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Holiday Rentals in Kissimmee, FL

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    Travellers to Kissimmee are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 39
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (31) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated and Affordable 3 bedroom 2.5 Bathroom Townhouse with Private Pool, Minutes to Disney, Restaurants and Shopping Newly renovated 3 Bedroom 2.5 Bath with Private Pool. This beautiful new and tastefully appointed townhouse is close to the 9000 sqft club house which features 2 large... View all property information
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    Kissimmee, Central Florida 34747
    1 / 31
    5 of 5 stars (8) Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Welcome to Orlando Disney top-class villa, the luxury, bright and spacious vacation home that has near 3000 sq/ft, 8 beds and 4.5 baths, located in the prestigious Emerald Island resort, Orlando, Florida. The villa can accommodate up to 4 families. It provides all of the benefits of your own home... View all property information
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    Kissimmee, Central Florida 34747
    1 / 14
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 BR private pool home close to Disney! Beautiful neighborhood, Free WIFI and Long Distance to US and Canada Montego Bay is a lovely, secluded neighborhoodnot not far off HWY192 and in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that Orlando has to... View all property information
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    Kissimmee, Central Florida 34746
    1 / 26
    4.5 of 5 stars (2) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Kissimmee, Central Florida 34746
    1 / 54
    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    We have the ideal location for a holiday close to the fabulous Central Florida attractions - including Walt Disney World, Universal and Sea World. With 4 bedrooms and plenty of space, the Indian Ridge Villa is ideal for small families, large families or two families sharing - for 2 to 8... View all property information
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    Kissimmee, Central Florida 34747
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    PLEASE VISIT THE LINK BELOW FOR ADDITIONAL RESORT INFORMATION AND REVIEWS FROM PRIOR GUESTS. STANDARD RATE: $660.00 PLUS $80.00 CLEANING FEE. TOTAL COST $740.00. POOL HEAT INCLUDED. PLUS FLORIDA TOURIST TAX (13%). OUR 4 BEDROOM VILLA IS LOCATED AT THE BEAUTIFUL 'BELLAVIDA RESORT' KISSIMMEE,... View all property information
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    Kissimmee, Central Florida 34746
    1 / 19
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Rolling Hills at Formosa Gardens villa description This magnificent and tastefully furnished villa is located in Rolling Hills Estates at Formosa Gardens, a prestigious community just three minutes away from Walt Disney World. Highway 192 famous for numerous restaurants, shopping and... View all property information
    Location Information
    Kissimmee, Central Florida
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    1 / 32
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located on the Regal Palms resort in Davenport this is a pretty end of terrace 2 story town home with 4 bedrooms and 3.5 bathrooms. As you enter there is a master bedroom with full size bed, double closet and en-suite bathroom with bath/shower, single basin and WC. This room has direct entry from... View all property information
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    Kissimmee, Central Florida
    1 / 15
    4 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This stunning remodeled 3 bedroom pool home has stunning lake and conservation views and is located in the heart of Kissimmee on the Creekside community. The master bedroom with king bed has en-suite and access to the pool area. All of the bedrooms have Flat screen Tv's one with a queen bed the... View all property information
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    Kissimmee, Central Florida 34746
    1 / 25
    3.5 of 5 stars (6) Average
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Trafalgar Villa is perfect for families and groups looking for fun, space, relaxation and sunshine. This luxurious home is located in Trafalgar Village Resort, a premiere resort community located just minutes from shopping, dining, and Disney! This house has 6 bedrooms with 5 bathrooms and is... View all property information
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    Kissimmee, Central Florida 34758
    1 / 59
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
    • Balcony
    • Patio
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    About this property
    Find Kissimmee Vacation Rentals on FlipKeyThis fantastic townhouse is an ideal home-away-from-home for your next vacation! Located in the Regal Oak resort just behind Old Town and “Fun Spot” USA off Hwy 192 and I-4, this vacation house is a perfect place to relax and unwind. The resort is situated... View all property information
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    Kissimmee, Central Florida 34746
    1 / 16
    4 of 5 stars (6) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    When you're not at Hogwartz, you should be here! This 4 bedroom home is a dream come true for Harry Potter fans everywhere! You won't need a magic wand to work on your tan while you're staying here! This home has a south facing pool, which means the most sun exposure all day! Additional... View all property information
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    Kissimmee, Central Florida 34747
    1 / 30
    3.5 of 5 stars (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    HI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLS Welcome to our family Florida Villa a Beautiful 4 bedroom 3 bathroom Vacation Villa Located in Orlando's most luxurious 24/7 manned gated community, Emerald Island Resort!! This luxurious home includes a Private... View all property information
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    Kissimmee, Central Florida
    1 / 51
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    <h1 style="color: #76be43;">Luxurious Orlando Vacation Home in Paradise Palms Resort , Kissimmee, Florida</h1><ul style="margin:0; padding:0; "><li style="margin:0; padding:0 0 0 15px; background-image:... View all property information
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    Kissimmee, Central Florida FL 34747
    1 / 29
    7 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    "At Last...You and Your Family Can Rent a 5-Star Florida Holiday Villa at Terra Verde, with a Private Pool, Superb Resort Facilities and Only 15 Minutes from Disney World" Superb luxury detached villa (sleeps 14) with private pool and spa. Set in an exclusive gated community, with a superb fishing... View all property information
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    Kissimmee, Central Florida
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Come enjoy your vacation in this brand new 4 Bedroom 3 Bath townhome located in the Festival Community, one of Orlando's newest and most exciting Resorts! This home is conveniently located to the attraction areas, shopping, restaurants and more. However, you may never want to leave the fun you can... View all property information
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    Kissimmee, Central Florida
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    We proudly present our Executive Villa located at the “Lake Berkley USA” Kissimmee, Florida. All on one floor. Convenient for guests with disabilities, elderly guests and guests with young children. Our Villa has been fully furnished to cater for all your needs. There is a large kitchen with... View all property information
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    Kissimmee, Central Florida 34746
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    1 / 41
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Children's Pool
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    About this property
    Caribe Cove in Kissimmee features a tranquil and serene atmosphere boasting all the luxuries for a memorable family vacation. After the parks, bask in the sun at the pool and spa, play a round of golf, or stroll the beautifully manicured grounds. The resort is ideally located within minutes to... View all property information
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    Kissimmee, Central Florida 34747
    1 / 49
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    * 24 hours man guarded gate. * two king, 2 full, 2 twin bed, enough for 8 to 10 * Additional folding beds will be provided upon request. * Elegant furnishings and decor * Fully equipped kitchen with stainless appliances and granite counters * Laundry with washer and dryer * Resort clubhouse with... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    9 Bedrooms, 5 Bathrooms, Sleeps 22 | Quick View
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    About this property
    If you’re looking for a large vacation home for your next getaway, then this beautiful property is for you. Located in the gated community of Champions Gate, this property boasts 9 bedrooms and 5 bathrooms to sleep a total of 22. The expertly designed kitchen is equipped with dark wood, granite... View all property information
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    Kissimmee, Central Florida
    1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The beautiful lakefront Westgate Vacation Villas offers easy access to Walt Disney World Resort, SeaWorld Orlando and Universal Orlando Resort, as well as the myriad of attractions, family-friendly restaurants and shopping opportunities along Highway 192. Guests enjoy 14 heated outdoor pools and... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    No need for a large 4 bed property when a nice 3 bed 3 bath pool town home will do....look no further. The recently updated home is located on one of the best town home lots in the community with a private back yard, no neighbors to the rear of the property and a very short walk to the... 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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    About this property
    “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 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    During the stay, if our guests would like to retain the bit of independence, than a stay in private Villa is ideal way to make it possible. Beautiful Disney Area Villa features private swimming pool, our guests can escape all thrills and spill down the roads and have ultimate family time,... View all property information
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    Kissimmee, Central Florida 34746
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Highlights; View Disney fireworks from the balcony Just 2 minutes from Oakwater clubhouse and pool Flat screen TV's throughout home Free high speed Wi-Fi Gated resort style community Full size Washer / Dryer Description; The Wishes vacation home is a cozy luxury 2 bedroom condo in Oakwater Resort,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Enjoy a simply perfect vacation in this beautiful 4 bedroom duplex located at the gated community Bella Vida Resort. Located just 7 miles from the Disney Theme Parks, close to shopping and dining on the 1-92 corridor, you're perfectly placed to enjoy your vacation your way. You can enjoy a day at... View all property information
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    Kissimmee, Central Florida 34746
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Le encantará esta casa de vacaciones increíble! Es un gran lugar para pasar el verano, el invierno y los días de fiesta! Le encantará sentarse en el porche y disfrutar de la naturaleza y la vida silvestre. Sus hijos les encantará las divertidas atracciones que se encuentran tan convenientemente muy... View all property information
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    Kissimmee, Central Florida 34758
    1 / 16
    4 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 3 bedroom pool home is located in the heart of Kissimmee, peaceful but also so close to the shops, restaurants and a 24 hour Walmart. You will find all the attractions are within easy reach of this home and local beaches not too far away when you want to take a rest from the hustle and bustle... View all property information
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    Kissimmee, Central Florida 34746
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    This Luxuriously appointed home is presented with upgraded furniture and fittings throughout, and fully air conditioned to create a comfortable indoor climate. With1 bedroom and bathroom located on the ground floor of the home, it is an ideal choice for groups with elderly or less mobile... View all property information
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    Kissimmee, Central Florida 34758
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Kissimmee, Central Florida
    1 / 11
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    2 bedroom 2 bathrooms Condo located at Cane Island Resort. Cane Island resort is a gated community so you and your family can spend a secure and fun vacation inside the resort. Only 3 miles from the magic of Disney World, with easy access to shopping places or have fun in the community pool of the... View all property information
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    Kissimmee, Central Florida 34746
    1 / 18
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Venetian Bay Villages is a gated luxury community with 24hrs security right in the middle of all the attractions Orlando can offer. Within 10 minutes you are at Disney’s main gate, 20 minutes drive to Universal Studios or Sea World, an hour drive to world’s famous beaches and Kennedy Space Center.... View all property information
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    Kissimmee, Central Florida 34741
    1 / 36
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Come stay in our newest Reunion addition to our home inventory This beautiful 3 story home with spectacular golf course view from all three floors is a must see The home has a gorgeous court yard pool for privacy during your stay Comes complete with garage apartment with sofa sleeper and games room... View all property information
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    Kissimmee, Central Florida
    1 / 25
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy a comfort of this 3 Bed 2 Bath villa in a great location minutes away from Disney! - Private Pool - Free Wi Fi - TVs in 2 Bedroom and Living Area - Beautifully Decorated - Fully Equiped Eat In Kitchen - Breakfast Bar This 3 bed 2 bath villa offers luxury, comfort, and serenity for you and... View all property information
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    Kissimmee, Central Florida 34758
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    3 Bed / 2 Bath Town Home With Your Private Screened In Patio<BR><BR>Our Luxurious and well maintained Town home is fresh renovated. This modern furnished and decorated 2 Story townhome with Cable TV, Free Wi-Fi, and Free Unlimited Local and US calls gives you all the convenience and comfort a home... View all property information
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    Kissimmee, Central Florida 34746
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    THIS DEAL ON THIS HOME IS NOT INCLUDED WITH ANY OTHER DEAL BEING OFFERED AND IS NOT INCLUDED IN THE 15% DEAL $105 plus 13% tax off season $115 plus 13% tax peak season NO PETS/ANIMALS ALLOWED - NO SMOKING ALLOWED FREE - INTERNET FREE - PAK N PLAY FREE - HIGH CHAIR This 3 bed 2 bath home is... View all property information
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    Kissimmee, Central Florida 34746
    1 / 64
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Newly decorated townhouse (November 2014) 145 sq.metres in secure gated community with heated pool, gym, tennis court & clubhouse. 1 hr 15 mins to Tampa Bay & Daytona Beach. 15 - 20 minutes to Theme Parks & 5 minutes to Kissimmee shops & restaurants. Beautifully decorated with wooden flooring... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Lovely 4 bedroom, 3 bathroom townhome with private pool located in the 5* gated resort community of Terra Verde. Located in Kissimmee just a few minutes from Disney theme parks. Terra Verde Resort has a beautiful clubhouse for guests enjoyment including a fitness room, business center, cards room... View all property information
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    Kissimmee, Central Florida 34747
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    6 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    The perfect home for your vacation in Florida! Have the vacation of your dreams in this beautiful 6 bedrooms and 6 1/2 bathrooms House with Game room and private Jacuzzi. It can accommodate up to 13 people very comfortably.The house also offers stainless steel appliances, granite countertops,... View all property information
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    Kissimmee, Central Florida 34741
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    This luxurious townhome has two stories, 1679 sq.ft., 4 bedrooms, 3.5 bathrooms The home comes with stainless steel kitchen facilities. There is a formal dining area that seats 4 plus with additional 2 bar stools located by the fully equipped kitchen. The interior is upgraded with laminate floor in... View all property information
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    Kissimmee, Central Florida 33897
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    The very cozy Key West-style gated resort offers a great lakeside setting in the heart of Kissimmee. The air-conditioned establishment has 40 guest rooms, children's playground and Internet access. The luxurious condos have fully equipped kitchens, a spacious living area, SPA tub and shower in the... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Disney private vacation condo, ground floor unit, in the beautiful resort of Windsor Palms, a private gated community with tons of amenities included, only 3 miles to Disney and other attractions. 3 BR/2 bath luxury with private heated Olympic size pool/Jacuzzi/ game room at the club house, with... View all property information
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    Kissimmee, Central Florida
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This large, exclusive 2700 sq.ft pool home was elegantly remodeled. There is new tile flooring throughout and the bedrooms have carpet. This home will accommodate up to 10 people plus baby. The family room has large sofa group and a 55" LED TV, cable with almost 100 channels and a CD-player with... View all property information
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    Kissimmee, Central Florida 33897
    1 / 32
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    Welcome to Florida! If you are looking for a vacation home near Disney, we are here to help! We have over 200 beautiful homes, from 1 bedroom condos to 10 bedroom pool villas, all just minutes away from Walt Disney World! <BR><BR>This beautiful 4 bedroom town home is located at Coral Cay, just 6... 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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    <h1 style="color: #76be43;">Luxurious Orlando Vacation Home in Paradise Palms Resort, Kissimmee, Florida</h1><ul style="margin:0; padding:0; "><li style="margin:0; padding:0 0 0 15px; background-image:... View all property information
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    Kissimmee, Central Florida 34747
    1 / 75
    4 of 5 stars (2) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    We know our Villa located 3.5 miles from Disney's doorstep will be the perfect fit for you and your family. We strive on one main item that many villa's do not, keeping it clean. When you walk into a villa you want to feel like its your home, clean and comfortable and unlike many other's that is... View all property information
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    Kissimmee, Central Florida 34747
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    Moon Lake House is a fantastic luxury home with three master suites and two bedrooms. The heated pool and spa are mere feet from Moon Lake. The first master suite is 45' long and has a king-size bed, two walk-in closets, and a sitting room. Its bathroom has a large soaking tub under a romantic... View all property information
    Location Information
    Kissimmee, Central Florida 34747