List your home
Apply filters
£ to

85 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 (31)
  • Eagle Pointe (1)
  • Emerald Isle Kissimmee (3)
  • Indian Creek (3)
  • Oak Island Cove (1)
  • Paradise Palms (4)
  • Terra Verde Resort (1)
  • Windsor Hills Resort (16)
  • Windsor Palms (24)

more +

less -

Also consider

Kissimmee
619 properties
New York City
600 properties
Davenport
445 properties
Miami Beach
290 properties
Orlando
104 properties
Inverness, Florida
72 properties
Clermont, Orlando
70 properties
Haines City
70 properties
Cape Coral
51 properties
Rotonda West
48 properties
Manhattan, NY
47 properties
Naples, FL
38 properties
Champions Gate
37 properties
Sarasota
36 properties
Fort Myers
26 properties
Miami
19 properties
Cape Cod
15 properties
Aventura
13 properties
Englewood
13 properties
Clearwater
12 properties

Filters applied: Smokers (85)

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
85 Results  |  
15 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £202 /night

£1408 - £1902 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 12

5 Nights min stay

Add to shortlist

from £202 /night

£1408 - £1902 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

14 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £166 /night

£1159 - £1477 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Brighton floor plan 1816 sqft. 4 bedroom 2 bath A newly renovated 4 bedroom house with game room just minutes away from Disney and golf courses. 1800 sq ft fully equipped with washer and dryer, dishwasher, all bath towels and bed linens provided. This home can ac  …see more

Featured properties

7 Photos

House | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £84 /night

£584 - £797 / week

View

Key info:

  • Great for children of all ages 5
  • 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

5 Nights min stay

Add to shortlist

from £189 /night

£1318 - £1668 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

14 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £202 /night

£1408 - £1902 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £231 /night

£1617 - £2189 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £953 / week

View

Key info:

  • Great for children of all ages 5
  • 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

9 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £95 /night

£659 - £890 / week

View

Key info:

  • Great for children of all ages 5
  • 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

7 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £953 / week

View

Key info:

  • Great for children of all ages 5
  • 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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £90 /night

£629 - £953 / week

View

Key info:

  • Great for children of all ages 5
  • 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

13 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £80 /night

£554 - £836 / week

View

Key info:

  • Great for children of all ages 5
  • 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

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £166 /night

£1159 - £1477 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

7 Photos

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £98 /night

£683 - £1000 / week

View

Key info:

  • Great for children of all ages 5
  • No pets allowed
Luxuriously appointed 3 bedroom, 2 bath top floor unit in the beautiful Windsor Hills resort that sleeps 6 comfortably. This elegantly decorated Kissimmee vacation condo is located in a gorgeous gated community just 5 minutes from the gates of the Magic Kingdom.  …see more

5 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £84 /night

£584 - £797 / week

View

Key info:

  • Great for children of all ages 5
  • 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

13 Photos

House | 4 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £190 /night

£1327 - £1698 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

18 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £231 /night

£1617 - £2189 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

17 Photos

House | 5 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £231 /night

£1617 - £2189 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

8 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £95 /night

£659 - £890 / week

View

Key info:

  • Great for children of all ages 5
  • 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

19 Photos

House | 6 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £227 /night

£1587 - £2141 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

11 Photos

Condo | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £112 /night

£779 - £1084 / week

View

Key info:

  • Great for children of all ages 5
  • 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

13 Photos

House | 6 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £200 /night

£1396 - £1881 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

6 Photos

Condo | 2 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £80 /night

£554 - £836 / week

View

Key info:

  • Great for children of all ages 5
  • 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 | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £84 /night

£584 - £797 / week

View

Key info:

  • Great for children of all ages 5
  • 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

House | 4 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £166 /night

£1159 - £1477 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

14 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £231 /night

£1617 - £2189 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £95 /night

£659 - £890 / week

View

Key info:

  • Great for children of all ages 5
  • 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 £98 /night

£683 - £1000 / week

View

Key info:

  • Great for children of all ages 5
  • 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

13 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £177 /night

£1234 - £1716 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

10 Photos

Villa | 4 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £64 /night

£446 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • 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

House | 5 Bedrooms | sleeps 10

4 Nights min stay

Add to shortlist

from £142 /night

£990 - £1696 / week

View

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

24 Photos

Townhouse | 2 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £71 /night

£495 / week

View

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

Add to shortlist

from £142 /night

£990 - £1696 / week

View

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

12 Photos

Apartment | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £73 /night

£509 - £636 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
CHILDREN FRIENDLY BUT BUILT IN SUCH A WAY THAT NOISE IS NOT AN ISSUE. A PRINT OUT OF CLIENT'S CREDIT CARD WILL BE NEEDED UPON CHECK-IN IN LIEU OF A SECURITY DEPOSIT. UNITS ARE DEEP-CLEANSED BEFORE EVERY BOOKING AND CLEANING FEE IS NOT INCLUDED IN PRICE AND IS USD 85. PRICE CAN BE DIFFERENT FROM MONTH TO MONTH SO PLEASE INQUIRE. D O N O T PAY UNLESS YOU RECEIVE CONFIRMATION  …see more

16 Photos

House | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Suitable for children over
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Townhouse / Townhome - Terra Verde - 03 BEDROOMS  …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.