List your home
Apply filters
£ to

413 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
  • Acadia (14)
  • Bass Lakes Estate (3)
  • Bellavida Resort (11)
  • Calabria, Orlando (1)
  • Cane Island (2)
  • Chatham Park (3)
  • Compass Bay (2)
  • Coral Cay (2)
  • Creekside (1)
  • Crescent Lakes (10)
  • Crestwynd Bay (7)
  • Crystal Cove Resort (2)
  • Cumbrian Lakes (22)
  • Doral Woods (6)
  • Eagle Pointe (5)
  • Emerald Isle Kissimmee (36)
  • Encantada Resort (5)
  • Fiesta Key (4)
  • Formosa Gardens (11)
  • Hamiltons Reserve (5)
  • Heritage Key (1)
  • Indian Creek (12)
  • Indian Point (17)
  • Indian Ridge (4)
  • Indian Ridge Oaks (5)
  • Kissimmee City (10)
  • Lake Berkley (18)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (4)
  • Lindfields (13)
  • Oak Island Cove (5)
  • Oak Island Harbor (3)
  • Orange Lake Resort (3)
  • Paradise Palms (9)
  • Regal Oaks (2)
  • Remington (3)
  • Reunion Resort (14)
  • Rolling Hills at Formosa (4)
  • Seasons Resort (10)
  • St Cloud (1)
  • Sunset Lakes (7)
  • Tema (1)
  • Terra Verde Resort (8)
  • The Hamlets (1)
  • Trafalgar Village (2)
  • Tuscany, Florida (4)
  • Venetian Bay Villages (10)
  • Veranda Palms (5)
  • Villasol (2)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (21)
  • Windsor Palms (15)
  • Winward Cay (1)

more +

less -

Also consider

Kissimmee
622 properties
New York City
602 properties
Davenport
446 properties
Miami Beach
295 properties
Orlando
106 properties
Inverness, Florida
72 properties
Haines City
71 properties
Clermont, Orlando
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
16 properties
Englewood
13 properties
Clearwater
12 properties
Harrison
12 properties

Filters applied: Heated pool (413)

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
413 Results  |  
15 Photos

Villa | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
-- Next to Walt Disney World. -- Walt Disney Tickets Sold on Site from Resort. -- -- Available At a Huge Discount than market rates. -- -- Available At a Huge Discount than market rates.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Our first floor unit is ideally located within walking distance to the resort clubhouse and its amenities. Close to everything, this community is one of the most sought after communities in Central Florida. Less than 5 miles to Disney!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

Excellent 5/5 

Min stay varies

Add to shortlist

from £179 /night

£1250 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedrooms, gated community, Windsor palms, swimming pool, Jacuzzi, Disney, air conditioned, clubhouse  …see more

Featured properties

14 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

Add to shortlist

from £67 /night

£467 - £615 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Oak Island Cove is located in the middle of all the fun parks and attractions Orlando has to offer, only a few minutes from what makes Orlando so famous. Disney World is only 3 miles away and Universal Studies & Sea World a mere 20 minute  …see more

8 Photos

Townhouse | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

from £46 /night

£318 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Emerald Island has a great location, only minutes from Disney and theres loads of shops and restaurants close by. Our house has a brilliant position right infront of the heated pool and spa and you can just sit on the balcony and chill out after a busy day at the parks  …see more

18 Photos

House | 5 Bedrooms | sleeps 10

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Two lounge and dining areas means this lovely house is suitable for families with children, family reunions, or larger groups travelling together. Large pool and patio area with seating, and great for get together or just relaxing after a hard day at the parks.  …see more

14 Photos

Townhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Enjoy the fabulous climate and amenities of the Central Florida area without breaking the bank. This is a 3 bedroom townhouse, fully air conditioned, with private pool, conveniently located in the recently completed BellaVida resort in Kissimmee.  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Soon You'll Be Staying at a Individually Designed Luxury 4 Bed villa with all of the home comforts you expect.Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some family time.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

from £142 /night

£990 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
South Beach 5 room Art Deco Pool Villa  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
FACILITIES AVAILABLE IN OUR SUPERIOR ACCOMMODATION Indoor open courtyard private swimming pool. Jacuzzi both heated. Large sundeck with sun loungers. 3 large bedrooms all on suit with TV and video. 3 Bathrooms one being disabled equipped. Air conditioning throughout. H When you stay at our luxury villa you will be within three miles of the Disney complex.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

Excellent 5/5 

Min stay varies

Add to shortlist

from £572 /night

£4000 - £4750 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Oasis features 7 bedroom suites all with Private Bathrooms, a huge family room with seating for 14, a dedicated games room with seating area, a separate study with third seating area, a resort style swimming pool, separate kids pool and much more. Your own movie theatre, a summer kitchen & outdoor lounge are just some of the additional luxuries on offer.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury villa on Indian Creek Estate with large south facing Pool & Spa enclosed and not overlooked from the back, only 5 minutes from Disney, Master en-suite room, Queen en-suite room a double room and one Nemo themed kids room, also games room with pool and air hockey.  …see more

19 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £96 /night

£671 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This large 1,755 sq ft ground floor luxury corner unit is located close to the center of Reunion offering convenience and luxury in a peaceful landscaped setting.  …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.