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586 Holiday homes in Kissimmee

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586 Results  |  
16 Photos

Condo | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £66 /night

£461 - £520 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Our House near the Mouse Superb, Spacious Condo only 4 miles from Disney on the Lindfields Estate.Superb Golf Courses, restaurants and shops all nearby  …see more

21 Photos

Condo | 3 Bedrooms | sleeps 8

Excellent 5/5 

5 Nights min stay

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from £86 /night

£601 - £928 / week

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Key info:

  • Nearest beach 123 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This family friendly home is minutes from Disney and all Orlando attractions. Whether planning a dream family vacation or break away with friends, you'll have everything you need for a perfect vacation right here at this luxury Reunion Resort property. Luxurious & spacious Reunion Resort condo, perfect for your family to enjoy a dream Orlando/Disney vacation.  …see more

24 Photos

House | 6 Bedrooms | sleeps 12

Excellent 5/5 

5 Nights min stay

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from £121 /night

£847 - £1395 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This beautifully furnished, air-conditioned executive home is at Emerald Island Resort, the nearest gated community to Disney. With 6 bedrooms, all with TVs, 4 masters with en suites, and 5.5 bathrooms will sleep up to 12 people in spacious, elegantly furnished style. Close to shops and many restaurants  …see more

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £128 /night

£895 - £1295 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
The perfect location for your dream holiday. our beautiful lakeside villa is set in the exclusive gated community of Sunset lakes, so close to the theme parks, shopping and golf courses yet set in a peaceful private community with a stunning lake view. Our beautiful, spacious 5 bedroom home also has a Games Room and FREE WIFI Internet  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £147 /night

£1029 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Guests also have access and use to the community clubhouse which also has a pool and large area for sunbathing.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £87 /night

£604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Fabulously situated whether you are going to the Theme Parks, Shopping or Dining with a choice of local or major attractions  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £96 /night

£671 - £738 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Cumbrian Lakes is a gated community and is sought after because of its tranquil setting and proximity to Disney. It has four lovely lakes,a children's area, various jogging trails and open spaces. It offers quick and easy access to Walt Disney World and all major attra  …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

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

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 | 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 modern 2 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. This unit can accommodate up to 4 people comfortably with 1 queen and 2 twin sized beds. Also, this property offers a full kitchen i  …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

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

7 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
This beautifully decorated 3bdrm/2bth condo sleeps up to 8 persons located in a resort style gated communtiy just 3 min. away from disney is perfect for a small family looking to have a great time in the surroundings of many wonderful ammenities such as access to commun  …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

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

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

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

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

11 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
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 and five bath  …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 brand new gated community of Oakwater. The condo consists of one king bed, one queen bed, two twin beds, game cube, Internet access, patio, and a fully equipped kitchen. This unit can comfortably accommodate up to  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £140 /night

£975 - £1125 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
***New 58" 3D Blu-Ray Internet TV with Latest Movies*** Magnificent lake and conservation views, Not overlooked, maximum privacy. Southerly facing pool and spa. Huge 62" HDTV, free wifi, free Sat Nav, free BBQ, free Safe and phone calls. Games room with slate bed pool table, HDTV, Wii, Wii Fit, air hockey, fooseball, darts and 7 bikes.  …see more

6 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 brand new gated community of Oakwater, located 1.5 miles from Disney. It sleeps 6 comfortably with 1 king, 1 queen, and 2 twin sized beds. It also comes with a full kitchen inclusive of coffee maker, microwave, ic  …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

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
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 vaca  …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
Floor Plan (The Seville) 2,336 sq. ft. 2 story home with pool and spa (South-West 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  …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

7 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 immaculate 2story condo has screened-balcony with beautiful view of both the lake and climate-controlled pool with Jacuzzi, next to clubhouse, containing gymnasium. Condo has its own garage for storage and protects your car (with shade) from the elements. Kitchen i  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £50 /night

£345 - £495 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa with own pool just 5 minutes from Disney located at Indian Ridge just off SR 545, off SR 192. Easy access to all theme parks, shops and restaurants. Indian Ridge has a community pool, sports pitches, tennis courts and children's play area.  …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

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

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

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

6 Photos

Condo | 2 Bedrooms | sleeps 4

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
This lavishly furnished 2bdrm/2bth condo is located in the gated resort style community of Windsor Palms. This condo will sleep 4 comfortably in 1 queen and 2 twin sized beds. This property also comes with a full kitchen complete with coffee maker, microwave, ice maker,  …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

13 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
Gorgeous 4 Bedroom/3bath home in gated Emerald Island Resort, just 5 minutes from Disney Property and 2 minutes from shopping and restaurants. The home has a private screened in pool and spa plus private game room. Emerald Island Resort is located on 300 a  …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
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

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

6 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 two bedroom/ two bath condo, with queen sleeper sofa, can accommodate up to six people. This unit has a 1 car garage, and is professionally decorated. To make your stay feel more like home, this unit is equipped with all the latest technologies including: XBOX 360,  …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

8 Photos

House | 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 immaculate 3 bedroom 2 bathroom vacation home has a lake view with a private garage. It will comfortably sleep 6 with 2 king and 2 twin sized beds. It includes a full kitchen with coffee maker, microwave, ice maker, and dishwasher, and also offers access to a pool  …see more

7 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
This beautifully decorated 3-bedroom, 2-bath condo is an ideal vacation spot in Orlando for the family or large groups with all the comforts and conveniences of home and then some! One king, one queen, two twins, and a sofa bed provide plenty of room for everyone to rel  …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
Brighton floor plan - 1816 sq.ft. 4 bedroom 3 bath (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. Th  …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

18 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
Welcome to this beautiful home in Kissimmee, Florida, featuring tropical furnishings and facing south for Florida sun year round. With five bedrooms and five baths, this place can easily accommodate up to ten people and is perfect for large groups of friends or family.  …see more

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

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

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

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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

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.