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Kissimmee Holiday Rentals, FL

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    $156
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Floor Plan (Sonoma) 1st floor condo: 1,247 sq. feet Newly decorated, painted and upgraded 1st floor 3 bedroom, 2 bathroom condo located in the beautiful Windsor Hills manned gated community just 2.5 miles from Disney property. The home comes with a 42' flat screen TV in the living room with a... View all property information
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    House Rental - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    Floor Plan (Saddlebrook) 1,600 sq. ft. 2 story townhome with splash pool (South facing splash pool) Welcome to this elegant, and professionally decorated Orlando vacation townhome, located in the beautiful Windsor Hills Resort. This property features all the comforts of home and more! Windsor... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Floor Plan (Sonoma) 1,247 sq. ft. 1st floor condo Book your Orlando vacation rental now at this beautiful 1st floor condo in the Windsor Hills Resort. This 3 bedroom, 2 bathroom, 1,247 sq feet unit sleeps 6 in style. With 1 king bedroom, 1 queen bedroom and 2 twin beds, there is plenty of room... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Gardenia floor plan (2 floors) 3 bedroom, 2.5 bath, 1417 sqft. This beautiful professionally decorated condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. The 4,000 square foot Oakwater clubhouse features a lagoon-style pool, tennis, volleyball and... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Welcome to our Florida vacation condo. We invite you to enjoy our great property at Oakwater, built in 2007. This complex is one of the closest to Walt Disney World. I drove from the door to the gates of Disney and it took me 4 ½ minutes. It is also close to plenty of restaurants, shopping and... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Hello and Thank you for considering our Orlando Vacation Home. Our 3 bedroom, 2 bathroom, 1455 sq. ft. 2nd floor Condo sleeps 8 comfortably. It has been completely repainted, carpets cleaned and all new furniture, new beds (1 king size, l queen size, 2 twins, and pull out couch.), new linens, new... View all property information
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    $498
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    House Rental - 
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Pool Table
    • Private Fishing...
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    About this property
    Let us show you how a vacation with us could be the perfect choice for you and your family. We'll help you create lifelong memories that will make you want to return again and again and again. With 9 years under our belt already, we're in for the long haul, so we'll be right here to welcome you... View all property information
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    $354
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    House Rental - 
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Hot Tub
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    About this property
    Floor Plan (Sheldon) 1,816 sq. ft. 1 story home with pool and spa (North facing pool) Windsor Hills Reserve just 1.5 miles to Disney gates. Luxury 4 bed, 4 bath home, with private pool/spa and attached game room, is beautifully decorated and furnished with many upgrades. Accommodates 10... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    3 bedroom 2 bath (1,417 sq ft) Gardenia This lovely condo consists of one king bed, one queen bed and two twin beds, all bedrooms equipped with TV and DVD, PlayStation 2, high speed wireless internet access, and fully equipped kitchen. This property features all the comforts of home and a... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This beautiful 3 bedroom/ 2 bath condo is located in the beautiful gated community of Oakwater, located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts, basketball courts, and attraction shuttle. This newly furnished condo consists of... View all property information
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    Villa - 
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Gym
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    • Private Outdoor...
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    About this property
    LUXURY FAMILY VILLA WITH HUGE SPLIT LEVEL DECK AND FANTASTIC FREEFORM POOL AND SPA ONLY 5 MINUTES DRIVE TO DISNEY Luxurious and private 4 bedroom 2 bathroom villa sleeps eight Fully air conditioned Very private 36 x 22 max freeform pool and spa Huge split level sun deck with padded loungers all day... View all property information
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    1 / 23
    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Balcony
    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
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    • x
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    About this property
    10 great reasons to choose villa de Santa Maria as your Florida vacation accommodation 1. Close to all the major theme parks 2. Extra wide driveway for parking 3 cars 3. Private pool area...no neighbor views 4. Air-conditioned game room 5. Screened in front entry porch 6. Tiled... View all property information
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    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    This beautiful holiday rental apartment is a 3 Bedroom / 2 Bathroom vacation apartment home comfortably sleeps 6 guest. 3 Bedroom with a balcony with a great view is so relaxing and peaceful with contemporary decor, modern and updated furniture along with brand new appliances and very spacious... View all property information
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    $254
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    Villa - 
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Gym
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    About this property
    Look no further! You found the perfect Orlando/Kissimmee 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 furnishings. There are 2 king en suites, 2... View all property information
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    $126
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    House Rental - 
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This privately managed home, allows you to feel at home in 'magical Orlando' at the very best location at the very best price! Our villa is the former model home of Seven Dwarfs. Situated in the best upscale gated resort is Kissimmee's newest and most desirable residences. The incredibly charming... View all property information
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    $491
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    House Rental - 
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Hot Tub
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    • Private Outdoor...
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • x
    About this property
    Serendipity at Indian Creek is the essence of tranquility and luxury. We pride ourselves on going that extra mile to provide the finishing touches and attention to detail that turns an ordinary home into your very own personal vacation haven. Our spacious Orlando vacation home is nestled in the... View all property information
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    1 / 19
    5 of 5 stars (4) Excellent
    Villa - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Washer
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxury pool furniture - 2 padded... View all property information
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    $305
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    Villa - 
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Pets allowed
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    About this property
    This fabulous 6 bedroom vacation home-away-from-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... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    About this property
    Welcome to Indian Ridge Trail South! This well equipped 3 bedroom, 2 bath home is well furnished and has everything you need for a comfortable stay. Come home from a long day at the parks to your vacation home with incredible swimming pool and spa. As you enter the home you will find the... View all property information
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    Apartment - 
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Rental of Huge Lockout 1 BR Deluxe Condo during DAYTONA CAR RACE WEEK, February 21-28, 2014. Where: Westgate Town Center, 2770 Old Lake Wilson Road, Kissimmee, FL 34747 Building: 4000 - Sleeps: Four (4) Wonderful Resort Just One Mile from The Walt Disney World Resort, overlooks beautiful lake.... View all property information
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    $191
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    House Rental - 
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Waterfront
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    About this property
    Beautiful house close to Disney ideal for your holidays. View all property information
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    $89
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Gym
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    • Satellite TV
    • Washer
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Minutes away from Disney, our two floor townhome located in Fiesta Key gated community has all new furnishings with cherry hardwood flooring on the main floor. With an open floor plan you and your family will have plenty of space to enjoy all of the luxuries our townhome has to offer. On the main... View all property information
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    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • x
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    About this property
    Star Island is your pick for centrally located superior accommodations. Valued guests enjoy everything Orlando has to offer including thrilling theme park attractions, restaurants, shopping centers, golf courses and outdoor adventure activities. Star Island is situated along the banks of a private... View all property information
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    $213
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Safe
    • Shared Outdoor Pool...
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    About this property
    Located in Kissimmee Florida! Guard Gated Venetian Bay Community! Featuring two story condominium with three bedroom and two baths. Covered front entry way and neutral exterior paint. Open assigned parking. Ceramic tile and carpet flooring. Floor plan includes great room with living and dining... View all property information
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    $133
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    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    2 bedroom and 2 bathroom Villa at Oakwater Community. Enjoy the Disney Theme parks or go shopping with absolute safety and confidence thanks to the permanent security, so don’t worry about leaving your belongings at the villa. This villa is an excellent choice for a family vacation, it accommodates... View all property information
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    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Fireplace
    • Gym
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    Apartment with 2 Bedrooms 2 Bathrooms with everything to make your stay in Florida a pleasant, master bedroom has a king size bed, the secondary bedroom has a Twin size bed and a bunk above and below Full Twin to comfortably accommodate 6 people the kitchen is fully equipped with cooker, fridge... View all property information
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    Apartment - 
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Gym
    • Hot Tub
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    There is a one time departure cleaning fee on all stays . That cleaning fee is $184 for this property. **Tax not included in nightly rates** heck in time is after 4:00 PM and check out is before 10:00 AM. An early check-in or late check-out can be coordinated for an additional fee. *All properties... View all property information
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    House Rental - 
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Luxurious and spacious 5 bedroom villa with 3.5 bathrooms, completed March 2009. This beautiful 2 storey home is located on an exclusive development with its own enclosed heated swimming pool, which overlooks a conservation area and small lake. The villa is fully equipped to sleep 10 people and is... View all property information
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    $102
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    Villa - 
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Gym
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    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Orlando is the mecca for the family vacation with regards to Theme Parks. So much choice, from Walt Disney World Resort, the Universal Orlando Resort, SeaWorld and Legoland. These destinations helped make Orlando the third most visited city in the USA. Orlando has a warm and humid subtropical... View all property information
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    $88
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    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Gym
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Suitable for children
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    About this property
    Comfortable Family Vacation Rental - Disney area includes Pool WiFi Tennis. Our 3 bedroom, 2 bathroom condo sleeps up to 8 people (not more than 6 adults). It is located at Rainforest Place in Kissimmee, Florida and just a 9 minute drive from the Walt Disney World complex. Have fun in you own... View all property information
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    $140
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    House Rental - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Grill
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    • Washer
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    • Pets allowed
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    About this property
    Welcome to Our 5 Star Luxury Florida Home We welcome you to stay in our luxury Seven Eagles fully air conditioned 3 bed en-suite Town Villa in the 5 Star luxury Reunion Resort and Club in Orlando, Florida. We are just minutes away from the holiday 'World of Entertainment': Disney World... View all property information
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    $115
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    Apartment - 
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Townhouse is located in a gated community / Venetian Bay Villages.Our home is tastefully decorated. It can accommodate up to 8 people and includes luxury amenities such as master bedroom with two person jacuzzi tub.Upstairs is a Junior master bedroom with a Queen bed and full en -suite... View all property information
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    $148
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    Apartment - 
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveller have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Ping Pong Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This luxurious and spacious 1-Bedroom Condo is situated in a large resort and within minutes to Disney World and shopping centers. In the master bedroom is a large jacuzzi, and a comfortable king size bed. The living room features a sofa bed and a dining area for up to 6. The kitchen is features... View all property information
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    A delightful Villa with private pool, 3 bedrooms and 2 bathrooms located at Bellavida Resort. This villa is suitable for an entire family, it can accommodate 6 sleeps and 2 more sleeps on the sofa bed. This unit is fully equipped, with air conditioning, heating, laundry area with washer and dryer... View all property information
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    Apartment - 
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Lake Berkley Resort is a 24 hour security guarded gated community which is located just minutes away to all 4 Disney World Parks , Downtown Disney , Disney Marketplace, Disney Boardwalk Sea World, Universal Studios , Old Town, walking distance to Mid Evil Times Dinner Theater , gas stations,... View all property information
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    House Rental - 
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This is a luxurious villa that has been furnished to an extremely high standard with Smart televisions in the lounge and bedrooms. Modern decor with white leather couches , high standard furniture and an intercom system throughout the villa for communication. A superb pool and spa overlooking the... View all property information
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    Villa - 
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Fantastic, four bedroom, three bathroom villa with private pool and spa, located on beautiful Emerald Island Resort which is a gated community very near to all amenities and less than two miles from Disney. Consists open plan living, two separate dining areas, fully fitted kitchen, pool area has... View all property information
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    House Rental - 
    6 Bedrooms / 14 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Located in a 24 hour manned gated community just ten minutes from Disney World you can feel 100% safe in an ideal location for a Disney Florida Holiday. 6 Bedroom with 1 king 1 queen 2 Double and 2 Twin beds. Each bedroom has its own TV and DVD player. Main living area has plenty of seating and... View all property information
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    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 1
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Cane Island is a luxurious vacation community located less than 4 miles to the magical world of Disney and minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the top golf courses in the country and many are within a 10 minute radius of Cane... View all property information
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    $91
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    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A quiet 1600 square foot bungalow with 3 bedrooms and 2 bathrooms with a nice design for privacy. In-ground pool under a large screened-in patio with a beautiful view. All amenities close to all attractions in area. Two seperate living room/TV areas - children friendly. High speed internet, cable,... View all property information
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    $216
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    Villa - 
    5 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Our luxurious 5 bed, 5 bath tastefully decorated home is perfect for your family vacation. Fully furnished with everything you will need for a comfortable stay - you will never stay in a hotel again! Located on the closed resort to Disney (just 5 minutes away!!!) and 1 minute from the I192 it is... View all property information
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    $255
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    House Rental - 
    6 Bedrooms / 4 Bathrooms / Sleeps 14
    traveller have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    This fabulous 6-bedroom pool home in situated in the 5-star Windsor Hills Resort in Kissimmee. With charming, elegant design and decor, this luxurious home accommodates 12 people in spacious, air conditioned comfort. It is ideal for sharing with your extended family and friends. This villa... View all property information
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    House Rental - 
    6 Bedrooms / 5 Bathrooms / Sleeps 14
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Incredibly beautiful, this 6 bedroom 4.5 bath luxury home features large, screened pool and spa with gorgeous view of a heavily wooded conservation area. Located at the end of a cul-de-sac, this exquisite villa offers peace and privacy. With sparkling granite counter tops and hand chosen custom... View all property information
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    Villa - 
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
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    • Grill
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    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    GRAND OPENING! Brand New Luxurious Water view Castle YEAR 2013 ! The owner has created this home with incredible attention to details. It has an open floor plan with a living-dining great room, and a fully stocked kitchen with high-end stainless steel appliances and marble counter-tops. This home... View all property information
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    $486
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    Villa - 
    7 Bedrooms / 6 Bathrooms / Sleeps 16
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    • Air Conditioning
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    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    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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    House Rental - 
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This luxury 4 bedroom home with a private pool and waterview is located in the beautiful gated golf community of Remmington. Located within 20 mins of all Disney Parks, Universal Studios and the Orlando Airport. Perfectly situated to close by St. Cloud and downtown Kissimmee with many unique... View all property information
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    $140
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    House Rental - 
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    A large beautiful 4 bedroom, 2bath, private pool vacation home. The house is outfitted with everything you need to enjoy your vacation. There is fully well-equipped kitchen which includes a dinette. Appliances include self-cleaning range, microwave, fridge-freezer with icemaker waste disposal... View all property information
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