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89 Holiday homes in Kissimmee

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5 Photos

Villa | 2 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £110 /night

£767 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
It would be hard for you to find a better place at such a price.  …see more

5 Photos

Condo | 3 Bedrooms | sleeps 10

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Enjoy your vacation or business trip in this tastefully decorated 3 bedroom/2 bath /1 car garage condo (2nd floor Gardenia plan) of 1,475 sq feet. Condo consists of one king bed, one queen bed, two twin beds, two queen-size sofa sleepers in the living room, internet acc  …see more

11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Brighton floor plan 1816 sqft.4 bedroom 3 bath home (1 story) South facing pool Welcome to this elegant, professionally decorated Orlando vacation pool home, located in the beautiful Windsor Palms Resort. This home is absolutely perfect for large family groups. T  …see more

Featured properties

7 Photos

Condo | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful professionally decorated condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. This two bedroom two bath condominium offers one king, two twin, and four sofa sized beds. In addition to this, amenities include a full  …see more

7 Photos

House | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Enjoy this beautiful second story 2 bedroom, 2 bathroom condominium on your next vacation. This condo accommodates six comfortably in one king, two twins, and one sofa sized beds, and all of the furniture and appliances are brand new. This condo comes fully equipped wit  …see more

12 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £169 /night

£1177 - £1645 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
4 bedroom 3 bath; Luxury house located 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 bed, TV LCDand master bathroom including a separate shower. 3 othe  …see more

15 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £201 /night

£1405 - £2109 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located in the Windsor Hills Resort. Atte  …see more

15 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Attention to every detail has been put in as we furnished and decorated this home. This 6 bedroom 5 bath 3,275 sq feet unit sleeps 14 in style. With 3 king bedrooms, 1 queen bedroom and 4 twin beds, plus a sleeper sofa, there is plenty of room for everyone to spr  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
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 n  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
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 gate  …see more

13 Photos

Condo | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £70 /night

£490 - £802 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
8105 Coconut Palm Way unit 304, is a bright and airy top floor, two bedroom, two bath, central air conditioned condominium. This condominium is located in the resort community of Windsor Palms – just 2.5 Miles west of Disney. This home features 1 king b  …see more

14 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home with a fantastic view of the lake has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no les  …see more

14 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £177 /night

£1236 - £1814 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Enjoy an amazing vacation in Florida at this lovely home located in the resort community of Windsor Palms. With six bedrooms and three baths, this property can accommodate up to twelve people in comfort, and is perfect for large groups of friends or family. There is a p  …see more

14 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Ideally located ground floor condo with pool and clubhouse just across the street and the outdoor amenities in back. Master bedroom has a queen size bed and a 32" flatscreen TV. There is a private bath off the master. Second bedroom has a queen bed and a 24&  …see more

12 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This 4 bdrm/3 bth home is located in the Windsor Palms. Home has 1 king, 1 queen, 4 twin beds. Home also has many upgrades like tv's in everyroom, dvd, vcr, patio furniture, heatable pool and spa. The Palms clubhouse has a fitness center, movie theatre, and  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £169 /night

£1177 - £1645 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This 4bdrm/3bth house located in a resort style gated community of Windsor Palms offfers 2 king, 1 queen and 2 twin beds. This home has free long distance and has tv's in everyroom. The home also has a private pool and spa. This home sleeps up to 10 persons  …see more

12 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £157 /night

£1093 - £1687 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
2317 sq ft 5 bedroom 3 bath (2 story) Pool home. We invite you to enjoyyour next vacation at our luxurious, brand new and beautifully decorated 5bed/3 bath Home with 28ft pool. Sleeping accommodation features one elegantmaster suite with 1 king size bed; 2 rooms  …see more

22 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Absolutely perfect for the large family groups or smaller groups just looking for a roomier more comfortable house. This spacious 3275 sq. ft. home has 2 master suites each offering king size beds and 40" TVs. Another bedroom on the main floor has a king siz  …see more

15 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £179 /night

£1249 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Relax in this elegant and professionally decorated 5 bedroom/5 bath pool home, located in the beautiful 5 Star, gated community of Windsor Hills, in Kissimmee, Florida --“Kissimmee Castle." This home has been completely renovated and newly furnishe  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Newly Renovated 5 bedroom, 5 bath property in the 5star gated Windsor Hills community just 5 minutes from Walt Disney World and the surrounding attractions. After an energetic day exploring the sights and sounds of this magical playground you can return home to y  …see more

14 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located on a beautiful lot overlooking a pond.see more

23 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £204 /night

£1422 - £2109 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautifully decorated 6 bedroom 3.5 bath 2 story home located in the Windsor Palms Gated Private Community just minutes from Disney comes fully equipped for a group of up to 12 people. Home has 2 king, 1 queen, 4 twin, 1 bunk bed, 1 futon and 1 pull out couc  …see more

6 Photos

Condo | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £70 /night

£490 - £802 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Enjoy this 2 Bedroom, 2 Bath vacation condominium that will sleep 6 comfortably. Sleeping arrangements include 1 king, 2 twin, and 1 sofa sized beds. This property also comes with a fully equipped kitchen inclusive of ice maker, coffee maker, microwave, and dishwasher.  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £80 /night

£557 - £928 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Welcome to this elegant, professionally decorated Orlando vacation condo, located in the beautiful Windsor Palms Resort. This property features all the comforts of home, and more! Windsor Palms is a gorgeous gated community, just minutes from the gates of Walt Di  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Located in Windsor Hills, this beautiful home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms, five baths, and a 2  …see more

10 Photos

House | 5 Bedrooms | sleeps 11

2 Nights min stay

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from £180 /night

£1257 - £1940 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
We invite you to enjoy this home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located in the Windsor Palms Resort. Att  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Luxury condo with an idyllic setting – this is one of the few residences in Windsor Hills with a direct lake view – you can enjoy watching the sunset over the lake from the balcony. Professionally decorated, the interior is luxurious with top  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Welcome to this beautiful Florida vacation condo in Oakwater which was built in 2007. This 3 bedroom, 2 bath condo sleeps 8 and was completely refurnished with new furniture in November 2009. New laminate flooring were installed in the bedrooms in November of 2011. Ther  …see more

7 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This very modern 6 bedroom 4 bathroom home has been professionally furnished and decorated including beautiful relaxing colors through-out the home with custom window treatments. No expense has been spared with this home which comes with every little item to make  …see more

10 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £147 /night

£1025 - £1434 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This Lovely 4 bedroom/3 bath home is located in gated Windsor Palms just minutes to Disney. The home features a private swimming pool and spa/jacuzzi with pool heating features. It also includes a home entertainment DVD combination, play station and TV's in  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
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 r  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
We invite you to enjoy our condo 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 1st floor condo in the Windsor Hills Resort. Attention to every  …see more

16 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £205 /night

£1434 - £2151 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Located in Windsor Hills, this beautiful, two-story home has been furnished and decorated with the utmost attention to every detail so that you can enjoy the luxury of a great vacation rental as well as the comforts of home. With no less than five bedrooms, a game room  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
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 beautiful lak  …see more

17 Photos

House | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £231 /night

£1616 - £2404 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This 6 bedroom 4 bath 2,812 sq feet unit sleeps 12 in style. With 2 king bedrooms, 1 queen bedroom, 1 double 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 and stay in. The dinning room o  …see more

10 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This vacation condominium will comfortably sleep 6 with 1 King-size and 4 Single beds. Each bedroom has a TV with VCR/DVD player. The amenities of this condo include access to off-street parking, a hot tub, pool, and tennis courts. Also, the cheerful Galley kitchen is f  …see more

6 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £87 /night

£604 - £970 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This is a new 1st floor condo in beautiful Windsor Hills, where there is privacy near the end of the building.It is decorated with the premium Catalina package. The home comes with wireless internet, a playstation II, 2 DVD players. There is a 32" TV in the living  …see more

17 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £180 /night

£1257 - £1940 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Welcome to this beautifully furnished home in Kissimmee, Florida. With five bedrooms and three-and-a-half baths, it can accommodate up to ten people easily and features both a private patio and swimming pool. The full kitchen provides you with everything you need to whi  …see more

9 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £84 /night

£582 - £886 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Water and nature views surround this spectacular 3 bedroom 2 bath, 1500 sq.ft. newly furnished and professionally decorated condo. Our Home offers WiFi as well as unlimited local and long distance to more than 60 countries(some restrictions apply), so you can eas  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £180 /night

£1257 - £1940 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Floor Plan (The Barrington II) 2,806 sq. ft. 2 story home with pool (West Facing Pool). 5 bedroom 3.5 bath; Luxury house located beautiful gated community just 2.5 miles(4km) from the gates of Walt Disney. The house was recently renovated and well decorated. Mast  …see more

11 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful 3 bedroom/ 2.5 bath condo is located in the brand new gated community of Oakwater. Condo consists of one king bed, one queen bed, two twin beds, game cube, Internet access, patio, and fully equipped kitchen. Unit can accommodate up to 6 people comfortably  …see more

9 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful 3 bedroom/ 2.5 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts and basketball courts. Condo consists of one kin  …see more

10 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Thank you for taking the time to look at our Florida vacation home. For your comfort and enjoyment, we are proud to offer you our town home which features brand new furniture and equipment which was bought in March 2012 which can accommodate up to 8 people. Avail  …see more

13 Photos

House | 6 Bedrooms | sleeps 8

2 Nights min stay

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from £177 /night

£1236 - £1814 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Attention to every detail has been put in as we furnished and decorated this home. This 6 bedroom 4 bath 3,073 sq feet unit sleeps 13 in style. With 2 king bedrooms, 1 queen bedroom, and 4 twin beds, there is plenty of room for everyone to spread out and relax af  …see more

17 Photos

House | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £195 /night

£1363 - £1982 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
A stylish, warm and homely welcome awaits you in our 7 Bedroom true-luxury 2,827sq.ft holiday villa, complete with extended west facing private heated swimming pool, Jacuzzi and a fully fitted air-conditioned Games Room. Our home can accommodate up to 14 people m  …see more

7 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful and professionally decorated condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney World. This two bedroom condominium sleeps four and offers one king sized bed and two twin sized beds. Along with two baths, full kit  …see more

11 Photos

Condo | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
A beautiful spacious condo located in a new-gated community. This 3 bedroom, 2.5 bathrooms, Full Kitchen and Dinning is only a half-mile from Disney. It has a large Clubhouse with a Gym, Pool and Spa, Children's Splash Area, Basketball and Volleyball Court.  …see more

14 Photos

Villa | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £192 /night

£1341 - £1856 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Villa La Dolce Vita is new 4 bedroom/4 bathroom Luxury Home that sleeps up to 10 people. Our villa is located in the new five star ***** Windsor Hills Reserve Gated Community, the newest, most luxurious and closest private home resort community to Walt Disney Wor  …see more

10 Photos

Condo | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £99 /night

£688 - £1055 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Enjoy this brand-new resort featuring luxury condominiums! This beautiful gated community is just 1.5 miles (2.5km) from the gates of Walt Disney World. At Oakwater, you're sure to find accommodations to suit your vacation needs. The residences range in size  …see more

5 Photos

Condo | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £74 /night

£515 - £760 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This beautiful 2 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. This property sleeps 6 comfortably in 1 queen, 2 twin, and 1 sofa sized beds. Also, for your convenience, this property includes a full sized k  …see more

Orlando Kissimmee is a great location for a family holiday, with easy access to Florida's big attractions - Disney World, Busch Gardens and Universal Studios. There are also rides through the Florida Everglades and plenty of children-friendly activities to keep everyone happy. The area has some excellent beaches, amongst them Clearwater Beach and Daytona Beach.