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83 Holiday homes in Kissimmee

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83 Results  |  
9 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £90 /night

£629 - £854 / week

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Key info:

  • Suitable for children of all ages
  • 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

22 Photos

House | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £250 /night

£1746 - £2600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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 | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £182 /night

£1272 - £1629 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
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. This property features all the comforts of home, and more! Windsor Palms is a gor  …see more

Featured properties

15 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £193 /night

£1348 - £2006 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

18 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £222 /night

£1550 - £2325 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

8 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £90 /night

£629 - £854 / week

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Key info:

  • Suitable for children of all ages
  • 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

14 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

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from £193 /night

£1348 - £2006 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

12 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £159 /night

£1112 - £1416 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £90 /night

£629 - £854 / week

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Key info:

  • Suitable for children of all ages
  • 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

12 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £181 /night

£1264 - £1781 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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 four bedrooms and four baths, this prope  …see more

6 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £77 /night

£533 - £802 / week

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Key info:

  • Suitable for children of all ages
  • 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

14 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £222 /night

£1550 - £2325 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

11 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £136 /night

£948 - £1550 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Floor Plan (The Royale Palm) 2,128 sq. ft.2 story townhome. We invite you to enjoy our townhome 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  …see more

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £169 /night

£1182 - £1644 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
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. This property features all the comforts of home, and more in this 5 bedroom, 3.5  …see more

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £193 /night

£1348 - £2006 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This five bedroom vacation home comes complete with five bathrooms, full kitchen, and pool. This spacious property will easily accommodate 10 on two king, one queen, and four twin sized beds. Amenities include a pool, patio, washer/dryer combo, dishwasher, and hot tub.  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £94 /night

£655 - £1050 / week

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Key info:

  • Suitable for children of all ages
  • 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

14 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £94 /night

£655 - £1050 / week

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Key info:

  • Suitable for children of all ages
  • 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

9 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £107 /night

£746 - £1039 / week

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Key info:

  • Suitable for children of all ages
  • 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

7 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £80 /night

£559 - £764 / week

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Key info:

  • Suitable for children of all ages
  • 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

19 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £218 /night

£1521 - £2278 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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 six bedrooms, a sofa bed, a  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £90 /night

£629 - £854 / week

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Key info:

  • Suitable for children of all ages
  • 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

7 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £87 /night

£603 - £913 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
This beautiful spacious 3bdrm/2/bth condo w/ balcony located in the resort style gated community of Windsor Palms is nicely decorated to suit your needs while vacationing. This condo offers wireless internet. It is located just 3 miles from Disney's gates. T  …see more

10 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £136 /night

£948 - £1550 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Floor Plan (The Royale Palm) 2,128 sq. ft. 2 story townhome. We invite you to enjoy our townhome 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  …see more

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £87 /night

£603 - £913 / week

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Key info:

  • Suitable for children of all ages
  • 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

6 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £90 /night

£629 - £854 / week

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Key info:

  • Suitable for children of all ages
  • 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

13 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £159 /night

£1112 - £1416 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

13 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £77 /night

£533 - £802 / week

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Key info:

  • Suitable for children of all ages
  • 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

13 Photos

House | 6 Bedrooms | sleeps 8

5 Nights min stay

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from £191 /night

£1337 - £1802 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

7 Photos

House | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £80 /night

£559 - £764 / week

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Key info:

  • Suitable for children of all ages
  • 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

10 Photos

Villa | 4 Bedrooms | sleeps 10

Short stays welcome

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from £64 /night

£446 / 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
  • Private garden
An exceptional 4 bed 2 bathroom villa furnished to a very high standard with a fantastic management company. Sleeps 10 people (8 in bedrooms 2 on sofa bed). It has a beautiful south facing private pool deck with open views. Games room with full size pool table.  …see more

24 Photos

Townhouse | 2 Bedrooms | sleeps 8

1 night min stay

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from £70 /night

£484 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Enjoy an amazing, family friendly Central Florida vacation right in the heart of Orlando's world famous theme parks and attractions! At Westgate Town Center, you'll discover a world where luxury accommodations and a variety of special resort amenities combine to create an unforgettable vacation experience  …see more

24 Photos

House | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £139 /night

£967 - £1657 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £139 /night

£967 - £1657 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Goofy's Getaway is a stunning five bedroom vacation home located at Windsor Hills Resort in sunny Central Florida  …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.