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Kissimmee Vacation Rentals

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    Travellers to Kissimmee are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    3 Bedrooms, Sleeps 6Quick View
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    4 Bedrooms, Sleeps 10Quick View
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    8 Bedrooms, Sleeps 20Quick View
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    About this property
    Our Splended 3-bedroom, 2-bathroom vacation home is in the heart of Kissimmee. on a small development of only 144 Homes, called 'Windward Cay', it is known as the 'Jewel of Kissimmee' in a perfect location This really is a perfect vacation home for your family to enjoy a wonderful holiday in the...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    This four plus bedroom, three bath townhouse in an upscale gated resort community, has been TOTALLY RENOVATED! It has its own heated pool and is backed up to a wooded conservation area for privacy and yet just 2 min. walk to the clubhouse. Fully equipped and professionally decorated, this nice...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Sauna
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    SKC Villa is only 4.7 miles from Disney's MainGate<BR>Luxury Vacation villa rental, in Orlando, Florida<BR><BR>Set in a Gated Community<BR><BR>This 2 story Villa has, 4 bedrooms, 3 bathrooms, air conditioning <BR>and is set in a private location with its own private pool, spa and excellent games...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    • Shared Outdoor Pool (Unheated)
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    Welcome to this elegant, professionally decorated Orlando vacation pool home 1816 sq. ft. This home is absolutely perfect for large family groups. The home has 1 king suite, 1 queen suite and 2 bedrooms with 2 twin beds in each. This property features all the comforts of home, and more! TV''s in...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    FREE cancellation up to 32 days before check in(*). No security deposit required at check in(*) Our second story condo can accommodate your entire family and comes completely furnished with everything you could possibly need to make your stay enjoyable. Our kitchen is fully furnished for you to...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    This amazing 6 bedroom 6 bath vacation home rental is perfect for group of 12! This home consist of 3 Kings, 1 Queen, and 4 single beds, beautiful up to date modern decor, amazing vacation home rental by owner you do not want to miss! Located in Reunion Resort perfect dream vacation location for...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Solar-Power/Carbon Zero! Amazing 6 Bedroom Pool Home just 3 Miles from Disney Just installed: All new modern Solar-Power PV panels and efficient cooling systems give this home a super low carbon footprint! Our wonderful, 5-star pool home is fully refurbished and conveniently located in Kissimmee's...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    HOUSE SPECIFICATIONS Beds – 4 Baths – 4 Sleeps – 8 (rental rollaway beds are available to sleep up to 10) Private Pool and Spa Game room Fully equipped kitchen. 5 minute drive to Walt Disney World! Activities to do at Windsor Hills Resort: Billiards Room Tennis and Basketball Courts Putting Green...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    • Air Conditioning
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    Welcome to this elegant and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. The home boasts views for miles as there's no rear neighbors. You can even see the nightly fireworks at Disney World. Absolutely perfect for large family groups, this...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 10Quick View
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    West Lucaya 4 Bedroom 3 Bath Townhome! - Townhouse 4 Bedrooms / 3 Baths. - Gated community. - Less than 5 minutes to grocery stores. - Accommodates up to 10 people comfortably. - Free Wi-Fi. - Electronic lock. You do not need to get the physical key to open the door, just use the code provided on...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    Ideal Location!! 4 BR Resort Villa near Disney, pool, forest and so much more! Welcome! Come and stay in our gorgeous secluded resort townhouse, a corner unit nestled along a natural Florida conservation forest yet less than a 30 second walk to full clubhouse facilities. Less than a 10 minute drive...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Review
    3 Bedrooms, Sleeps 7Quick View
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    • Air Conditioning
    • Terrace
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    Beautiful 3BR 2.5BATH Townhome in amazing Vacation Resort "EMERALD ISLAND" Your Home away from Home. Fully equipped for family living! For the kids - unit has a pack 'n play, stroller and baby bath. The 3 bed rooms are as follows: 1 MASTER QUEEN bed room with TV, ceiling fans and balcony - private...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, Sleeps 6Quick 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 is...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 10Quick View
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    A great getaway home... Cozy fully furnished home with a bright kitchen and has lots of sunlight throughout the home...  Feel right at home in this spacious 4 bedroom 2 bath home. It has a sparkling pool and spa to jump into after a long day walking around theme parks and shopping. Enjoy your meals...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    THE GREAT FLORIDA ESCAPE! This exciting, ground floor Disney World area home has everything you could possibly want for your family Disney World or winter vacation. Your gated resort is in the upscale highly sought after Lindfields area of Kissimmee and is a 5-star vacation in of itself! And...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    Indian Creek- Kissimmee, Florida is an upscale community located just 5 miles from Walt Disney World. This resort community sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. During your stay you will enjoy this well appointed...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    Beautiful Penthouse 3 bed 2 bath Condo, Sleeps 8 and very Kid friendly You will really enjoy this 3 bedroom 2 bath penthouse , 4th floor condo (the largest condo available in Windsor Hills resort) with a great view located in the highly desirable resort of Windsor Hills. The community is...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    This beautiful villa features three bedrooms, two bathrooms and a private pool with spa. Recently furnished and decorated you will feel right at home. Once inside you will find a fully equipped eat-in kitchen to the left. Directly in front of you you will find the large and open living/dining room...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    THE NEIGHBORHOOD This home is within easy access to the big 3 major attractions: • Disney World • SeaWorld Orlando • Universal GOLF COURSES • Falcon's Fire Golf Course 3200 Seralago Boulevard, Kissimmee, FL 34746 • Celebration Golf Club 701 Golfpark Drive, Kissimmee, FL 34747 • Waldorf Astoria Golf...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick View
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    • Waterfront
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    This spectacular property sleeps 12 people in comfort, with 1 King Master, 2 Double, 2 Twin bedrooms and a sofa bed in the lounge. <BR><BR>Our luxurious Lakeside Villa is south facing, so our guests will enjoy a Pool Deck bathed in the wonderful Florida sunshine all day. It has the added benefit of...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Downtown Kissimmee
    5 Bedrooms, Sleeps 12Quick View
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    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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    Kissimmee, Central Florida 34741
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Welcome to this beautifully decorated condo in Bella Piazza! Plenty of seating for all guests. Beside the open kitchen there is a dining area for up to 4 persons plus additional 2 seats at the breakfast counter. The family room has a beautiful comfortable sectional sofa to cozy up and watch TV or...
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    Kissimmee, Central Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    This beautiful 4 bedroom home is new, has 2 suites and a private pool. It is ideally located close to US192 with many shops and restaurants, 10 minutes away from Disney and only 20 minutes from Sea World and Universal Studios. It is also conveniently located near SuperTarget, Walmart and much more....
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    This two story 4 bedroom 3.5 bathroom townhome is located in Regal Oaks: the perfect location for your next Orlando getaway. Situated right behind Old Town with Fun Spot right next door, entertainment abounds. Take a stroll down the brick lined street of Old Town and wander into one of the...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11Quick View
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    After a long day’s walk (or run – thanks, kids!) through Disney, there’s nothing quite like sinking into the warm, inviting bubbles of your very own, very spa. After a theme park marathon, there’s nothing quite like taking a day off for a family pool party, a foosball competition, or a movie...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    4 Bedrooms, Sleeps 8Quick View
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    This two story four bedroom three bathroom townhome is located in Regal Oaks: the perfect location for your next Orlando getaway. Situated right behind Old Town with Fun Spot right next door, entertainment abounds. Take a stroll down the brick lined street of Old Town and wander into one of the...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    Amazing House at Windsor Hills 3 Bedroom 3 Bathroom Private Pool Free Wifi Free Cable Our exceptional Florida holiday home is located just a few minutes from Disney World. It combines the peace and tranquility of a protected wetland and conservation area while remaining central to the amazing...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    FREE cancellation up to 32 days before check in(*). No security deposit required at check in(*) This beautiful 3 bedroom/ 2 bath condo is located located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts, basketball courts, and attraction...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Downtown Kissimmee
    4 Bedrooms, Sleeps 8Quick View
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    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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    Kissimmee, Central Florida 34741
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    FREE cancellation up to 32 days before check in(*). No security deposit required at check in(*) Second floor unit - This beautiful 2 bedroom/ 2 bath condo is located 1.5 miles from Disney. (*) You can cancel your trip up to 32 days before check in and receive full refund minus the Damage and...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 8Quick View
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    Hello and Thank you for considering our Orlando Vacation Home. Our 3 bedroom, 2 bathroom, 1455 sq. ft. 2nd floor Condo sleeps 8 comfortably. There are 4 flat screen TV''s including a 50'' in the Living Room and a 32'' in the Master bedroom. There is a full size washer and dryer for your...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Reviews
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    At Minnie's Escape at Windsor Palms, you'll be provided with a wealth of features that will ensure that your next Florida vacation is a memorable one. Our Home Includes: Four spacious, elegantly furnished bedrooms - sleep in comfort. A private, heated swimming pool, perfect place for fun in...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    3 bed/2 bath condo, with elevator access, located on the 2nd floor of building #4 within the fantastic Windsor Hills Resort! Come and enjoy Florida living within a Tropical Tommy Bahama style condo. This luxurious 1,247 sq. ft corner unit has been furnished with an amazing upgraded furniture...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Villas at Somerset are centrally located to all the area attractions and restaurants and only minutes from Walt Disney World, Universal Orlando, SeaWorld and many other area attractions including the world class golf courses. This ground floor 3 bedroom condo with FREE Wi-Fi, has great...
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    Kissimmee, Central Florida 34746
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautifully decorated 3 bedroom 2 bat. These vacation townhomes can accommodate up to 8 guests comfortably. The home has all the amenities and commodities that you could possibly need to enjoy your dream vacation! • On the first floor, bedroom 1 (master), has a king size bed and a private bath • On...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    • Shared Outdoor Pool (Unheated)
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    Enjoy this beautifully spacious 4 bedroom and 3 bathroom Townhouse at the gated resort of Seven Dwarfs is the perfect get-away for your next vacation! This is a great home for a large family group since it can accommodate up to 12 if you include the sofa bed. This home is completely equipped with...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 10Quick View
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    • Children's Pool
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a really spacious loft villa that feature a king-size bed in the master bedroom with private bathroom and jetted tub, two double beds in the second bedroom, second bathroom with shower/tub combination, two twin beds in the loft, queen sleeper sofa in the separate living area with dining...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 14Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Located just 3 miles from the gates of Walt Disney, this fully air conditioned home away from home offers comfort and style throughout. To make your stay an extra special one, spread out, relax and enjoy a great night`s sleep! High speed internet access and telephone (free to call US and Canada)...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 9Quick View
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    • Satellite TV
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    Pet friendly
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    Our spacious 2 bedroom Villa includes all comfort of a home combined with the extra touches found at a great hotel. This villa features cable TV, Wireless internet, fully equipped kitchen with an oven, stove, dishwasher, refrigerator and microwave. Laundry and ironing facilities are also included....
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    6 Bedrooms, Sleeps 16Quick View
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    6 Bedrooms, 5 Bathrooms, Welcome to the SINGLE FAMILY HOME of your dreams in Kissimmee!! This 6 bedroom and 5 bathroom rental home located in the Storey Lake Resort Community. The 6 bedrooms and 2 living rooms, all together with 8 LED TVs. The large kitchen is a chef’s dream to cook in, with...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    3 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
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    • Patio
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    Pet friendly
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    About this property
    FREE cancellation up to 32 days before check in(*). No security deposit required at check in(*) Second floor unit - This beautiful 3 bedroom/ 2 bath condo is located 1.5 miles from Disney. (*) You can cancel your trip up to 32 days before check in and receive full refund minus the Damage and...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 14Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
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    GREAT LOCATION, BRAND NEW UNIT, 2 MASTER SUITES, FREE WIFI!! Located in the heart of Kissimmee, families of Storey Lake can easily access all Central Florida has to offer, including Walt Disney World, Universal Orlando, SeaWorld Orlando, and much more! 4703 Sleepy Hollow Dr Kissimmee, FL 34746 -...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 8Quick View
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    This stunning well-designed single storey pool house at the Seasons resort in Florida is a real gem. This quaint vacation home hidden amongst the tropical palms and fronds will delight you all around from its chic and simple exterior design to the modern and minimalistic touches inside. With a...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • DVD Player
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    Whether you’re seeking a world-class golf retreat or a visit to Disney’s “Most Magical Place on Earth,” this four-bedroom, three-bath townhome for 8 guests is the perfect base to discover Orlando-area attractions. The open-concept kitchen, living, and dining space leads out to a screened-in patio...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Vacation Home is a 3 BEDROOM TOWNHOUSE w/ FREE WIFI located at Seven Dwarfs Resort, a gated Resort community in Kissimmee, Florida. Just minutes away from the Disney Parks, Universal Studios, Sea World and other atractions. This 3 bedroom/2 bath townhome is fully furnished for your...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 9Quick View
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    • Washer
    • Satellite TV
    • Parking
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our spacious 2 bedroom Villa includes all comfort of a home combined with the extra touches found at a great hotel. This villa features cable TV, Wireless internet, fully equipped kitchen with an oven, stove, dishwasher, refrigerator and microwave. Laundry and ironing facilities are also included....
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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