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Holiday Rentals in Kissimmee, FL

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    Travellers to Kissimmee are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located within a few miles of Disney World and minutes away from Universal Studios, SeaWorld, and all major convention centers in the Orlando area. This Nest-Away™ studio is located in an exclusive gated resort with high-end hotel quality amenities featuring pools, fitness center, spa, sauna,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 52
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    “Imagine…. You and your Family Renting this Luxurious 7 bedroom Private Vacation Rental located on one of Orlando’s most prestigious resort, Reunion Resort overlooking Watson PGA golf course, only 6 miles from Disney" Villa W115 Gathering Ct, Reunion Resort, Orlando TYPE: VILLA | BEDS: 7 | BATHS:... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    3,000 square feet, the two-story, 6-bedroom residences feature a first-floor bedroom, multiple master suites, a gourmet kitchen, dining room, spacious great room, 5-½ baths and covered lanai. Florida-inspired architecture with open floor plans, a private in-ground pool, a two-car garage and plenty... View all property information
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    Kissimmee, Central Florida 34747
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    So close to Disney, actually within 10 minutes away and you can enjoy all the magic of Orlando in this fully furnished 2 br 2a condo. The grounds alone has enough to keep you home with pools, lake, walking trails, activity center and so much more! Your 2 bedroom condo sleeps 8. It has a king... View all property information
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    Kissimmee, Central Florida 34746
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    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Sunridge woods is a select quiet community situated on County Route 54, just 2 miles east of Interstate 4, approx. 10 minutes drive to Disney and the major Theme Parks, restaurants and ‘fast food’ outlets on the US-192. A Publix supermarket is open at Champions Gate, a large golf complex, only 3... View all property information
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    Kissimmee, Central Florida
    1 / 33
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    This fabulous 6 bedroom vacation home is the perfect place for you and your family to enjoy a stay to remember and cherish, when you come to visit the theme parks and attractions of Orlando. Located on the Bella Vida Resort - where you can have a magical vacation that your family will remember... View all property information
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    Kissimmee, Central Florida 34746
    1 / 32
    4 of 5 bubbles (5) Very good
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    At Reunion Retreat, relaxation is just the beginning of your Orlando vacation. Reunion Resort features a world of Orlando vacation resort amenities to accommodate your family or group. Whether it's you and the kids, a golf getaway, business event or a family or group get-together, Reunion Resort... View all property information
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    Kissimmee, Central Florida 34747
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    1 / 30
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    3 BEDROOM 2 BATH CONDO FOR RENT AT WINDSOR HILLS! Best Price GUARANTEE. CLOSEST TO DISNEY - BE ON PROPERTY IN TWO MINUTES. Full Use of ALL Windsor Hills Amenities -KING Master Bed -FREE Wireless Internet -Flat Screen HDTV and DVD Players EVERY ROOM -Electronic Door Locks (No... View all property information
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    Kissimmee, Central Florida 34747
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A Wonderful And Comfortable House Built In 2015, This Beautifully Decorated, Is Ideal To Receive For This Family. The House Has 4 Bedrooms, One Bedroom Downstairs With A Kingbed And A Bathroom. Upstairs Has 3 Bedrooms, A Master Suite With King Bed And Big Bathroom, A Bedroom With Two Twinbeds And... View all property information
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    Kissimmee, Central Florida 34747
    1 / 31
    Studio, 5 Bathrooms, Sleeps 1 | Quick View
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    About this property
    This Platinum Standard home is sure to fullfill all your dreams, situated in the prestigious "The Reserve at Windsor Hills Resort, at it´s best location" The villa is fully air conditioned with 5 bedrooms/5bathrooms and was decorated by an interior designer to a very high standard and has... View all property information
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    Kissimmee, Central Florida 34747
    1 / 21
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
    • Children's Pool
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    About this property
    NO EXTRA CHARGES FOR FAST WIFI, BABY EQUIPMENT, GRILL, LATE CHECK OUT where poss. FREE PHONE LOCAL & USA CALLS AND INTERNATIONAL TO LANDLINES. Stunning Lake side Villa near Disney on top gated and guarded resort. 7 Bedrooms 5 bathrooms with Private pool/24hr Spa/Gameroom/Lightening Wifi. 5 King... View all property information
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    Kissimmee, Central Florida 34746
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Lucaya 3 Bedroom 2 Bath Townhome! - Townhouse 3 Bedrooms / 2 Bathrooms. - Gated community. - Less than 5 minutes to grocery stores. - Accommodates up to 8 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 in... View all property information
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    Kissimmee, Central Florida 34746
    1 / 25
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    We are proud to offer this 6 bedroom, 6 bathroom vacation rental in the stunning resort community of Champions Gate. For those times, when dining in is the right choice, the kitchen, with its stainless steel appliances, granite counter tops and upgraded tile and cabinetry, has all the conveniences... View all property information
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    Kissimmee, Central Florida 33896
    1 / 45
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Characters Corner Vacation is a 6 bed/4bath Disney themed home located in the gated community of Formosa Gardens Estates, only 2 and 1/2 miles from Disney's main gate! Our family has owned & operated this vacation home since 2002 and we are constantly updating and improving! We love sharing our... View all property information
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    Kissimmee, Central Florida 34747
    1 / 71
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Another, superior, well appointed detached 3 bedroom villa, ideally situated on a small private development, a premium location, enjoying a relaxed, peaceful setting, and yet so close to the attraction pack See what a fabulous place you will be staying in. You'll be amazed at the standard on... View all property information
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    Kissimmee, Central Florida 34746
    1 / 21
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    ChampionsGate Resort is a stunning vacation home community, with a clubhouse that rivals any in the Orlando area. And, this gorgeous 6 bedroom, 6 bathroom pool home is sure to make your vacation special. Upon your arrival, you'll know that you are in for a great vacation. The tile roof and stone... View all property information
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    Kissimmee, Central Florida 33896
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a beautiful, spacious 3 bedroom 2 bathroom condo located in The Villas at Somerset . You may never want to go back home! Occupancy for this villa is limited to 6 people for the reason of comfort and safety. There is a living room where yourself and your guests will be able to kick back and... View all property information
    Location Information
    Kissimmee, Central Florida 34746
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    1 / 14
    2 of 5 bubbles (1) Poor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Harmony House is a luxury villa located in the prestigious Remington Golf Community and near Walt Disney World in Kissimmee, Florida. This upgraded executive Villa with extended Pool & Spa, has 4 bedrooms and 3.5 bathrooms and sleeps up to 8 guests in luxury. Remington golf course has won a Disney... View all property information
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    Kissimmee, Central Florida 34744
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
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    About this property
    This private 4 bedroom townhome is located at the beautiful Bella Vida Resort. Perfectly located for privacy, this townhome is perfect for those looking for peace and privacy. The townhome is a corner unit, with the private pool area facing a preserve. When you enter the home you feel at ease,... View all property information
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    Kissimmee, Central Florida 34746
    1 / 23
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • x
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    About this property
    This exquisite home will leave our guests with fond memories and a yearning to return as soon as possible! The new owner of the home done a fantastic job of refurbishing, styling and equipping this fantastic vacation home to the very highest standard with no expense spared! Since purchasing the... View all property information
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    Kissimmee, Central Florida
    1 / 7
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bed 3 Bath Pool Villa Additional amenities include: game room. View all property information
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    Kissimmee, Central Florida 34747
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This great 4 bedroom home is located in the sought after gated community Bella Vida Resort. Located in a cul de sac towards the back of the community, its perfect for families wanting a quiet, private home to relax and enjoy a simply perfect florida vacation. The home feels spacious and airy... View all property information
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    Kissimmee, Central Florida 34746
    1 / 35
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Our villa was completed in May 2006 & is situated on a large corner lot in the gated resort community of Windsor Hills. Enjoy the modern/contemporary look of this 6 bed 4 bath home with its clean lines and earth tones in every room. There are 2 king master en-suites, a third bedroom with a queen... View all property information
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    Kissimmee, Central Florida 34747
    1 / 25
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Your dream vacation awaits you with this luxurious 5 bedroom, 4.5-bathroom home. It is located in the resort community of Windsor at Westside, which is minutes from Walt Disney World. Leaving you in the heart of all the action and close to all the greatest attractions, shows, malls, shops and... View all property information
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    Kissimmee, Central Florida
    1 / 43
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    GRAND OPENING! Brand New Luxurious Waterfront Mansion YEAR 2013! Enjoy the grandeur in this resort-like sanctuary. Gourmet kitchen delightfully designed with custom cabinets and high-end stainless appliances. The Kitchen opens to a beautiful family room area leading out to the lakefront patio.... View all property information
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    Kissimmee, Central Florida
    1 / 29
    8 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Welcome to this beautiful 8 bedroom, 5 bathroom vacation home in the stunning resort community of Champions Gate. The fully equipped kitchen features stainless steel appliances, granite counter tops and upgraded tile and cabinetry. For your dining experiences, there is plenty of seating at both the... View all property information
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    Kissimmee, Central Florida 33896
    1 / 20
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. There are four bedrooms complete with full baths: two king master suites, a queen and a bedroom with twin beds. The chair in the nook makes into a single twin if necessary. Each bathroom has a... 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
    This fabulous vacation villa is a close drive to Walt Disney and is located in the community of Florida Pines. This home comes with 4 bedrooms and 2 bathrooms. Bedding configurations are a master suite with queen bed, one full and 2 sets of twins. Multiple TVs are available in this home for... View all property information
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    Kissimmee, Central Florida 33897
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Welcome to this stunning 5 bedroom, 4.5 bathroom vacation rental in beautiful Champions Gate. This home features a professional furniture package that includes leather furniture and 2 large flat screen TVs along with flat screens in each of the bedrooms and the game room. Speaking of game room, it... View all property information
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    Kissimmee, Central Florida 33896
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    About this property
    This large, brand new, exclusive villa of about 2681 sq.ft. contains 5 bedrooms (two masters) and 4.5 baths. You will really enjoy this open two storey floor plan! You have a nice pool view from the large corner kitchen with the barstools. You may watch the 50” SMART-TV (3D) with plenty of channels... View all property information
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    Kissimmee, Central Florida 33896
    1 / 22
    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 / 16
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Spacious Executive home in a 24 hour guard gated community. All the amenities for you to enjoy including Wi-Fi, Large Pool/Spa & Game Room. This 2 storey home has a Master Bedroom with ensuite on the first level, 2 additional Master Bedrooms with an ensuite and 3 Twin Bedrooms on the second floor.... View all property information
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    Kissimmee, Central Florida
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    About this property
    This is a family villa situated only 10 minutes from the Disney parks, but on a very quite gated community, overlooking a lake at the rear and a conservation area at the front. The villa has a covered swimming pool, 4. Bedrooms, 1 king, 1 queen and two twin, with three bathrooms, the kitchen is... 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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    About this property
    You'll feel the magic the moment you drive up to the exclusive Emerald Island gated community. You deserve the best, and we've provided it for you! Just unpack your bags and relax in your Five bedroom, three bath home away from home. Why be stuck in a small hotel room when you can stay in a... View all property information
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    Kissimmee, Central Florida
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    "Imagine Renting a 5-Star Florida Holiday Villa In Orlando`s Most Prestigious Resort, Reunion Resort. You'll love this luxurious villa with Private Pool" This villa is situated in the exclusive resort of Reunion, only 6 miles from Walt Disney World and all the major Orlando attractions. Great,... View all property information
    Location Information
    Kissimmee, Central Florida
    1 / 25
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • DVD Player
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    • Washer
    • Porch
    • Satellite TV
    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Only 4 miles to Disney World! 3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! Paradise Cay is a classy resort that meets the vacationing needs of couples, families or large groups with ease. You will rejoice in the convenience of this resort that is just minutes... View all property information
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    Kissimmee, Central Florida 34746
    1 / 27
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This six bedroom beautifully decorated home features an east facing pool and has all the comforts of a perfect vacation home for your enjoyment in Trafalgar Village Resort, which offers a unique Resort experience. Located about 15 minutes from the Disney theme park area, this is an ideal location... View all property information
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    Kissimmee, Central Florida
    1 / 24
    7 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful seven bedroom / six bathroom home is situated in the exclusive “Enclave” section of Emerald Island, a gated resort community which is within 5 minutes' drive of Disney World.<BR><BR>It is an ideal location for large family groups. Inside, the house is fully equipped to a very high... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    1 / 33
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
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    • Secure Parking
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    "THE LION KINGS!" Disney World area home! Just 5 to 7 minutes from Disney World and only 15-20 minutes from Universal and Sea World, this absolutely gorgeous home will give you and your family unforgettable memories. We have hundred's of 5-star "Rated Excellent! testimonials and emails from other... View all property information
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    Kissimmee, Central Florida 34746
    1 / 37
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This dazzling vacation home "Indulge in Luxury" is situated on the 4th hole of the Tom Watson golf course, with spectacular views from the sparkling private pool and spa. No expense was spared with this home, combining the luxury of old-world European design with top of the line modern electronics... View all property information
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    Kissimmee, Central Florida
    1 / 11
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax by your private pool with your favorite cocktail or join in at the fantastic resort pool and spa. For those with energy to spare, work out in the well equipped fitness center or have fun on the basketball and volleyball courts. This brand new, clean, well maintained and beautifully decorated... View all property information
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    Kissimmee, Central Florida
    1 / 47
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Washer
    • Balcony
    • DVD Player
    • Parking
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    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! Welcome to Sun Lake condo, just 1 of 3 identical units that we have available in this wonderful resort, is the perfect place for your next vacation getaway. This gorgeous condo meets the vacationing needs of couples,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Patio
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    • Satellite TV
    • Hot Tub
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    ******20% off discount on your rental rate if you stay anytime from now until end of November 2016****** This phenomenal Terra Verde Resort Town-Home has three bedrooms and two bathrooms. The Disney vacation rental sleeps up to 6 comfortably - the perfect place to vacation with family and friends!... View all property information
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    Kissimmee, Central Florida 34746
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Washer
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This Single-Family Home has 5 bedrooms, 3 baths, and approximately 3,000 square feet. Stay in this luxurious 5 bedroom and 3 bathrooms home with all the comforts for up to 14 people. The house is located at approximately 10 minutes from all of Disney World's featured theme parks and attractions.... View all property information
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    Kissimmee, Central Florida
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Warm weather and a beautiful environment make Florida a desirable vacation destination throughout the year. One of the most popular cities in The Sunshine State is Orlando, and to accommodate traveler demand, we invite you to stay at our deluxe condos at Villas at Somerset<BR><BR>Villa features a... View all property information
    Location Information
    Kissimmee, Central Florida 34746
    1 / 35
    4.5 of 5 bubbles (7) 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
    Our luxury townhouse was completed in October 2007 and is based at the brand new fully managed resort of Regal Oaks at Old Town Kissimmee.The property is only a short walk from Old Town with its many attractions including bars, restaurants, shops and fairground. There are many more restaurants &... View all property information
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    Kissimmee, Central Florida 34746
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Secure Parking
    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is a time share about 20 minutes from Disney It has a barbecue and about 4 pools and Walmart is in walking distance Calypso Cay Vacation Villas is a Premiere Time Share Resort located 7 miles away from Walt Disney World® Resort, Universal Studios Florida and SeaWorld Orlando. Our luxury... View all property information
    Location Information
    Kissimmee, Central Florida 34746