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Vacation Home Rentals and Villas in Kissimmee, FL

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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 stars (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    'Imagine Renting This Luxury Villa Overlooking The Beautiful Private Lake, In Orlando`s Most Prestigious Resort, Windsor Hills' This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The... View all property information
    Location Information
    Kissimmee, Central Florida
    5 of 5 stars Reviewed June 27, 2015
    Thank you for viewing this listing however this property is presently under new ownership and is no longer accepting short term rentals.
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Terra Verde Townhome with 3 bedrooms, 2,5 bathrooms, and private spa. Sleeps 8. Terra Verde is a resort style gated community within minutes from Disney, Universal Studios and Sea World. You will find yourself right in the middle of all the best experiences Orlando has to offer! Play and Rest!... 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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    Newly Renovated! 4 Bedrooms including: 2 Master bedrooms with King size beds and en suites 1 bedroom with Queen size bed 1 bedroom with double twin beds Games room with pool table and fos All rooms include cable programming with LCD TVs Screened Pool with Hot Tub and seating... View all property information
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    Kissimmee, Central Florida 34744
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This two story four bedroom three and a half 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... View all property information
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    Kissimmee, Central Florida 34746
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Relax In Your Own Private Pool, Take a Stroll By The Natural Pond & Fishing Pier...... Or Visit The Clubhouse!! This beautiful new and tastefully appointed townhouse is close to the 9000 sq.ft club house which features 2 large pools, 2 hot tubs, cyber room, concierge, exercise facility, lakefront... View all property information
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    Kissimmee, Central Florida 34747
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spacious and comfortable luxury living at fabulous nightly rates This 4 bedroom home provides a perfect option for families looking for something special in the Disney parks area The nostalgic charm of the wooden boarded beach front style properties on Fairview Circle presents discerning guests the... View all property information
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    Kissimmee, Central Florida 34747
    1 / 15
    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The terra cotta and deep green colors in the living/dining/kitchen area make the villa warm and inviting. Every bedroom has its own splash of color; sunny yellow, serene blue, deep sea teal, and sandy beach tan. Venetian Bay Villages is just off HWY 192, in Kissimmee, Florida and is perfectly... View all property information
    Location Information
    Kissimmee, Central Florida 34741
    4 of 5 stars Reviewed June 16, 2011
    We have stayed in this location many times. Improvements have been made to the unit, all good and necessary for the tennants. Close to the Club house and pool. Appreciate the...
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Reunion Resort Completely Remodelled 6 Bed Games Room Pool Spa Stunning Golf Views This fantastic Reunion Resort home has just been completely remodelled decorated and furnished The decor and furnishings are modern and contemporary with beautiful finishes Boasting 5000 sq ft this home also offer... View all property information
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    Kissimmee, Central Florida 34747
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Chatham Manor is located within the Chatham Park Community, This home has 3 bedrooms and 2 and a half baths. It also features a loft with a pull out couch to help accommodate additional guests. This home is situated on a retention pond and offers a lovely lake view to enjoy when out in the private... View all property information
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    Kissimmee, Central Florida 34746
    1 / 16
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This Excellent Vacation Home is of the Excellent Superior category. The villa is situated close to Osceola Parkway which allows for easy access to the SR417 (Greeneway) and Florida's Turnpike too. The villa is therefore only minutes to the Walt Disney World, Universal Studios, Sea World theme parks... View all property information
    Location Information
    Kissimmee, Central Florida 34743
    5 of 5 stars Reviewed September 5, 2013
    House in a very good location;the organization top notch,preparation for arrival all right on time..Thank-you
    4 of 5 stars Reviewed July 4, 2013
    Nice property with own Pool. Highway & Planes are a bit too loud, nevertheless we enjoyed our stay.
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    The exterior of this outstanding contemporary home has a South Florida style with amazing custom designed metal and glass doors accessing the entrance with the atrium of two floors The natural stone floor continues into the great room which is open plan and flows beautifully between the living area... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    COME AND ENJOY THIS DREAM VACATION HOME TODAY! Delightful townhouse with 4 bedrooms and 3 bathrooms, located just 10 minutes from Disney Parks! This lovely home has a large living space with 1,856sq. A large east facing heated pool with sizes of 26x13' and a 6' depth with a lake view in the back.... View all property information
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    Kissimmee, Central Florida 34741
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Welcome to Windsor Palms Resort and this stunning 6 bedroom, 4 bathroom (2176 sq.ft.) rental home located near the theme parks in Orlando, with Florida. This vacation rental home has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense... View all property information
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    Kissimmee, Central Florida 34747
    1 / 37
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    This home offers luxury with modernity featuring fresh and clean style. The home has been fully upgraded appliances with high end art pieces and decor. The space feels open and airy with a spacious living room, conversation area, dining and fully equipped kitchen. The main living area opens to your... View all property information
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    Kissimmee, Central Florida
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Welcome to the perfect house for your dream vacations!! This beautiful and luxury (6 Bedrooms 6 and a half bathrooms) brand new pool house Is professionally decorated. It has a private pool and spa (optionally heated - fee applies), It is fully equipped, with high quality furniture, the house is... View all property information
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    Kissimmee, Central Florida 34741
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Oakwater Resort and this stunning 3 bedroom, 2 bathroom (1417 sq. ft.) rental located near the theme parks in Orlando, Florida.  This vacation rental has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense to dine in. And,... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ONE OF THE CLOSEST COMMUNITIES TO DISNEY Luxury 4 bedroom villa in a superb location genuinely only a few minutes drive from Disney 4 bedrooms Games room including 91 pool table electronic darts foosball air hockey and table tennis One of the closest communities to Disney PS2 stereo iPod dock Wi Fi... View all property information
    Location Information
    Kissimmee, Central Florida 34747
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    1 / 40
    4.5 of 5 stars (5) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    *** Please note that the rates and availability on this website are for guidance only. Accurate availability and rates can be found on our Official company Website - www.villa.us or by calling us at: 407-738-7712 *** This beautiful 1400 Sq Ft town home is located in the 5-star premier community,... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    4 of 5 stars Reviewed 5 days ago
    Despite a late change made by the Owners / Managing Agents from Celtic Palms to Fiji Palms, both properties in the same gated community of Windsor Palms, we were very satisfied...
    5 of 5 stars Reviewed July 6, 2015
    I loved this home, it was very clean and spacious. My children loved the indoor pool and enjoyed the amenities , The arcade and bar near the pool was a bonus. I would highly...
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Magical Dreams is perfectly placed in the Somerset Community, just 12.5 miles away from Walt Disney World in Kissimmee. With 5 Bedrooms and 4.5 bathrooms, this superior and spacious vacation home is perfect for extended family vacation groups, sleeping up to 12 guests. The oversized pool is a... View all property information
    Location Information
    Kissimmee, Central Florida 34744
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Encircled by a protective and protected buffer of woodlands and wetlands Windsor Hills Resort is a land island amidst a sea of lush vegetation The winding palm lined road that leads you to Windsor Hills Resort is a prelude to the community s grandeur The colonnaded entry provides a dramatic sense... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    5 of 5 stars (1) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Visit our owner website at the bottom of the page to view our 360 degree walk-through video: This is a a beautiful Mediterranean style property which has been designed, built and decorated to be the amongst the best. With 6 bedrooms and 5 1/2 bathrooms this is the perfect choice for all holiday... View all property information
    Location Information
    Kissimmee, Central Florida FL 34746
    5 of 5 stars Reviewed April 30, 2012
    Fantastic, clean well maintained villa so near to Disney & Universal. We have just finished 22 days from 27th March to 18th April 2012 in the villa. The resort is idealy...
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Very Spacious home in a 24 Hour Gated Resort Community. This home is perfect for family gatherings. This home offers 4 bed - 3 bath private pool vacation home in the Terra Verde resort. The home has a conservation view for your relaxation. Situated just off 192 and just 15 minutes from Disney.... View all property information
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    Kissimmee, Central Florida
    1 / 14
    4.5 of 5 stars (7) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Gorgeous 4 bedroom house minutes from Walt Disney World. Have your own private pool and a fun game room the whole family can enjoy. Close to I-4 access for travel to Universal Studios and Sea World. If the ocean is your thing, you can get to either coast within an hour of driving. View all property information
    Location Information
    Kissimmee, Central Florida 34747
    4 of 5 stars Reviewed July 5, 2015
    The owners were excellent to deal with and gave us great directions from the airport to the house. This was our first condo rental and it was a great experience. The house was...
    5 of 5 stars Reviewed June 30, 2015
    The house had everything we needed in a nice location. Just thought it would be better to have a scrubbed pool and clean comforters, but overall I was satisfied with the price...
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    This is a beautiful 7 bedrooms / 5 full and 2 half bathrooms. The home is perfectly located in the quiet gated community of Cumbrian Lakes. The home has a fabulous view of one of the lakes in the community which is south facing. This house has just been upgraded with all new furniture and has... View all property information
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    Kissimmee, Central Florida 34746
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This fantastic Tuscan themed Sub Division is located just off the Westside Blvd area of Kissimmee, just off the Highway 192 and surrounded with restaurants, bars and supermarkets, the sub division is minutes away from the West Gate entrance at Walt Disney World Resort. The homes benefit from first... View all property information
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    Kissimmee, Central Florida 34747
    4 Bedrooms, 11 Bathrooms, Sleeps 8 | Quick View
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    • Private Yard
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    Upscale 4 bed 4 baths home with enclosed pool is the perfect place to relax after a long day at the parks. This beautiful pool home is 4 bedrooms 4 bath, located in the most sought after gated resort community of Bella Vida about 10 miles from Disney World. This home will host up to 8... View all property information
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    Kissimmee, Central Florida 34746
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This fantastic Tuscan themed Sub Division is located just off the Westside Blvd area of Kissimmee, just off the Highway 192 and surrounded with restaurants, bars and supermarkets, the sub division is minutes away from the West Gate entrance at Walt Disney World Resort. The homes benefit from first... View all property information
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    Kissimmee, Central Florida 34747
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    6 BEDROOMS 4 BATH 2 STORY VILLA – WINDSOR HILL Look no further! You found the perfect Orlando vacation villa! This spectacular 6 bedroom 4 full bathroom villa has everything you’ll need for your next vacation. The villa provides 2812 square feet of comfort. The villa contains all high end... View all property information
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    Kissimmee, Central Florida
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to Oakwater Resort and this stunning 3 bedroom, 2 bathroom (1417 sq.ft.) rental located near the theme parks in Orlando, Florida.  This vacation rental has all the comforts of home and more.  The kitchen is fully furnished and ideal for those times when it makes sense to dine in. And, there... View all property information
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    Kissimmee, Central Florida
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Brand New! 3BR 2BA Luxury Condo Just minutes from Disney This brand new and luxurious condo is more than just a home away from home. Every possible service and amenity is provided both within the condo and at the nearby Windsor Hills clubhouse. The master bedroom suite features a king size bed,... View all property information
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    Kissimmee, Central Florida 34747
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3Bedroom & 2 Bath Townhouse in gated community. The house is very well kept & clean. The house and complex offer a great place for families to stay and enjoy your vacation. LOCATION, LOCATION, LOCATION! The house is in a great location. You can avoid major traffic routes and are still very... View all property information
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    Kissimmee, Central Florida 34746
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    The Apartment: Cozy 3 bedroom vacation apartment located in one of the best areas in Orlando, less than 8 kms. to Disney World Main Gate and close to Sea World, Universal Studios, Islands of Adventure and the rest of the attractions that proposes this beautiful city. This practical vacation... 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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    This classic four-bedroom Kissimmee vacation rental is just six miles to Walt Disney World Resort and offers resort amenities for up to eight guests! Plan a family reunion or take your children to sunny Orlando which offers both Sea World and Universal Studios just 20 minutes away. This vacation... View all property information
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    Kissimmee, Central Florida 34746
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    5 Bedrooms, Sleeps 10 | Quick View
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    Floor Plan (The Spencer) 2,966 sq. ft. 2 story home with pool and spa. (South facing pool) We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with... View all property information
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    Kissimmee, Central Florida 34747
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BEDROOM CONDO KISSIMMEE Booking Code = [propertyid] Additional amenities include: communal gym, TV in every bedroom, paved parking, free calls, fully equipped kitchen and laundry facilities, two resort pools, has spa, conservation view, has pool, short drive to disney and other attractions,... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This vacation home holiday rental is a fantastic 4 bedroom 3.5 bathrooms that comfortably accommodates up to 10 guests. This two story townhouse is located in the Regal Oaks resort just 10 minutes away from Disney and seconds from Hwy192 with all shops and restaurants right on the strip. The... View all property information
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    Kissimmee, Central Florida 34746
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    The minute that you open the door to this four bedroom/ three bathroom townhome in Paradise Palms Resort the neutral Earth-toned colors dominate the interior walls while unique decorative pieces bring the rooms to life. Going out the back sliding door of this beautiful two story home will lead you... View all property information
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    Kissimmee, Central Florida 34747
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    AMAZING CUSTOM BUILT 6 BEDROOM REUNION RESORT HOME This outstanding home has been a private residence on Muirfield Loop within the Reunion Resort and so boasts numerous upgrades throughout the home The main house has five bedrooms three on the ground floor and two upstairs The separate guest house... View all property information
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    Kissimmee, Central Florida 34747
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    5 of 5 stars (6) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Set on an attractive, secure private estate, our beautifully decorated and furnished villa is perfectly situated for all Orlando area holidays. Situated less than ten minutes drive of the Walt Disney Resorts, the villa is also minutes from a wide selection of restaurants, supermarkets, golf clubs... View all property information
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    Kissimmee, Central Florida 34747
    5 of 5 stars Reviewed June 18, 2013
    everything so clean and tidy on arrival.the card and wine made it that little bit more special.pool and hot tub were used on a regular basis!having stayed on indian ridge many...
    5 of 5 stars Reviewed December 12, 2010
    Service from owners(Suzanne & Graham) and Loyalty was excellent. We felt welcomed and looked after. The villa was very clean and had everything we expected and more. The villa has...
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    This brand new Platinum Collection home on the new superb Emerald Island Resort, Kissimmee features a tranquil and relaxing atmosphere boasting all the luxuries to make a memorable family vacation. Simply put, it is a stunning brand new home in the heart of the Magic Orlando has to offer. The... View all property information
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    Kissimmee, Central Florida 34747
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your family with the... View all property information
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    Kissimmee, Central Florida 34747
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    We are pleased to offer a Luxury vacation home in a tranquil setting with every possible luxury for your private enjoyment all within minutes drive from local attractions such as Walt Disney World Universal Studios Golf Courses and more Our Villa is custom built and furnished appointed with your... View all property information
    Location Information
    Kissimmee, Central Florida 33837
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Overview 1. Planning a Disney vacation and looking for a vacation home that accommodates up to 12 guests? We have a great option for you. It's spacious, comfortable, near Disney parks and inside a great resort community: Paradise Palms, Kissimmee. You will fall in love with this 5 bedrooms, 4... View all property information
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    Kissimmee, Central Florida 34747
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    'Imagine Renting This Stunning Villa with a private pool, In One Of Orlando`s Most Prestigious Resorts, Windsor Hills' This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The... View all property information
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    Kissimmee, Central Florida
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    5 of 5 stars (4) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Kissimmee, Central Florida 34746
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This unit is a 3 bed 2 bath condo features nearly 1400sqft of living space and is fully equipped with everything that you will need for your vacation. Fully air conditioned and furnished to an individual style by the owners. Towels and linens are provided; you will only need to bring your beach... View all property information
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    Kissimmee, Central Florida 34746
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    'Imagine It...You and Your Family Renting a 5-Star Florida Holiday Villa on Legend Corner, Reunion Resort, with a Private Pool & Spa, Only 12 Minutes from Disney World' Villa W074 Muirfield Loop, Reunion Resort, Orlando, Florida TYPE: VILLA | BED: 5 | BATHROOM: 5.5 | SLEEP: 10 | POOL: YES |... View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Kissimmee Vacation Rentals

    Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

    Kissimmee Vacation Rentals for Families

    More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

    Advantages of renting a vacation home in Kissimmee

    Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

    Rent a vacation house with a pool in Kissimmee, Florida

    How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

    Rental deals in Kissimmee

    Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

    Kissimmee and Orlando beyond Disney

    Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.