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Kissimmee Luxury Rentals

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    Travelers to Kissimmee are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1,020 Matching Rentals in KissimmeeView all 6,795 rentals
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    9 Bedrooms, 13 Bathrooms, Sleeps 22 Quick View
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    "Picture This.... You and Your Family Renting a 5-Star Luxury Mansion on Reunion Resort that Sleeps 30 People, Has an Extra Large Private Pool beside 2 PGA golf courses and Only 6 Miles from Disney" Villa W149 Twin Eagles Loop, Reunion Resort, Orlando TYPE: VILLA | BEDS: 11 | BATHS: 11.5 | POOL:...
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    Kissimmee, Central Florida 34747
    Rental Home - 11 Bedrooms, 12 Bathrooms, Sleeps 30
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    12 Bedrooms, 15 Bathrooms, Sleeps 26 Quick View
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    This stunning custom home is designed with an exclusive lifestyle in mind. This unique residence is the perfect place to spend your days or evenings at play or relaxing, occupying a prime location within the resort whilst offering privacy and seclusion. If curb appeal is what matters then this home...
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    Kissimmee, Central Florida 34747
    Rental Home - 12 Bedrooms, 15 Bathrooms, Sleeps 26
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    11 Bedrooms, 12 Bathrooms, Sleeps 30 Quick View
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    This dream home is situated on the Estates area of the Reunion Resort which boasts the largest home sites available. Designed and constructed by one of Reunion's leading custom builders, this 11 bedroom home boasting 14000 sq ft of living space has incorporated all the elements required to make a...
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    Kissimmee, Central Florida 34747
    Rental Home - 11 Bedrooms, 12 Bathrooms, Sleeps 30
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    10 Bedrooms, 11 Bathrooms, Sleeps 20 Quick View
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    "Imagine...You and Your Family Relaxing at This 5 Star Florida Holiday Villa on Reunion Resort, with a Private Pool, Spa, Gym and more and Only 12 Minutes from Disney World" TYPE: VILLA | BED: 10 | BATHROOM: 10.5 | SLEEP: 20 | POOL: YES | SPA: YES | GAME ROOM: YES | MOVIE THEATRE: YES This 11,453sq...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 11 Bathrooms, Sleeps 20
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    A luxury vacation, minutes from Disney World, Bush Gardens, Sea World and shopping galore, is within your grasp. Westgate Town Centre in Kissimmee, Florida is a luxury family resort that has it all and more. This is a two-bedroom lock off unit which gives you the option to holiday for one week in...
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    Kissimmee, Central Florida ON K0E
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    “Picture You and your Family Renting this Amazing Private Vacation Rental with pool, spa, secret teenage den, play room and movie theatre and more, located on one of Orlando’s most prestigious resort, Reunion Resort, only 6 miles from Disney" Villa W207 Palmilla Ct, Reunion Resort, Orlando, Florida...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 24
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    A magnificent 8 bedroom mansion that sets new standards for luxury accommodation on Reunion Resort! Located in a beautiful location alongside the challenging Jack Nicklaus designed PGA course, this stunning vacation rental property becomes a destination of its own for discerning travelers. With...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 24
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    9 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    Our dream builders will be back soon with further updates, including nightly rates, room layouts and availability! If you are looking for a dream vacation home and can't quite find what you want, just call or email us, we could have the perfect home in the making! This fabulous 9 bedroom layout is...
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    Kissimmee, Central Florida
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 22
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    8 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    About this property
    Overview Take a look at another dream vacation home that is now a reality in a beautiful location within Reunion Resort. If you are in search of a large, luxurious vacation rental home, we know that this property is going to create a lot of fun, excitement and unforgettable memories for our guests....
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    Kissimmee, Central Florida
    Condo/Apartment - 8 Bedrooms, 9 Bathrooms, Sleeps 20
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Hot Tub
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    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 9 Bedrooms 10.5 Bathroom 10000 sq ft Private swimming pool Private spa Private...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    11 Bedrooms, 10 Bathrooms, Sleeps 30 Quick View
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    “Imagine…. You and your Family Renting this Luxurious 11 bedroom Private Vacation Rental with pool, spa located on one of Orlando’s most prestigious resort, Reunion Resort only 6 miles from Disney" TYPE: VILLA | BED: 11 | BATHROOM: 10 | SLEEP: 30 | POOL: YES | SPA: YES | GAMES ROOM: YES | GYM: YES...
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    Kissimmee, Central Florida 34747
    Rental Home - 11 Bedrooms, 10 Bathrooms, Sleeps 30
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    8 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    "Imagine you and your family renting this Beautiful 8 bedroom Villa with private pool, spa, cinema theatre, games room with arcade games. And it's only 12 minutes from Disney!" Entertainment Features A highly specified games room with arcade games Tiered home theatre South east facing pool deck and...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 22
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    9 Bedrooms, 11 Bathrooms, Sleeps 20 Quick View
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    This home overlooks Reunion Resort’s signature Tom Watson golf course and comes complete with everything you need for a platinum-level getaway. With seven luxurious king suites and two unique kids rooms, everyone will feel like the star of the show! Each bedroom has a full en-suite bathroom, and...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 11 Bathrooms, Sleeps 20
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    8 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    About this property
    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: TV in every bedroom, paved parking, games/theater, privacy fence, reunion resort location, golf view, has spa, near disney - 12 mins, has pool, large luxury villa sleeps 22 (+2).
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    Kissimmee, Central Florida
    Condo/Apartment - 8 Bedrooms, 10 Bathrooms, Sleeps 22
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    Huge New Luxury Theme Vacation Home by Disney1 / 38
    (1)Excellent
    9 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    9-Bedroom, 9.5-Bathroom, Sleeps 22 Guests, Signature Estate Vacation Home in Reunion Golf Resort with Private Pool&Spa, Game Room&Home Theater. Brand new family friendly vacation home with Luxury Furnishing and access to Reunion Championship Course. Experience luxurious resort-like amenities in...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 22
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    9 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    About this property
    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: foosball, games, game room, children's themed bedrooms- minions, toy story, star wars themed home theater and games room, TV in every bedroom, paved parking, private pool deck and spa, privacy fence, 9...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 9 Bedrooms, 10 Bathrooms, Sleeps 20
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    8 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    “Picture You and Your Family Renting this Beautiful 8 bedroom Vacation Rental with private pool and spa, located on the prestigious Reunion Resort, located 10 minutes from Disney World" New home finished 2016 Set in a prime location in the most beautiful area of Reunion Resort, this stunning 8...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 20
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    8 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    About this property
    8 bedrooms in total (all with bathrooms) - 3 ground floor - 5 upper floor Two themed kids rooms Movie room Game room Small office Laundry room Full ensuite in each bedroom State of the art kitchen, dining room, great room Basketball court in garage Covered balcony and covered patio for grilling,...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 20
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    7 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    “Imagine You and your Family Renting this Amazing Vacation Rental with pool, gym, mine craft themed games room & more, located on one of Orlando’s most prestigious resort, Reunion Resort" Villa W231 Reunion Resort, Orlando, Florida TYPE: VILLA | BED: 7 | BATHROOM: 7.5 | SLEEP: 18 | POOL: YES | SPA:...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 18
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    7 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    “Imagine…. You and your Family Renting this Luxurious 7 bedroom Private Vacation Rental with pool & spa, located on one of the closest resorts to Disney, Formosa Gardens, less than 10 minutes from Disney" Located in the exclusive community of Formosa Gardens Estates this sumptuous, super estate...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 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...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    Three stories of luxury living are yours to enjoy in this newly renovated estate home in Legend's Corner overlooking the 10th tee and future clubhouse of the Signature Jack Nicklaus Tradition Course.  With over 5,600 square feet of living space, everyone can spread out and enjoy all that this...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    About this property
    This previous model home has everything you could imagine and much, much more.  With high end finishes, furnishing, appliances and amenities galore, there is surely something for everyone in your party to enjoy.  The home has four bedrooms in the main house with a separate guest suite housing the...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    About this property
    Welcome to Valhalla at Reunion Resort, a world-class resort home. This home is ultra luxurious inside and out. The open floor plan is exquisitely decorated and includes a stunning leather furniture package. The great room features a huge 70-inch flat-screen TV, with Blu Ray player. For dining,...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 20
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    “Imagine…. You and your Family Renting this Luxurious 4 bedroom Private Vacation Rental with pool & spa and beautiful views, located on Reunion Resort, 10 minutes from Disney" A new, modern and very stylish 4 bedroom luxury vacation home that's close to all of the amazing theme parks,of Central...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    King Palmilla1 / 49
    (1)Excellent
    8 Bedrooms, 11 Bathrooms, Sleeps 18 Quick View
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    Reviewed December 27, 2016
    We booked this beautiful home for our Christmas vacation to Orlando. I'll just say that the pictures don't do it justice. It's even more beautiful in person. This wasn't our...
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    About this property
    This amazing luxury villa rental is located in Orlando's Resort Reunion Resort. Featuring 9,145 sq.ft of living area under roof, 8 bedrooms all with en-suite bathrooms, games room, gymnasium, amazing cinema room, private pool, spa, pool water slide and summer kitchen plus the most amazing...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 11 Bathrooms, Sleeps 18
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    7 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    Newly built in 2015, this magnificent 7 bedroom luxury home offers the ultimate vacation retreat in the Disney Parks area of Central Florida. With 2 ground floor bedrooms, one of which is wheelchair accessible, plus 5 further bedrooms on the upper floor, your whole family and friends can join you...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 18
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    A new, modern and very stylish 4 bedroom luxury vacation home that's close to all of the amazing theme parks,of Central Florida! If you are looking for a very special upscale vacation rental home in the Kissimmee area, you have found the perfect dream home, set with stunning golf views in the...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    11 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Now available for 3 night stays or more!Key features 11 Bedrooms 10.5 Bathrooms Sleeps 22...
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    Kissimmee, Central Florida 34747
    Rental Home - 11 Bedrooms, 10 Bathrooms, Sleeps 22
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    "This Luxury Vacation Rental is perfect for You and Your Family. This 5 Star 3 Storey Vacation Home has 5 bedrooms including a private pool, spa, games room and so much more, It’s only 6 miles from Disney" Villa W163 Muirfield Loop, Reunion Resort, Orlando, Florida TYPE: VILLA | BEDS: 5 | BATHS: 5...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    11 Bedrooms, 11 Bathrooms, Sleeps 22 Quick View
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    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: game room, games, video game library, in-home theater, private pool deck with spa, TV in every bedroom, paved parking, privacy fence, upstairs loft with games area, 11 bedrooms, sleeping up to 22 people, has...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 11 Bedrooms, 11 Bathrooms, Sleeps 22
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    Spectalular Custom Home at Formosa Gardens1 / 40
    (1)Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Reviewed April 16, 2017
    Very close to the Disney parks, Braves spring training, I-4, shopping, groceries, etc.One of the largest pools you can get, it had something for our adult family...
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    About this property
    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: foosball, games, video game library, game room, the pinnacle of luxury vacation living, over 8000 sq ft of air conditioned space, incredible lagoon style pool, cd player, packn play, crib, 7 guest suites with...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    About this property
    The ultimate 5 bedroom luxury home with an incredible theme in every room! If you love the idea of a real escape from every day life, this spectacular home offers a little touch of magic from the world's greatest settings! There's even a room that is literally 'Out Of This World!' No expense has...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    9 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    Smoking allowed
    About this property
    "This Luxury Vacation Rental is perfect for You and Your Family. This 5 Star Vacation Home has 9 bedrooms including, private pool, spa and a cinema, located less than 10 minutes from Disney" This luxury 2-story villa stands in a premier location in the exclusive and gated community of Formosa...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 20
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    "Imagine you and your family renting this Stunning 10 Bedroom Villa, located at the Encore Club at Reunion Resort with private pool, games room and more. Less than 10 minutes from Disney World" Villa EC056 Encore Club at Reunion Resort, Orlando, Florida TYPE: VILLA | BED: 10 | BATHROOM: 10 | SLEEP:...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    "Imagine you and your family renting this Beautiful 10 Bedroom Villa, located on the Encore Club at Reunion Resort with private pool & spa, games room and more. Less than 10 minutes from Disney World" Villa EC036 Encore Club at Reunion Resort, Orlando, Florida TYPE: VILLA | BED: 10 | BATHROOM: 10 |...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    About this property
    “Picture You and Your Family Renting this Beautiful 10 bedroom Vacation Rental located on the prestigious Encore Club at Reunion, located less than 10 minutes from Disney World" With a private pool, spa, games area and a choice of living spaces and bedrooms on two floors, this luxury vacation...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    About this property
    “Picture You and Your Family Renting this Beautiful 10 bedroom Vacation Rental located on the prestigious Encore Club at Reunion, located less than 10 minutes from Disney World" Enjoy waking up to a sun drenched pool deck and lanai at the Encore Club at Reunion during your next Orlando vacation!...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    10 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    About this property
    “Imagine…. You and your Family Renting this Luxurious 10 bedroom Private Vacation Rental with pool & spa and themed kids bedrooms, located on one of Orlando’s most prestigious resort only 10 minutes from Disney" Choose Your Encore Club at Reunion Special Launch Offer With a 20% Discount Plus a...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 20
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    About this property
    “Imagine…. You and your Family Renting this Luxurious 10 bedroom Private Vacation Rental with pool & spa, Sleeps 22, located on one of Orlando’s most prestigious resort, The Encore Club at Reunion, less than 10 minutes from Disney" With a much sought after west facing pool deck, this amazing luxury...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    Villa EC021 "Stunning 10 Bedroom Villa"1 / 33
    (1)Excellent
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    Reviewed March 6, 2017
    This is a very well appointed vacation villa for any large group gathering. We were a family reunion of 15, and the villa met our every need. It is very well furnished, with...
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    About this property
    "This Luxury Vacation Rental is perfect for You and Your Family. This 5 Star Vacation Home has 10 bedrooms including, private pool, spa and more, located 10 minutes from Disney" The Encore Club at Reunion offers an excellent choice of luxury vacation rental homes for guests to relax and enjoy a...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    “Picture you and your friends renting this luxury 10 bedroom villa for the perfect golfing holiday, with private pool & spa and entertainment area at The Encore Club at Reunion, close to Disney and many PGA golf courses" Take a luxury vacation near Walt Disney World and stay in this large family...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    Smoking allowed
    About this property
    “Picture You and Your Family Renting this Beautiful 10 bedroom Vacation Rental located on the prestigious Encore Club at Reunion, located 10 minutes from Disney World" An amazing opportunity to take the entire family to Orlando while staying in the most luxurious and spacious family reunion...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    About this property
    “Picture you and your family renting this luxury 10 bedroom villa with private pool & spa and entertainment area at The Encore Club at Reunion, located less than 10 minutes from Disney" A spacious luxury pool home near Disney! Set within Orlando's newest upscale family friendly vacation rental...
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    Kissimmee, Central Florida 34747
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    1 Bedroom, 1 Bathroom, Sleeps 22 Quick View
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    About this property
    This luxurious two-story house with 11 bedrooms, 10 full baths, and 3 half baths is a perfect place to call home while on your Orlando vacation. It offers a gourmet kitchen, fully equipped with all of the utensils, dishes, cookware, and appliances you should need during your stay. The eating area...
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    Kissimmee, Central Florida 34747
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 22
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    9 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Official Reunion Resort Home - Full Use of Amenities Complimentary, unlimited water park entry...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 20
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Imagine You and Your family renting this Luxurious Private Vacation Rental over looking a golf course, with a Private Pool, a Games Room & so much more, located on Reunion Resort in Orlando, only 6 miles from Disney World" This superb villa has an elevated position which overlooks the Jack...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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