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Holiday Rentals in Kissimmee, FL

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$1,424
Per Week
1 / 11
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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$178
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$408
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1 / 14
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6 Bedrooms, 4 Bathrooms, Sleeps 14
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$470
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1 / 15
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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About this property
Floor Plan (Brentwood) 2,812 sq. ft. 2 story home with pool and spa (North-East facing pool) A luxury, waterfront, executive 'dream home' on the prestigious Windsor Hills gated resort just 10 minutes from Disney. Professionally interior designer furnished and decorated to the highest level with... View all property information
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$363
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1 / 13
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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  • Suitable for children
  • x
  • x
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  • Elder access
  • x
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About this property
We are proud to offer this elegant 5 bedroom, 5 bathroom vacation villa in Windsor Hills. This home is tastefully painted throughout and features leather furniture in the living room. There are bunk beds for the kids along with a set of twin beds in the Mickey bedroom. The games room includes a... View all property information
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$262
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3 Bedrooms, Sleeps 6
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$363
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1 / 15
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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  • Internet Access
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  • Suitable for children
  • x
  • x
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  • x
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About this property
Floor Plan (The Seville) 2,827 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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From
$240
Per Night
1 / 10
3 Bedrooms, Sleeps 8
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$110
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1 / 20
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Shared Outdoor Pool...
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  • x
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  • ?
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About this property
Luxury Vacation Home in Kissimmee, Florida Chatham Lakes Villa is a beautiful 3 bedroom 2 bathroom villa, situated in the quiet friendly neighborhood of Chatham - an outstanding development within 5 miles of Disney World. It is in easy reach of all other major attractions. So close, that the... View all property information
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$3,817
Per Week
1 / 30
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Private Pool
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • ?
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  • Elder access
  • ?
About this property
This home is of the courtyard style but with the difference of having the pool and deck area located at the rear of the home with additional outdoor dining and seating in the homes centre courtyard There is a queen size bedroom suite separated from the main house by the courtyard which offers it s... View all property information
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From
$3,096
Per Week
1 / 21
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Private Pool
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  • Pets allowed
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  • Suitable for children
  • ?
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  • Elder access
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About this property
Simply The Best 3 Bedroom Reunion Resort Home Available A beautiful custom built 3 bedroom home commanding an enviable position overlooking one of the three PGA golf courses that the Reunion Resort offers Arnold Palmer Tom Watson and Jack Nicklaus The large pool and deck area is probably one of the... View all property information
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$2,735
Per Week
1 / 13
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Internet Access
  • Private Pool
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Elder access
  • ?
About this property
Tastefully furnished throughout this stunning villa includes all the appliances expected in a modern family home that will make your stay much more comfortable With two living areas there is ample space to please all your family High speed wireless internet access Baby must haves include a high... View all property information
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$2,968
Per Week
1 / 10
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
  • Safe
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • Elder access
  • ?
About this property
This fantastic home is a lavishly furnished 5beds 5baths villa with all your vacation needs and less than 1 5 miles from the gates of Walt Disney World with Sea World and Universal Studios nearby 3 Themed Rooms Mickey Room Princess Room LEGO Room Our villa features the very best in Electronic... View all property information
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$178
Per Night
1 / 47
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3 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
Harmonious house with 3 bedrooms and 2 full baths and 1 half bath, with full kitchen and laundry room. It has one bedroom with queen bed, 1 bedroom with 2 single beds and 1 bedroom with 2 single bunks, and it can accommodate up to 8 people comfortably! The house offers an entertainment area with... View all property information
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From
$408
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1 / 19
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6 Bedrooms, 3 Bathrooms, Sleeps 14
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  • Internet Access
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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... View all property information
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From
$240
Per Night
1 / 10
3 Bedrooms, Sleeps 6
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From
$262
Per Night
1 / 11
3 Bedrooms, Sleeps 8
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From
$262
Per Night
1 / 12
3 Bedrooms, Sleeps 8
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From
$262
Per Night
1 / 10
3 Bedrooms, Sleeps 8
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From
$2,557
Per Week
1 / 20
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
  • Safe
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
beautiful six bedroom four bathroom villa home in the brand new guarded gated resort community of Windsor Hills Just 2 miles from the main gate of Walt Disney World this spacious 2812 sq ft house has been decorated and furnished with special TLC to ensure a high level of comfort and quality Welcome... View all property information
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From
$5,929
Per Week
1 / 27
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This fabulous home has just been completely refurbished to a high standard of contemporary furnishings and decor with the addition of several amenities to ensure this home meets all your requirements The entertainment room offers pool table an over sized wall mounted flat screen theatre seating and... View all property information
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From
$3,636
Per Week
1 / 30
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Private Pool
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Waterpark and Golf not included in rental rate Outstanding custom built home on three storeys offers abundence of space for family gatherings our beautiful unique custom built home has two parts The first being the three story main house On the ground floor is the living area which incorporates a... View all property information
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From
$391
Per Night
1 / 13
5 Bedrooms, Sleeps 10
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From
$3,501
Per Week
1 / 25
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Elder access
  • ?
About this property
Executive Private Villa With Huge Pool The Very Best Location Minutes To All The Disney Attractions In A Safe Gated Community On Formosa Sleeps 12 comfortably Formosa Garden Estates has long been recognized as one of the most prestigious vacation communities in Central Florida This fantastic home... View all property information
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From
$146
Per Night
1 / 14
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This beautiful home located in the Crescent Lakes community offers you the following:2 Queen Master SuitesGarden Tub in One of the Master Baths1 Double Bedroom1 Twin Room w/Two Twin BedsFlat Screen TVs in Two of The BedroomsTwo Living Areas both with Flat Screen TelevisionsCable TelevisionComputer... View all property information
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From
$4,985
Per Week
1 / 30
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Stunning Custom Built Reunion Resort Pool Home 4 Bedroom Our 5 Star 4 Bedroom Villa in Reunion Resort Orlando Florida A stunning custom built home new to the vacation rental market As expected from a home located on the Legends Corner division of the Reunion Resort this home is extremely spacious... View all property information
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From
$2,833
Per Week
1 / 24
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7 Bedrooms, 6 Bathrooms, Sleeps 16
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Luxuriously furnished with a abundance of arts and artifacts this is a truly special villa With seven bedrooms and six bathrooms this villa can accommodate fourteen guests in comfort without feeling crowded the abundance of living space stretching across two lounge areas a games room private pool... View all property information
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From
$3,366
Per Week
1 / 20
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This Is The Ultimate 5 STAR Resort Villa And Location Visit our luxury 5 bedroom 5 Bathroom detached villa with Privat Pool and Spa overlooks a conservation pond area top of the range appliances and elegant decor Whether it s sun drenched lazy days or fun packed theme park adventures from the... View all property information
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From
$2,557
Per Week
1 / 18
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6 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
6 Bedroom 3 5 Bathroom Luxury Retreat This beautiful villa locates in the New Crystal Cove a beautiful gated community This villa has 6 bedrooms 3 5 bathrooms and heated private pool comfortably sleeps up to 12 guests perfect for large group staying together Our private pool home is the perfect... View all property information
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From
$259
Per Night
1 / 15
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Exceptionally stunning and professionally furnished by local Interior designer our private town home is located in the prestigious 5 Star gated community of Paradise Palms Resorts, voted one of Orlando's most beautiful destinations. Brand New for 2013, 2 story town home with 4 bedroom 3 bath 1,914... View all property information
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From
$200
Per Night
1 / 7
2 Bedrooms, Sleeps 6
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From
$181
Per Night
1 / 10
3 Bedrooms, Sleeps 6
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From
$4,114
Per Week
1 / 27
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6 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful 6 Bedroom courtyard style home is located on Golden Bear Drive in the Legends Corner of the world renowned Reunion Resort The decor and furnishings have been selected to create a modern yet comfortable environment for you to experience that home from home feel during your vacation This... View all property information
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From
$5,363
Per Week
1 / 27
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5 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
If you are looking for luxury and comfort during your vacation then this is the home for you Having an enviable position within the Reunion Resort and Spa overlooking the Jack Nicklaus Golf Course on the westside of Reunion in Legends Corner This fabulous home can offer both formal entertaining or... View all property information
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From
$275
Per Night
1 / 14
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
We are pleased to offer our beautiful privately-owned 4 bedroom 3 bath 1835 square foot Located only 2.5 miles from Disney, in the peaceful community of Windsor Palms - a small, quiet, much sought after gated community with onsite 24/7 security. Our home has a private screened-in pool, WITH ATAND... View all property information
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From
$509
Per Night
1 / 18
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Dishwasher
  • Hot Tub
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Welcome to this gorgeous 6 bedroom, 5 bathroom rental home in the stunning resort community of Paradise Palms. The fully equipped kitchen features stainless steel appliances, granite counter tops and upgraded tile and cabinetry. For your dining experiences, there is plenty of seating at the large... View all property information
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From
$367
Per Night
1 / 18
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Brentwood floor plan - 3534 sq.ft. 2 story West facing pool Welcome to our beautiful new home situated in the of Windsor Hills,the closest resort community to Disney World! Our luxury 6 bedroom, 4 bathroom smoke-free home features two master suites and two living rooms. 6 bedroom 4 bath West... View all property information
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From
$482
Per Night
1 / 20
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This Is The Ultimate 5 STAR Resort, Villa And Location Visit our luxury 5 bedroom 5 Bathroom detached villa with Privat Pool and Spa overlooks a conservation/ pond area. top of the range appliances and elegant decor, Whether it's sun drenched lazy days or fun packed theme park adventures, from... View all property information
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From
$123
Per Night
1 / 36
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Walt Disney World® Resort worked with the top vacation rental home companies in central Florida to design a program that would give guests a simple way to easily see if the company that they were booking with was safe, customer focused and consistently provides great service to its guests. Wherever... View all property information
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From
$592
Per Night
1 / 19
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
6 bedroom 5 bath 3,275 sq feet home with 5 Star Resort amenities In Orlando close to Disney World. Our home is Elegantly and professionally furnished, with all the comforts of a home. with 6 bedroom 5 bath sleeps 12 in style. With 2 king bedrooms and 4 queen bedrooms, there is plenty of room for... View all property information
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From
$296
Per Night
1 / 14
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Minutes from Mickey Luxury 4 Bedroom 3 Bathroom with Private Pool and Spa Our spacious villa is big enough to accommodate up to 8 people. We can offer you a very well equipped home away from home so you can relax and enjoy your break in the Florida sunshine. The villa is fully equipped with bed... View all property information
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From
$455
Per Night
1 / 17
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
OUR HOME AWAITS YOU...SOUTH FACING POOL & SPA We invite you to stay at our 4 bedroom 4 bathroom excutive villa elegantly furnished to high standard. We are perfectly situated just 1.5 miles to Disney, Attention to every detail has been put in as we furnished and decorated this home. This 4 bedroom... View all property information
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$296
Per Night
1 / 12
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This home is absolutely perfect for large family groups. This property features all the comforts of home, with 4 Bedrooms and 3 Bathrooms with 2 En Suites and more! There is a 42 inch LCD TV in the Living Room along with a 32 inch LCD TV in the Master Bedroom with DVD player. The pool was also... View all property information
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From
$427
Per Night
1 / 19
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • x
About this property
This 3097 sq ft two story 5 bedroom villa is located just minutes from Disney located at Reunion Resort. Featuring a beautiful screened inground South facing pool with covered lanai. This large patio will provide you an your family such a relaxing vacation to Florida Attention to every detail... View all property information
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From
$259
Per Night
1 / 20
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5 Bedrooms, 5 Bathrooms, Sleeps 11
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Situated on the lovely Watersong gated Community, 15 mins from Disney and just 30 mins from Orlando Airport, our luxurious 5 bedroom, 4.5 bathroom villa is available for your dream holiday. You will be within minutes of all the essential amenities such as supermarkets, banks and gas/petrol... View all property information
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From
$294
Per Night
1 / 13
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 4 Bedroom 3 Bathroom Pool Home in 5* Resort Community, 3 Miles to Disney Our privately owned pool home is situated on the prestigious 5 Windsor Palms Resort, landlines, Free Wi-Fi free use of the prestigious 5* Windsor Palms resort facilities during your stay including communal pool, spa,... View all property information
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From
$207
Per Night
1 / 24
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5 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • 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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From
$16,794
Per Week
1 / 20
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9 Bedrooms, 10 Bathrooms, Sleeps 18
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Pool
  • Safe
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
SIMPLY THE BEST NO QUESTION This is the largest rental home in Orlando Ignore what others state this is the house with a Combined area of over 14 000 sq ft Completed in 2012 to the most exacting standards If you want luxury this is the house Within reunion others make claims This is the largest... View all property information
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From
$294
Per Night
1 / 20
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
STUNNING NEW DESIGNER 5 BEDROOM TOWNHOUSE WITH SPLASH POOL!! For the most discriminating traveller who desires the best in vacation accommodation. First class 5-star Townhouse of over 2,128 sq ft Absolutely perfect for family groups, our vacation rental in Orlando features all the comforts of... View all property information
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From
$367
Per Night
1 / 18
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This beautiful 6bed /3.5 bath home is situated on Windsor hills resort which is the number one resort in Florida! The home I only minutes from the Disney gates! large south-west facing pool & spa (lots of sun!) Living area The living area has one 3 seat sofa, one 2 seat sofa and a comfort... View all property information
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