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Holiday Rentals in Kissimmee, FL

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$453
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1 / 21
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6 Bedrooms, 5 Bathrooms, Sleeps 14
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$502
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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$234
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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$188
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
Comfortable house in Bella Vida Resort! The home offers 3 bedrooms, 2 baths and 1 half bath, plus full kitchen, living room, Wi-Fi, cable TV, laundry, bedding and bath area with barbecue and private pool. The accommodations are 1 master suite with queen bed and 2 bedrooms with twin beds, and can... View all property information
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$170
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1 / 15
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
This house is perfect for your stay! It has 3 bedrooms and 2 bathrooms: 2 bedrooms with a king size bed and 1 bedroom with two single beds, and can accommodate up to 6 people comfortably. The house offers a full kitchen, living room and dining room, laundry, bedding and bath, cable TV, Wi-Fi... View all property information
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$349
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5 Bedrooms, 8 Bathrooms, Sleeps 10
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  • Internet Access
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  • x
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About this property
Floor Plan (The Barrington II) 2,176 sq. ft. 2 story home with pool (West Facing Pool) 5 bedroom 3.5 bath; Luxury house located in a beautiful gated community just 2.5 miles(4km) from the gates of Walt Disney. The house was recently renovated and well decorated. Master suite with king size... View all property information
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$226
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1 / 21
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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About this property
We are pleased to offer our beautiful privately-owned 4 bedroom 3 bath home just two stoplights from Disney. Our spacious home is situated in the beautiful community of Windsor Palms which is a small quite, gated community with onsite security 24/7. Our home has a private screened-in pool, hot tub,... View all property information
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$318
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1 / 18
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • Elder access
  • x
About this property
We invite you to enjoy our stunning vacation home. Absolutely perfect for 2 families, our home features all the comforts of home and more! make our home your home. Attention to every detail has been put in as we furnished and decorated this home. This 5 bedroom 5 bath 2,966 sq feet unit sleeps 10... View all property information
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$496
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1 / 19
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Pets allowed
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  • Suitable for children
  • x
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  • x
About this property
Executive WATERFRONT villa. Extra privacy with no rear neighbors overlooking the pool/spa area. Furnished by a professional interior design firm along with custom made furniture. 6 bedrooms: 2 kings, 2 queens, and 2 sets of twins. BEST location in Windsor Hills with only couple minutes walking... View all property information
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$197
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1 / 18
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Dryer
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
***FREE WIRELESS INTERNET JUST BRING YOUR LAPTOP*** ***GREAT GAMES ROOM & equipment***Free Tennis courts... Enjoy our lovely, furnished home with a private heated pool and screened lanai on a sunny corner lot in the safe gated community of Emerald Island Resort. This Non-Smoking home has four... View all property information
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$170
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1 / 12
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • x
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About this property
This gorgeous house has décor inspired by the Harry Potter movies. It has 3 bedrooms and 2 baths with full kitchen, living room, laundry room, cable TV, Wi-Fi internet and telephone. The accommodations are: 1 bedroom with a King Size bed and 2 bedrooms with two single beds. (Sleep up to 6 people... View all property information
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$311
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1 / 25
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Pets allowed
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About this property
6BR/3.5BA Windsor Hills Resort private pool home, 1.5 mile to Disney World Orlando, sleeps 12-14!! (plus 2 infants in pack n plays provided, no charge). Wireless High speed internet, private pool, spa, game room and much more! Save money and enjoy luxury comforts of home right at Mickey's doorstep!... View all property information
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$347
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1 / 11
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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  • Hot Tub
  • Internet Access
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Floor Plan (The Spencer) 2,382 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... View all property information
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$129
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1 / 24
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • ?
  • ?
About this property
This vacation home is equipped with all you will need for a relaxing and enjoyable vacation with cable TV, fully equipped kitchen, washer/dryer. Master bedroom has a king size bed, second bedroom has queen size bed, and third bedroom has two twin. Its located just about 10-15 minutes from Walt... View all property information
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$170
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1 / 37
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
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  • Suitable for children
  • x
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  • Elder access
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About this property
Beautiful and comfortable house with 3 bedrooms, 2 bathrooms and balcony. This house is perfectly decorated and equipped with everything you need to have an unforgettable vacation! It offers 1 bedroom with King bed and 2 bedrooms with queen bed, full kitchen, dining area and living room, Wi-Fi... View all property information
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$170
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
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  • Suitable for children
  • x
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  • Elder access
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About this property
Excellent choice for your vacation with 3 bedrooms and 2 bathrooms: 2 bedrooms with a King size bed and one bedroom with two single beds, and can accommodate up to 6 people comfortably! The house has a full kitchen, living room and dining room, laundry, bedding and bath, cable TV, WiFi internet... View all property information
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$234
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1 / 9
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • Elder access
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About this property
Relax by your private pool with your favorite cocktail or join in at the fantastic resort pool and spa. For those with energy to spare, work out in the well equipped fitness center or have fun on the basketball and volleyball courts. This brand new, clean, well maintained and beautifully decorated... View all property information
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$331
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1 / 20
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6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Look no further if you are searching for the perfect vacation home! This is the one! This superb home has just been completed in September 2013 and all furnishings and fittings are all brand new and of high quality. The villa owners have done an exceptional job of styling and upgrading the home... View all property information
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$373
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1 / 19
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Pets allowed
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  • Suitable for children
  • x
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  • Elder access
  • x
  • x
About this property
FANTASTIC 4 BED GOLF FRONT HOME WITH SEPARATE 1 BEDROOM APARTMENT Reunion Resort is a short drive from Disney World Orlando and is set amongst 3 picturesque signature golf courses by Tom Watson, Arnold Palmer, and Jack Nicklaus with miles of biking trails and scenic walking. Yes this is another... View all property information
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$301
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1 / 20
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6 Bedrooms, 6 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Dryer
  • Internet Access
  • Private Outdoor...
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
tespool it is. The 10' x 40' covered Lanai area with outdoor fans, allows full protection from the sun or elements while you relax on lounge chairs or have a relaxing meal. The 30' x 40' deck is fully enclosed with screening. The 16' x 32', built in, heated, tiled pool and separately heated Hot Tub... View all property information
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From
$462
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1 / 13
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6 Bedrooms, Sleeps 12
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Amenities & Details
  • Pool Table
  • Private Pool
  • Wi-Fi
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Check-In: 3:00 PM Check-Out: 10:00 AM View all property information
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From
$355
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1 / 17
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Pets allowed
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  • Suitable for children
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  • x
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About this property
*Waterpark and Golf not included in rental rate. Our stunning four bedroomed house, situated in an elevated position has far reaching views across the Palmer and Watson golf course. The master en-suite king bedroom opens out onto the balcony where you can enjoy the distant nightly fireworks.... View all property information
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$374
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1 / 13
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5 Bedrooms, Sleeps 10
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Amenities & Details
  • High Speed Internet
  • Internet Access
  • Pool
  • Pool Table
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Check-In: 3:00 PM Check-Out: 10:00 AM View all property information
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From
$84
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1 / 23
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Studio, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Hot Tub
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
Located in the heart of Central Florida, Park Inn by Radisson Resort & Conference Center offers all of the best of work and play for families and travelers looking to maximize their fun and their budget. Our Kissimmee resort offers spacious, comfortable accommodations alongside flexible conference... View all property information
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From
$170
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1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This house is fantastic for your vacation! It has 3 bedrooms and 2 full baths: 1 bedroom with a King size bed, 1 bedroom with a queen bed and 1 bedroom with two single beds, and can accommodate up to 6 people comfortably. The house offers open concept with full kitchen, living room and dining... View all property information
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From
$433
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1 / 22
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
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About this property
Make this large vacation villa your haven whilst enjoying the pleasures of the famous attractions in Orlando Florida on your next travel. With 6 bedrooms, 4 bathrooms and high standard facilities, this home has comfortable and convenient accommodation of up to a traveling group of 12. You can find... View all property information
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$149
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1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • Elder access
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About this property
Vista Cay is a luxurious resort with beautiful amenities: 2 community swimming pools, fitness room, putting green and much more. This beautiful 3 bedroom and 2 bathroom condo is fully furnished, that easily will accommodate your family of up to 8 persons. This condo allows everyone to have a... View all property information
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$135
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1 / 51
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Osprey Villa is a Disney vacation villa that is located in the quiet community of Indian Creek. This villa has been newly renovated and is the perfect place to have a relaxing vacation. Our villa offers all the comforts of home… Whether you are looking to relax by the pool or enjoy all of... View all property information
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From
$281
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6 Bedrooms, 5 Bathrooms, Sleeps 12
Booking
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  • Suitable for children
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About this property
This six bedroom, four and half bathroom pool home is the perfect place to enjoy a family vacation in sunny Florida. Curious about additional information? Maybe this will help! General: * Cable television in the living room and each bedroom. * Wireless High Speed Internet - FREE of charge! * Air... View all property information
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From
$257
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1 / 15
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Pets allowed
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  • Suitable for children
  • x
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About this property
This 4 bedroom, 3 bathroom home located in Champions Gate has all the comforts of home and more. This beautiful rental home has a stunning brick facade and stylish tile roof. Once inside, the exquisite leather furniture package and professional decor will help ensure you have the vacation of a... View all property information
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$317
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1 / 25
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • Elder access
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About this property
Beautifully furnished and decorated 5 Bedroom 5 bathroom vacation home with private screened in Pool and spa heated upon request with extra charge. Back yard faces west with sun in afternoon and evening. This home features 3 master suites with king size beds and 2 bedrooms with 2 twin beds each.... View all property information
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$175
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1 / 8
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
This spacious five bedroom home is located at Seasons, off of Highway 192 in Kissimmee and just 15 Minutes from Walt Disney World Resort. A blend of carpet, cool ceramic tile, and leather furnishings create a luxurious, relaxing ambience. The property offers open plan living and bedrooms on both... View all property information
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$122
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1 / 15
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
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... View all property information
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$223
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1 / 28
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Attention to every detail has been put in as we furnished and decorated this townhome. This 4 bedroom 3 bath 1,914 sq feet unit sleeps 8 in style. With 1 king bedroom, 1 queen bedroom and 2 twin bedrooms, there is plenty of room for everyone to spread out and relax after a day out or to just relax... View all property information
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$422
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1 / 14
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7 Bedrooms, 6 Bathrooms, Sleeps 16
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Elder access
  • x
About this property
Absolutely stunning! Welcome to Our Villa, a 7 bedroom 6 bathroom dream. Comfortably sleeping up to 16 + cot. The location is perfect, a few minutes from the bustling 192, with it‘s abundance of restaurants, shops, supermarkets and attractions, also just 2 miles from Disney’s doorstep and within... View all property information
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$206
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1 / 9
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3 Bedrooms, Sleeps 6
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  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Elder access
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About this property
Check-In: 3:00 PM Check-Out: 10:00 AM View all property information
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From
$117
Per Night
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1 / 16
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
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About this property
This amenities include...4 bedrooms (can sleep 10 people),3 full bathrooms, Large private pool and screened deck ,Fully equipped kitchen with complete set of cooking and dining utensils,Free WiFi and cable TV,Free phone calls within the US and Canada Lake Berkley is a Gated community with 27/4... View all property information
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$449
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6 Bedrooms, 4 Bathrooms, Sleeps 14
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  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Floor Plan (Brentwood) 2,812 sq. ft 2 story home with pool and spa (North-East facing pool) This executive vacation home located in the gated community of Windsor Hills Resort (10 minutes from Disney) is a luxury waterfront property with a private lake side view from the pool and spa area.... View all property information
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$567
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1 / 19
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
WHEN ONLY THE BEST WILL DO!! with More Than 3000 sq ft., Offers Every Comfort That You Would Expect From A 5 Star Resort. Executive Waterfront 6 bedroom 4 bath (2 story) our newly appointed executive vacation home is located at the 5 Star gated community of Windsor Hills Resort just 5 minutes... View all property information
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$204
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Create memorable moments with your family! Gorgeous 4 bedroom / 3 bath home in the gated Emerald Island Resort. This home sleeps a maximum of 10 people and includes 2 master ensuites so adults can truly enjoy the privacy of their own bedroom and bath. Our home has a private screened in pool and... View all property information
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From
$318
Per Night
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1 / 10
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Pets allowed
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  • Suitable for children
  • x
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About this property
5* Plus....The Retreat at Champions Gate...Resort Brand New Vacation Home Jan 2014 only 12 minutes drive from the gates of Disney. A perfect for a home away from home. There is 32" TV's and cable TV in all rooms. Wireless internet access is provided so you can stay in touch with home. The villa... View all property information
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From
$381
Per Night
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1 / 19
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Hot Tub
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Windsor Hills Spencer ll - 2382 sq. ft. Welcome to this elegant, and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. Absolutely perfect for large family groups, this property features all the comforts of home and more! Windsor Hills is a gorgeous... View all property information
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From
$165
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1 / 9
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4 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Heated Pool
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Dwarfs Den is a 4 bedroom, 3 bathroom Orlando vacation townhome that sleeps 7 located in the beautiful community of The Villas of Seven Dwarfs. The bedrooms consist of a Queen master bedroom with full en-suite facilities, a second Master bedroom with Queen bed and full en-suite facilities, and... View all property information
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$347
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
Windsor Hills Spencer ll - 2382 sq. ft. Welcome to this elegant, and professionally decorated Orlando vacation pool home, located in the beautiful Windsor Hills Resort. Absolutely perfect for large family groups, this property features all the comforts of home and more! Windsor Hills is a... View all property information
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
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About this property
Our Value vacation rental selection is your best choice of vacation homes in Orlando for your family vacation. You will find all of the standard amenities that come with a private pool home. It is important for our guests to know that all our Value vacation rentals are cost efficient option because... View all property information
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From
$217
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4 Bedrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • ?
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  • Wheelchair access
  • Elder access
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  • ?
About this property
Check-In: 3:00 PM Check-Out: 10:00 AM View all property information
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From
$141
Per Night
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1 / 6
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • 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
If it’s relaxed living and plush surroundings you’re looking for, then this villa has it all. A warm welcome to our luxurious home where we hope that you will enjoy the perfect vacation! Our open plan villa was designed with your relaxation in mind. This villa is a truly splendid home from which to... View all property information
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From
$433
Per Night
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7 Bedrooms, 5 Bathrooms, Sleeps 14
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
You are SPECIAL and deserve a SPECIAL home.The Retreat is a brand new luxury 7 Bedroom 5 bathroom villa situated 12 minutes from the magic Disneyworld in the new exclusive Champions Gate Resort. Coming Soon...As our guest you will have access to the many extra facilities available at Champions Gate... View all property information
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From
$128
Per Night
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1 / 17
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Pool
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Hello! We are a company recognized for providing high quality services which operates in all segments of tourism providing lodging, airfare, health insurance, transfers, and all you need to make an unforgettable trip! Located in Kissimmee, in Crestwynd Bay community. This house has 3 bedrooms, 3... View all property information
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From
$379
Per Night
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1 / 32
Payment Protection
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
T his villa is situated in the exclusive resort of Reunion, only 6 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa has every luxury with A SOUTH FACING PRIVATE POOL , Spa and a 42" flat screen TV in the living room. The resort itself is second to none,... View all property information
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Suitability

  • Wheelchair access (594)
  • Elder access (1,570)
  • Suitable for children (2,088)
  • Pet friendly (197)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (2,770)
  • Internet (2,708)
  • All pools (2,248)
  • Washer/Dryer (1,820)
  • Other outdoor space (1,819)
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