida 33896
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    The Bellavida Resort is located behind the famous Medieval Times Dinner Show and next to the Super Wallmart on 192 in Kissimmee. Minutes from all the amusement parks, Lake Buena vista, Premium Outlets, and the Orlando Int'l Airport. Surrounded by a vast conservation area, Bellavida has all the... View all property information
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    Kissimmee, Central Florida 34746
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    3 Bedroom 3 Bathroom Townhome with splash pool Nicely furnished and brightly colored, you will love this spacious end unit town home located in the ever popular Windsor Hills Resort community. There's close parking and the Clubhouse is within easy walking distance! This unit offers you comfortable... View all property information
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    Kissimmee, Central Florida 34747
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This renovated luxurious 6 bedroom, 4 bathroom villa is located on the 5 star premier gated and guarded resort community of Windsor Hills which only minutes away from the Disney theme parks. Windsor Hills is consistently voted the number one vacation home rental community in the Walt Disney World... View all property information
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    Kissimmee, Central Florida 34747
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    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... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ↵Property Reference #RVH_183 Centre Court Comfort - 3 Bed 3 Bath Condo Overlooking Golf Course Located in the upscale Reunion Resort community of Centre Court Ridge in Building E on the Third Floor Corner Unit has plenty of space for the whole family with lots of sunlight! This 3 bed 3 bath condo... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spacious 4bedrooms home, perfectly located in subdivision on Crescent Lakes. Rental is fully furnished and offers hardwood and ceramic floorings, Fully equipped kitchen,air condition, whole house sound system are part of modern amenities. Large and well maintained pool and lushly grounds makes... View all property information
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    Kissimmee, Central Florida 34758
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Built in 2014, our home has many modern conveniences to ensure a comfortable stay. The villa has also been professionally decorated to give an executive feel throughout. With two floors, four bedrooms, and three and a half baths, your party will be able to enjoy spending time together, but also... View all property information
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    Kissimmee, Central Florida 34746
    1 / 38
    5 of 5 bubbles (1) Excellent
    1 Bedroom, Sleeps 4 | Quick View
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    About this property
    Rated the number ONE accommodation in Kissimmee, Florida by Trip Advisor! Trip Advisor Certificate of Excellence Award three years in a row! One Bedroom Condo Third Floor King Size Master Bed Queen Size Sleeper Sofa Bed Sleeps up to 4 guests Fully Equipped Kitchen 4 Miles from Walt Disney World... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    HURRY!!! WEEKS STILL AVAILABLE FROM MAY 1 ONWARDS - SPECIAL RATE!! (please see current availabilities below) I am offering for rent our fully furnished 4 bedrooms 3 full bathrooms vacation house, 15 minutes away from all the major attractions like Downtown Disney, Disney World, SeaWorld, etc.... View all property information
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    Kissimmee, Central Florida 34758
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    INTERNAL CODE: AV4SPH5B12G The Property: This amazing 5 bedrooms vacation house is located in the city of Kissimmee, in the best touristic zone of the Greater Orlando, next to Walt Disney World, near to the Universal Studios theme parks and close to the Premium Outlets shopping malls. This... View all property information
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    Kissimmee, Central Florida 34746
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    4.5 of 5 bubbles (7) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Luxurious and well maintained Town home in with brand new furnishings. Beautifully furnished and elegantly decorated 2 Story townhome with Cable TV, Free Wi-Fi, and Free Unlimited Local and US calls. It gives you all the convenience and comfort a home can provide with full kitchen, large beds that... 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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    About this property
    This villa is a 4 Bedroom 3 Bathroom luxury vacation home, however there is a sofa bed in the sitting room so the villa can sleep 10 guests. The family room is luxuriously furnished and has wide-screen HD TV with premium cable and Bose sound system and patio doors leading out to a lovely deck and... View all property information
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    Kissimmee, Central Florida 34746
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    6 Bedrooms, 3 Bathrooms, Sleeps 15 | Quick View
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    Magnificent Orlando Florida vacation home situated on the exclusive guard gated estate of Windsor Hills, and is ideally located only five minutes from Walt Disney World. This luxurious home has 6 bedrooms, a large, screened South West facing pool terrace which sits on a plateau with fabulous views... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Larger families and groups of friends will love the Southampton vacation home in Kissimmee. This spacious 4-Star home features 4 bedrooms and 2 bathrooms, of which will comfortably sleep 10 guests. There is plenty of room to lounge in the two full living rooms. The Southampton is located close to... View all property information
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    Kissimmee, Central Florida 34746
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    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Welcome to this luxurious four bedroom vacation home located within the prestigious gated resort of Windsor Palms. Windsor Palms is one of the most sought after communities in Central Florida and offers an array of community facilities which are the envy of many other resorts. This property offers... 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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    Beautiful 2 story vacation luxury house. Master bedroom with king size bed, balcony and private bathroom. Second and third bedrooms with queen size beds. Two bedrooms with twin size beds (first floor with 1 bedroom with twin beds). Home computer with Internet/wifi service and all local/long... View all property information
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    Kissimmee, Central Florida 33896
    1 / 33
    5 of 5 bubbles (6) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a beautiful vacation rental home 5 minutes from Walt Disney World in Kissimmee, Florida. It has 4 bedrooms and 3 full bathrooms. This spacious villa sleeps 9 people in total comfort. The functional floorplan boasts a bright, open living area with separate dining area and kitchen. Our... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sunset Lakes is a semi-residential gated community situated off the 192 Irlo Bronson Highway approximately 2 miles west of Interstate 4. World Drive, which is the entrance to all the Disney theme parks is less than 10 minutes drive away. Universal Studios, Sea World and International Drive... 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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    You will love staying at this home in a beautiful setting! Sit back and relax on the covered porch and watch the ducks swim by. Sit in the hot tub and melt the stress away after a long theme park day. It has a screened-in private pool to float around in and swim some laps. An open concept fully... View all property information
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    Kissimmee, Central Florida 34746
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Only minutes from the entrance of Walt Disney World, this brand new ‘Glamorous’ 4 Bedroom 3.5 Bath End Unit Town Home located in Compass Bay is one of four beautiful town homes in the same building. This works perfectly for a small family vacation or a grand family gathering. This exquisitely and... View all property information
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    Kissimmee, Central Florida 34746
    1 / 26
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Chatham Park deluxe vacation villa is located on a private lakeside lot with a beautiful, year-round sunset view. Chatham Park offers 24/7 security for your peace of mind. This luxury vacation rental is exceptionally modern and features a private, screened-in heated pool. The location is... View all property information
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    Kissimmee, Central Florida 34746
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The Deluxe Villa sleeps up to six people comfortably with a king-sized bed in the master bedroom, two twin beds in the guest bedroom, a sofa in the living room that opens into a queen-sized bed, (plus a folding bed). With two full-sized bathrooms and approximately 1475 sq. ft. to spread out in, you... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 Townhome gives you automatic membership to all the private resort facilities, for... View all property information
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    Kissimmee, Central Florida 34746
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    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Very comfortable villa with loft, located on Westgate Vacation Villas Resort - Kissimmee, minutes away from all Orlando Theme parks. The villa has a king size bed, 2 double beds, 2 Twin Beds in the Loft and a Queen Sleeper Sofa in the living area. It also has a Fully Equipped Kitchen, dining area,... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    The villa has 4 bedrooms and 3 1/2 bathrooms, arranged to sleep 8 in comfort. The villa benefits from an oversized pie shaped plot with a south facing pool looking out to conservation woodland. The pool area, which is not overlooked, provides maximum daily exposure to the Florida sunshine but it... View all property information
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    Kissimmee, Central Florida 34746
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Westgate Town Center Resort & Spa provides guests all the comforts of a fully furnished home just 1 mile from Walt Disney World® Resort and minutes from other Orlando area attractions. With a variety of accommodation choices – ranging from cozy studios to oversized four-bedroom villas – along with... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Great familly vacation villa consisting of 4 bedrooms and 3 full baths located less than 3 miles from Disney in the Gated Community of Windsor Palms. Large southwest facing pool with no rear neighbors and sun all day.Two master suites with ensuites and 2 twin rooms with shared full bath. Infant and... View all property information
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    Kissimmee, Central Florida 34747
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    "Imagine Renting This Stunning Villa In One Of Orlando`s Most Prestigious Resorts, 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... View all property information
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    Kissimmee, Central Florida
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Property Ref: RVH_107 Situated in the highly sought after Liberty Bluff neighborhood of the Reunion Resort this luxurious 5 bedroom 5.5 bath sits atop of the signature Legacy course, and boasts panoramic views of the greens and The Main Grande. The Villa definitely lives up to it's name. The... View all property information
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    Kissimmee, Central Florida 34747
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    The finest in luxury accommodations just minutes from the main entrance to Walt Disney World® Resort and within close proximity to Universal Orlando® Resort and SeaWorld® Orlando<BR>Dining options include Sid's Bistro, Joe's Marketplace & Deli, Drafts Sports Bar & Grill, Hershey's Ice Cream Shop,... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 bubbles (1) Excellent
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    Spacious & Tastefully Furnished 5BR 4.5 BATH Villa -3 Master Suites, large deck, private pool & Spa, close to DISNEY This bright and spacious Villa is tastefully decorated and located conveniently close to Shopping, Dining and all major attractions. On the ground floor you will find the living... View all property information
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    Kissimmee, Central Florida 34746
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    Townhouse near Disney is located in the Regal Oaks at Old Town resort, a gated community directly behind Old Town Kissimmee, within 5 to 10 minutes walk of a variety of bars and restaurants. The resort offers an extensive pool area and sundecks, together with a clubhouse providing bars, a... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Just in the best place! Magic Villa View is situated in Linfield's Estate area. This luxury villa sleeps up 8 people and is beautifully furnished, fully air conditioned with its own screened and private pool area with a salt system just to care you and a magical view to the lake. The villa is fully... View all property information
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    Kissimmee, Central Florida 34747
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Our Deluxe Villas offer all the comforts of home, providing a fully equipped kitchen, full-size TV and DVD/CD in the living room and master bedroom, dining area, living room with queen sleeper sofa in most units, private balcony with chairs and access to a Washer/dryer. As the official on-site... View all property information
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    Kissimmee, Central Florida 32805
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Patio
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    • DVD Player
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Furnished as a luxury executive home, it is surround by a landscaped effect so it is not overlooked. South facing means the sun is captured for the greatest amount of time. There's nothing like returning from a day at the parks, to enjoy the pool with the last moments of the day's sun. The... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    Wonderful 6 beds, 3 ½ baths vacation home, approximately 3,282 square feet, with enclosed pool. The perfect place to relax after a long day at the parks. This beautiful pool home is located in the Cumbrian Lakes area of Kissimmee resort community located approx. 12 miles from Disney World. This... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
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    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    Newly renovated and fully furnished vacation town home in a gated community. It is conveniently located only two miles to Disney Parks, Downtown Disney, water Parks and also close to Sea World and Universal Studios. This luxury three bedroom three bathroom townhouse features a living room with... View all property information
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    Kissimmee, Central Florida 34747
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    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Townhouse is located in a gated community / Venetian Bay Villages.Our home is tastefully decorated. It can accommodate up to 8 people and includes luxury amenities such as master bedroom with two person jacuzzi tub.Upstairs is a Junior master bedroom with a Queen bed and full en -suite... View all property information
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    Kissimmee, Central Florida 34741
    1 / 58
    9 Bedrooms, 6 Bathrooms, Sleeps 24 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Grand Opening! This brand new, upscale, luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. It features 4369 sq. ft. living space and is... View all property information
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    Kissimmee, Central Florida
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    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Set 15 minutes from Walt Disney World® Resort, 24 minutes from SeaWorld Orlando and from Universal Orlando Resort, this beautifully designed and furnished 4,000 Sq.ft. 5 bed 5.5 bath villa with luxurious pool and third floor game room overlooking the fairway and green on the 6th hole of the... View all property information
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    Kissimmee, Central Florida 34747
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    "Picture This...You Renting a 5-Star Villa in Orlando`s Most Prestigous Resort, Windsor Hills, Only 1.5 Miles from the Gates of Disney" 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 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    • ?
    About this property
    Enjoy your luxury vacation staying only 10 minutes from Disney in a modern vacation home! - Gated community - Less than 5 minutes to the grocery store - Close to Universal and outlet shopping malls - Enjoy the complimentary access to the heated resort pool / playground / clubhouse / gym /... View all property information
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    Kissimmee, Central Florida 34746
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    Highlights; Conservation view Less than a 1 minute walk from the clubhouse and pool Flat screen TV's throughout home Free high speed Wi-Fi Gated resort style community Full size Washer / Dryer Description; A fully air conditioned 3 bedroom condo, with 2 bathrooms, this second floor unit is... View all property information
    Location Information
    Kissimmee, Central Florida 34747