List your home
Apply filters
£ to

80 Holiday homes in Kissimmee

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • USA East Coast Clear
  • Florida Clear
  • Orlando Disney Area Clear
  • Kissimmee Clear
  • All suburbs
  • Crestwynd Bay (28)
  • Eagle Pointe (1)
  • Emerald Isle Kissimmee (3)
  • Indian Creek (3)
  • Oak Island Cove (1)
  • Paradise Palms (4)
  • Windsor Hills Resort (16)
  • Windsor Palms (24)

more +

less -

Property type

more +

less -

Also consider

Kissimmee
613 properties
Davenport
438 properties
New York City
412 properties
Miami Beach
236 properties
Orlando
104 properties
Inverness, Florida
72 properties
Haines City
69 properties
Clermont, Orlando
68 properties
Cape Coral
44 properties
Manhattan, NY
44 properties
Rotonda West
40 properties
Champions Gate
38 properties
Naples, FL
33 properties
Sarasota
21 properties
Fort Myers
16 properties
Miami
16 properties
Cape Cod
15 properties
Clearwater
13 properties
Englewood
13 properties
Anna Maria Island
9 properties

Filters applied: Smokers (80)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
80 Results  |  
12 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £159 /night

£1112 - £1416 / week

View

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

14 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £222 /night

£1550 - £2325 / week

View

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

22 Photos

House | 6 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £250 /night

£1746 - £2600 / week

View

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

Featured properties

15 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £218 /night

£1521 - £2278 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £193 /night

£1348 - £2006 / week

View

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

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £195 /night

£1360 - £1889 / week

View

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 property features all the comforts of home, and more! Private backyard with beautiful Florida Sunsets, a large pool with spa. The hom  …see more

7 Photos

House | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £80 /night

£559 - £764 / week

View

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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £854 / week

View

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

13 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £77 /night

£533 - £802 / week

View

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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £94 /night

£655 - £1050 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
Newly decorated and upgraded 1st floor 3 bedroom, 2 bath condo. This home comes with a 42" flat screen TV in the living room with a Playstation 3 game system, flat screen TV's in each of the bedrooms (two 32" and one 24" with DVD). The kitchen comes  …see more

10 Photos

House | 5 Bedrooms | sleeps 11

5 Nights min stay

Add to shortlist

from £195 /night

£1360 - £1889 / week

View

Key info:

  • Suitable for children of all ages
  • 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

House | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £854 / week

View

Key info:

  • Suitable for children of all ages
  • 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

6 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £854 / week

View

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

8 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £854 / week

View

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

15 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £182 /night

£1272 - £1629 / week

View

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

11 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £136 /night

£948 - £1550 / week

View

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

6 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £94 /night

£655 - £1050 / week

View

Key info:

  • Suitable for children of all ages
  • 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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £854 / week

View

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

7 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £87 /night

£603 - £913 / week

View

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

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £169 /night

£1182 - £1644 / week

View

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

17 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £195 /night

£1360 - £1889 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

13 Photos

House | 4 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £182 /night

£1272 - £1629 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

13 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £159 /night

£1112 - £1416 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Sunrise Sunset Villa is nestled in the exclusive Winsor Palms community, less than 3 miles from Walt Disney World in Kissimmee, Florida. With 4 bedrooms and 2 bathrooms, this fully air-conditioned, elegant, professionally decorated, luxurious Orlando vacation home is pe  …see more

10 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £87 /night

£603 - £913 / week

View

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 condo in the Windsor Palms Resort. Attention to every detail ha  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £222 /night

£1550 - £2325 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

6 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £80 /night

£559 - £764 / week

View

Key info:

  • Suitable for children of all ages
  • 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

15 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £250 /night

£1746 - £2600 / week

View

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 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

5 Nights min stay

Add to shortlist

from £80 /night

£559 - £764 / week

View

Key info:

  • Suitable for children of all ages
  • 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

10 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £136 /night

£948 - £1550 / week

View

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

6 Photos

Condo | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £77 /night

£533 - £802 / week

View

Key info:

  • Suitable for children of all ages
  • 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

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.