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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 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Great familly vacation villa consisting of 4 bedrooms and 3 full baths located less than 3 miles from Disney in the Gated Community of Windsor Palms. Large southwest facing pool with no rear neighbors and sun all day.Two master suites with ensuites and 2 twin rooms with shared full bath. Infant and... View all property information
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    Kissimmee, Central Florida 34747
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Our villa is located in Emerald Island Resort. It is over 3000 sq feet and has a very private back yard. It is not facing any other houses, it overlooking peaceful pond and conservation area. This 7 bedroom/4.5 bathroom house has 3 king beds, 2 queens, 4 twin beds. This house can sleep 14 peoples.... View all property information
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    Kissimmee, Central Florida 34747
    1 / 52
    5 of 5 bubbles (7) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Once your family sees this amazing pool area, they'll never want to leave! The private 30ft x 14ft pool and spa has a large, extended decking area around it and is complemented by a 40ft x 10ft porch providing some shade. And you won't believe the view! All towels and bed linen will be supplied. If... View all property information
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    Kissimmee, Central Florida
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Indulge in Orlando areas finest accommodations without breaking the budget. Enjoy spacious living while on vacation in a 2 bedroom 2 bathroom condo! Ditch the cramped hotel room. Make your week in the Orlando area even more memorable! Go ahead and reserve now to start creating your happy... View all property information
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    Kissimmee, Central Florida 34747
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Contemporary Deluxe 3 Room Disney Celebration Resort Villa Suite (approximately 540sf) sleeping up to 6 people with Discount Park Ticket, Golf & SPA - Located in the heart of Disney World right in between Disney Celebration & Downtown Disney! We offer the ultimate in convenience, comfort of home,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 bedroom condo that sleeps 4: Mystic Dunes 2 Bedrooms are available at additional cost, must ask for further details. Outdoor pools and golf course on site, Close to Disney and Universal attractions. Bedroom- bathroom- living room with pull out couch and kitchen Must be 21 years to rent View all property information
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    Kissimmee, Central Florida 34747
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Please be advised that this home is not located in Orlando, Fl. The location of this home is in Lucaya Village near Old Town on Polynesian Isle Blvd, Kissimee, FL. This amazing 3 Bedroom/2 bath apartment comfortably accommodates up to 6 guests. This updated modern home consists of 2 Kings, and 2... View all property information
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    Kissimmee, Central Florida 34746
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    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    SPECIAL FOR SEPTEMBER ONLY. 2 GUESTS ONLY, INCLUDING INFANTS AND CHILDREN. $49/NIGHT PLUS 13% TAX. Beautiful 3 bedroom/2 bath condo with community pool and spa. Located only 7 minutes from Disney entrance. Come relax after a hard day of fun at the attractions! Everything you need for a relaxing... View all property information
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    Kissimmee, Central Florida 34746
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: communal gym, TV in every bedroom, paved parking, resort facilities including 2 pools, fitness center tiki bar, fully equipped kitchen and laundry facilities, free calls, short drive to disney and other... View all property information
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    Kissimmee, Central Florida 34746
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Fully furnished and equipped with quality and tasteful furniture this 4 bedroom 3 bathroom home is just perfectly located in the beautiful Emerald Island Resort, the perfect community to base your Florida vacation. The family room in the home has comfortable sofas and a large flat screen TV and... View all property information
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    Kissimmee, Central Florida
    1 / 37
    4.5 of 5 bubbles (21) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    The Magnificent 4 Bedroom 2 Bath King Triton’s Castle Highlights: Spacious Fully Furnished Home with pool,spa, screened lanai . Cathedral Ceiling in Living Room overlooking beautiful pool area. Newly refurbished and decorated. Computer with high-speed Internet and Wireless for your laptop. Flat... View all property information
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    Kissimmee, Central Florida
    1 / 22
    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Short Stays (less than 7 nights) incur a cleaning fee. Stays of less than 5 nights have to pay a refundable damage deposit. Stays 5 nights or more can pay the Damage Waiver instead of the damage deposit. 4 Bed 3 Bath Luxury Pool Home 10 mins from Disney A Premier Gated Community in a... View all property information
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    Kissimmee, Central Florida 34746
    1 / 60
    8 Bedrooms, 9 Bathrooms, Sleeps 20 | Quick View
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    “Imagine You and Your family renting this beautiful Private Villa which Sleeps 20 with a private pool, a Games Room & so much more, located on Reunion Resort in Orlando, only 6 miles from Disney World. This Vacation Rental is perfect for you and your family & friends to have a great time” With over... View all property information
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    Kissimmee, Central Florida 34747
    1 / 104
    5 of 5 bubbles (123) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Minutes away from attractions. Miles away from stress. Situated in the heart of Orlando's most sought-after destinations is an incredible resort community, Encantada. Around the corner from the Walt Disney World® gates, and minutes from other Orlando theme parks, you'll be amazed at how close this... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Just minutes from Disney World, but miles from the mundane, is Bella Piazza, an enchanting community that captures the magic that is Orlando, Florida. Designed with the charm of a Mediterranean village, Bella Piazza is an elegant, yet affordable priced, holiday retreat where everything you love... View all property information
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    Kissimmee, Central Florida
    1 / 33
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: TV in every bedroom, paved parking, communal gym, fully equipped kitchen and laundry facilities, free calls, resort facilities including 2 pools, fitness center, tiki bar, short drive to disney and other... View all property information
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    Kissimmee, Central Florida 34747
    1 / 44
    5 of 5 bubbles (23) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Simba's Sunset is a 7 Bedroom, 5 Bathroom, 3354 sqft, 2 Story Pool and Spa Home in the executive gated community of Formosa Gardens. Famous for large lots, this home is no different, plants and a fence keep this pool area totally private. The pool is west facing so you get to enjoy some gorgeous... View all property information
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    Kissimmee, Central Florida 34747
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    1 / 23
    5 of 5 bubbles (5) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Luxurious 6 bedroom and 4.5 bathroom villa with large private pool and spa, fully equiped games room, fitness area and high speed internet access. Less than 10 minutes from Disney World. This elegant vacation villa offers six bedrooms (2 Master, 2 Queen, 2 Twin) and 4.5 bathrooms with... View all property information
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    Kissimmee, Central Florida 34746
    1 / 18
    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Best luxury house in Windsor Hills Resort!! Our 6 bedroom 4 bathroom Disney Dream House. The largest most luxurious home in the 5 star gated resort of Windsor Hills! Just 2 miles from the gate of Walt Disney World! Our home features - South facing private pool and spa. Top notch electronic... View all property information
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    Kissimmee, Central Florida 34747
    1 / 28
    5 of 5 bubbles (1) Excellent
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    Spacious & Tastefully Furnished 5BR 4.5 BATH Villa -3 Master Suites, large deck, private pool & Spa, close to DISNEY This bright and spacious Villa is tastefully decorated and located conveniently close to Shopping, Dining and all major attractions. On the ground floor you will find the living... View all property information
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    Kissimmee, Central Florida 34746
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The elegance of wrought iron is showcased in both the fencing and the balcony railings of this 2762 square foot Mediterranean style home. Inside, the first floor has an open and airy feeling as each area effortlessly blends from one to another. Made for entertaining. The wall mounted 50 inch TV is... View all property information
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    Kissimmee, Central Florida 32805
    1 / 45
    9 Bedrooms, 6 Bathrooms, Sleeps 24 | Quick View
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    About this property
    GRAND OPENING of a brand new luxury villa sleeping 24 people! 9 Bedrooms with 4 en-suites, 6 full Bath rooms, 4400+ sqft Living Space, Games Room, Pool/Spa located in a sort-after gated vacation community - Windsor at Westside - 9 Bedrooms (4 King Rooms en-suites, 2 Queen, and 2 Twins Room... View all property information
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    Kissimmee, Central Florida
    1 / 24
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Spread out and enjoy your very own sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World!<BR><BR>NO REAR NEIGHBOURS! To ensure your privacy, we chose a premium location that overlooks a natural area, not another home or... View all property information
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    Kissimmee, Central Florida 34747
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Westgate Vacation Villas Resort & Spa offers the finest in luxury accommodations just minutes from the main entrance to Walt Disney World® Resort and within close proximity to Universal Orlando® Resort and SeaWorld® Orlando.With more than 2,800 luxury villas, ranging from efficiencies to... View all property information
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    Kissimmee, Central Florida 34747
    1 / 29
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Rolling Hills, Kissimmee, Florida. Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. Watch Netflix movies via blu-ray DVD player in the living room. HD TV in living room and all bedrooms,... 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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    “Lake Berkley Villa Beautiful 3 bedroom On Oversized Corner Lot With Private Pool 3 Bedroom, 2 Bathroom villa sleeps 6 A luxurious 3 bedroom villa with private heated (upon request) pool on Oversized Corner Lot. Situated in one of the most sought after resorts, the impeccably manicured and... View all property information
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    Kissimmee, Central Florida 34746
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Gorgeous fully furnished 4 bed 2 bath corporate rental apartment Orlando, FLLocation: Legacy DunesAbsolutely gorgeous, 4-bed, 2-bath condo located in the fabulous Resort Style privately gated community of Legacy Dunes. It comes fully furnished to accommodate 8 persons very comfortably with top... View all property information
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    Kissimmee, Central Florida 34747
    1 / 18
    7 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Formosa Gardens Estates is the only luxury, exclusive, gated community within two miles of Walt Disney World. This luxury, upmarket home is perfectly situated. Just minutes from Disney and golf and within walking distance of shops and restaurants in the Formosa Shopping Village. This community... View all property information
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    Kissimmee, Central Florida 34747
    1 / 17
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Our professionally decorated 5 bedroom, 3 bath single story vacation home will surpass anyone?s needs, dreams or expectations. The kitchen is fully equipped with ice maker, microwave, coffee maker, dishes and all the utensils to make your vacation a home away from home. There are 2 living areas... 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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    The Pocahontas Villa Retreat is a beautiful 3 bedroom 2 bath modern home with all tile. It has a sparkling private pool - under umbrella table & chairs and BBQ Grill. Enjoy the modern eat in Kitchen that overlooks The family room featuring a large Flat Screen TV and DVD Player. Gaze out at the... View all property information
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    Kissimmee, Central Florida 34747
    1 / 14
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Venetian Bay Villages is just off HWY 192, in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that Orlando has to offer. Venetian Bay is ideally located as a "home base" for other Florida activities including the Space Coast or the Gulf Coast. With 3... View all property information
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    Kissimmee, Central Florida 34741
    1 / 52
    5 of 5 bubbles (37) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Just a pixie dusts throw away from Disney, this beautiful townhome with 3 bedrooms and 2 1/2 bathrooms is located at the gated Fiesta Key Resort in Kissimmee. This townhome is perfect for families, business travelers, retirees, snowbirds, golfers, singles or couples. This home comes complete with a... 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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    This is a beautiful vacation rental home 5 minutes from Walt Disney World in Kissimmee, Florida. It has 4 bedrooms and 3 full bathrooms. This spacious villa sleeps 9 people in total comfort. The functional floorplan boasts a bright, open living area with separate dining area and kitchen. Our... 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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    Beautiful 2 story vacation luxury house. Master bedroom with king size bed, balcony and private bathroom. Second and third bedrooms with queen size beds. Two bedrooms with twin size beds (first floor with 1 bedroom with twin beds). Home computer with Internet/wifi service and all local/long... View all property information
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    Kissimmee, Central Florida 33896
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • Waterfront
    • DVD Player
    • Hot Tub
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    This 7-bed, 4.5-bath Kissimmee home can comfortably accommodate 14 guests throughout its well-equipped interior. Situated in an ideal lakefront setting, this property allows you to admire fantastic views while swimming in the private pool! Lush, green landscape surrounds this phenomenal Florida... 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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    • Satellite TV
    • Patio
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    • Outdoor Dining Area
    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This newly refurbished villa and pool is ideal for Disney and Universal Holidays. It has a Super HD television, and an HD television in the two en-suite bedrooms. The Lanai is in a cage and faces West for warm lazy evenings by the pool after hard days enjoying the parks. You can dine in, or dine... View all property information
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    Kissimmee, Central Florida 34746
    1 / 33
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • ?
    About this property
    Highlights; Beautiful pool and games room Free high speed Wi-Fi Flat screen TV's throughout home Close to main clubhouse and pool Gated resort style community Full size Washer / Dryer Description; Vacation in style with this excellent vacation home in the highly sought after resort of Windsor... View all property information
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    Kissimmee, Central Florida 34747
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Hot Tub
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Sauna
    • DVD Player
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This is a newly renovated 1650 SF unit with an open floor plan. Well appointed modern furnishings with ceramic and porcelain flooring throughout. This is ideal for allergy sufferers. The four bedrooms contain 1 King, 2 Queen and 2 twin beds, respectively. There are three full bathrooms, and a... View all property information
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    Kissimmee, Central Florida 34747
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Only 4 miles to Mickey's front door! 3 Bedrooms, 3 Bathrooms, Sleep 8, Free Wifi, Nintendo Wii, Baby Ready! You will say "this place is amazing" the moment you arrive at your Paradise Cay vacation townhome, just 1 of 3 units that we have available in this wonderful resort! If you are... View all property information
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    Kissimmee, Central Florida 34746
    1 / 50
    4 of 5 bubbles (9) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Internet Access
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Mickey's Movie House is one of our most popular Kissimmee vacation homes! Located in the quiet Indian Ridge Oaks neighborhood, just 4 miles from Disney World, you'll instantly fall in love with this stylish home. As you arrive at Mickey's Movie House, the kids will see the Mickey Mouse face in the... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Wonderful 4 Bed townhome with 3 Baths, located at Paradise Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with fitness center,... View all property information
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    Kissimmee, Central Florida 34747
    1 / 17
    4.5 of 5 bubbles (25) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Porch
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    This spacious townhome with 3 bedrooms, 3 bathrooms is located in Kissimmee in a safe and secured Gated Resort Community, off Route 192. The house is minutes away (1.5 miles) from Disney parks, 20 minutes from Sea World and Universal Studios. Super Target, Wal-Mart and Orlando Premium Outlets are... View all property information
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    Kissimmee, Central Florida 34747
    1 / 29
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Patio
    • Central Heating
    • Hot Tub
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Why hassle with overpriced resorts and hotels if you can have a luxurious vacation experience in the comfort and privacy of your own house? Welcome to the ultimate vacation villa - It's been furnished to the highest standard! When you first walk in the front door, you'll be greeted by the open... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    This is a two storey, tastefully furnished and spacious villa with fully screened in private pool (heating available). Property has 5 bedrooms and 3.5 bathrooms and benefits from having two separate games rooms Master Bedroom: King bed, 18' flat screen/DVD player Master Bathroom: 2 double closets,... View all property information
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    Kissimmee, Central Florida
    1 / 40
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Beautiful house made ​​especially for you!​ Have the vacation of your dreams in this beautiful 6 bedrooms and 4 1/2 bathrooms house. It can accommodate up to 14 people very comfortably. The house also offers washing machine dryer, a full kitchen, bed and bath linen, WiFi, cable TV, telephone, a... View all property information
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    Kissimmee, Central Florida 34746
    1 / 27
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • ?
    About this property
    This beautiful Two Story 5 Bedroom 4 Bathroom home located in the much requested Gated Community of West Haven, is just right for your family's next vacation. Your vacation home has many special touches to make you feel right at home. A Tiled Foyer and Main Area downstairs, brings all the luxury... View all property information
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    Kissimmee, Central Florida
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This 2 bedroom, 2 bathroom first floor condo is in the luxurious gated resort community of Windsor Hills Resort just outside the Magic Kingdom. This condo is fully furnished and well appointed with all housewares, linens, tropical and Disney themes, flat panel LCD televisions, DSL high-speed... View all property information
    Location Information
    Kissimmee, Central Florida 34747