List your home
Apply filters
£ to

524 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 (19)
  • Bass Lakes Estate (2)
  • Bellavida Resort (10)
  • Cane Island (5)
  • Chatham Park (3)
  • Compass Bay (2)
  • Coral Cay (3)
  • Creekside (1)
  • Crescent Lakes (6)
  • Crestwynd Bay (37)
  • Crystal Cove Resort (1)
  • Cumbrian Lakes (22)
  • Doral Woods (6)
  • Eagle Pointe (6)
  • Emerald Isle Kissimmee (28)
  • Encantada Resort (5)
  • Fiesta Key (1)
  • Formosa Gardens (9)
  • Hamiltons Reserve (2)
  • Heritage Key (1)
  • Indian Creek (14)
  • Indian Point (20)
  • Indian Ridge (4)
  • Indian Ridge Oaks (6)
  • Kissimmee City (12)
  • Lake Berkley (16)
  • Lake Marion (1)
  • Liberty Village (4)
  • Lindfields (14)
  • Lucaya Village (1)
  • Oak Island Cove (5)
  • Oak Island Harbor (1)
  • Orange Lake Resort (2)
  • Paradise Palms (14)
  • Regal Oaks (3)
  • Remington (6)
  • Reunion Resort (41)
  • Rolling Hills at Formosa (6)
  • Seasons Resort (11)
  • St Cloud (1)
  • Sunset Lakes (5)
  • Tema (1)
  • Terra Verde Resort (7)
  • The Hamlets (2)
  • Trafalgar Village (3)
  • Tuscany, Florida (2)
  • Venetian Bay Villages (11)
  • Veranda Palms (5)
  • Villasol (2)
  • Vista del lago (1)
  • Westside (2)
  • Windsor Hills Resort (41)
  • Windsor Palms (36)
  • Winward Cay (1)

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: Restricted mobility (524)

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
524 Results  |  
24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £103 /night

£717 - £1003 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This 2,324 sq.ft pool home is located within the Patriot's Landing neighborhood of the exclusive Reunion Resort. This very distinctive neighborhood offers Key West-style luxury homes with pastel color schemes, surrounded on three sides by natural conservation areas and  …see more

24 Photos

House | 3 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located in the upscale Reunion Resort community of Centre Court Ridge.  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £147 /night

£1024 - £1433 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This 5 bed 4.5 bath 3,000 sq ft luxury Villa is located in the Liberty Bluff neighborhood of Reunion Resort. This home has superb views and overlooks the 6th Tee and Hole of the Legacy / Arnold Palmer Golf Course.  …see more

Featured properties

24 Photos

Condo | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located in the upscale Reunion Resort community of Centre Court Ridge.  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 6

rentals_reviews_rating_1 

4 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
3 Bed Third Floor Corner Unit Condo With Golf Membership Located in the upscale Reunion Resort community of Center Court Ridge.  …see more

23 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Top Floor Corner Unit Condo With Stunning Golf Views Spacious 3 Bed Luxury Condo with Membership Located in the upscale Reunion Resort community of Center Court Ridge.  …see more

19 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £94 /night

£655 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

24 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £158 /night

£1106 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Contemporary style home, corner lot with games room  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £94 /night

£655 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located in the upscale Reunion Resort community of The Villas North and overlooking the the Independence golf course  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

Add to shortlist

from £498 /night

£3480 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This unique, one of a kind, beautiful, private custom Estate Home features over 8,200 sq/ft of luxury accommodation and balconies. This 'WOW!' factor home is private, quiet and not overlooked.  …see more

23 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £182 /night

£1270 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This professionally decorated 3,284 sq ft. home is located within the Liberty Bluff neighborhood of Reunion. Furnished to appeal to all, whether it's a family vacation, a golfing adventure, or a couple of families out to see Disney and all Orlando has to offer!  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

Add to shortlist

from £126 /night

£881 - £1290 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Prime Location within the Resort - walk to the Grande!  …see more

24 Photos

Condo | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £94 /night

£655 - £881 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This spectacular 5* 2 bed, 2 bath condo is located on the 6th floor of the Reunion Grande Luxury Suite Hotel. This sixth floor unit overlooks the Golf Driving range and faces the Disney night time fireworks.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 13

5 Nights min stay

Add to shortlist

from £191 /night

£1331 - £2150 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Prime Location within the Resort - walk to the Grande!  …see more

13 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £68 /night

£471 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
3 Bed Terraces Condo in Reunion Resort Close to Disney Located in the upscale Reunion Resort community at the Reunion Terraces, this luxuriously appointed ground floor condo boasts a luxury contemporary furniture package.  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £115 /night

£799 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
All brand new furniture July 2013. Furnished to the standard of a 5 Star hotel,this 3 bed condo is located in The Villas South at Cabana Court close to the heart of Reunion Resort with views of the Tom Watson designed golf course.  …see more

21 Photos

Condo | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £68 /night

£471 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Third Floor Condo With Stunning Golf Views - Spacious 3 Bed 3 Bath Luxury Condo Located in the upscale Reunion Resort community The Villas North and overlooking the The Independence golf course by Tom Watson  …see more

22 Photos

Townhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £79 /night

£553 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Luxury Reunion Town Home next to the pool  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £77 /night

£533 - £815 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Spacious 3 Bed 3 Bath Luxury Condo with Golf Views and Resort membership ALL BRAND NEW LUXURY FURNITURE AND APPLIANCES MAY 2013  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £129 /night

£901 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
2,000 sq,ft. Modern Decor in the centre of Reunion Resort  …see more

20 Photos

Condo | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £68 /night

£471 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This large third floor luxury corner unit is located close to the center of Reunion This large 1530 sq ft third floor luxury corner unit is located close to the center of Reunion offering convenience and luxury in a peaceful landscaped setting.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £188 /night

£1310 - £2150 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
6 Miles to Disney  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £305 /night

£2129 - £2293 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
Wet bar, Summer Kitchen, Outdoor /Fireplace This custom home, elegantly decorated to a French Country Style features a private pool and spa, separate guest suite, 4,400 sq ft of spacious living areas, a Cinema room and stunning golf views!  …see more

24 Photos

House | 7 Bedrooms | sleeps 18

1 night min stay

Add to shortlist

from £457 /night

£3193 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
7 Bedroom, 7.5 Bath, 6,500 sq ft, Stunning contemporary home  …see more

21 Photos

Condo | 2 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £88 /night

£615 - £819 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Third floor unit overlooking the golf driving range with night time Disney fireworks views  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £126 /night

£881 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This luxury single story 4 bedroom, 2.5 bath, 2,000 sq.ft villa is in a great location within the Homestead neighborhood of the exclusive Reunion Resort.  …see more

10 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £74 /night

£512 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
1 Bedroom Condo, 100ft from Pool, Hot tubs, Pavilion, Fitness room, Games room  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Beautiful Decor - New Furniture May 2013 Located in the upscale Reunion Resort community of Center Court Ridge.  …see more

23 Photos

Condo | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £74 /night

£512 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Top Floor (4th), Corner Unit Condo With Stunning Golf Views and Resort Membership This fourth floor, corner unit with stunning Golf views has three beds and three bathrooms.  …see more

24 Photos

House | 5 Bedrooms | sleeps 12

1 night min stay

Add to shortlist

from £322 /night

£2252 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
5 Bed, 5.5 Bath, Over 5,000 sq ft exceptional Reunion pool home  …see more

21 Photos

Condo | 3 Bedrooms | sleeps 8

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £68 /night

£471 - £758 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Second Floor Condo With Stunning Golf Views Spacious 3 Bed 3 Bath Luxury Condo with Golf Membership Located in the upscale Reunion Resort community of The Villas North at Sandy Ridge Drive and overlooking the The Independence golf course by Tom Watson  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £63 /night

£439 - £778 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This third floor, corner unit condo with stunning Golf views has three beds and three bathrooms. This condo is in one of the most popular neighborhoods in Reunion Resort. Centre Court Ridge is a centrally-located community, made up of a large 55,000 gallon heated swimmi  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £152 /night

£1063 - £1395 / week

View

Late Deal: save up to £437

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
5 star Luxury villa, you will not be disappointed at this truly charming villa, it is simply out of this world. Stunning decor and its perfectly located for access the theme parks. Sleeps up to 14. - 6 Bedrooms and 5 + 2½ bathrooms luxury villa with a total of 4184 sq ft  …see more

18 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £77 /night

£539 - £882 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Hot Tub/Jacuzzi Television Satellite or cable TV DVD Player  …see more

12 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £89 /night

£623 - £826 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Sunset Lakes is a small gated community located right in the heart of Disneys most desirable area  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £938 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Satellite or cable TV DVD Player Television  …see more

20 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £95 /night

£665 - £889 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Internet Access eated Pool Private Pool DVD Player Satellite or cable TV VCR Garage  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool DVD Player VCR Television Satellite or cable TV  …see more

8 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Television Satellite or cable TV VCR  …see more

13 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £89 /night

£623 - £875 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Heated Pool Shared outdoor pool (unheated) VCR DVD Player Television Satellite or cable TV  …see more

10 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £77 /night

£539 - £889 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access DVD Player Satellite or cable TV Shared outdoor pool (unheated)  …see more

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Private Pool Shared outdoor pool (unheated) Heated Pool VCR Satellite or cable TV Television DVD Player  …see more

18 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

Add to shortlist

from £113 /night

£791 - £1092 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Private Pool Television Satellite or cable TV DVD Player  …see more

16 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £77 /night

£539 - £889 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Shared outdoor pool (unheated) atellite or cable TV Television DVD Player VCR  …see more

18 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

Add to shortlist

from £137 /night

£959 - £1302 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Internet Access Heated Pool Private Pool VCR DVD Player Television  …see more

17 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £994 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Heated Pool Private Pool Shared outdoor pool (unheated) Satellite or cable TV Television DVD Player VCR  …see more

22 Photos

House | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £938 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Intern Private Pool Shared outdoor pool (unheated) VCR Satellite or cableTV DVD Player Television  …see more

7 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Private Pool DVD Player VCR Television Satellite or cable TV  …see more

12 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
Internet Access Private Pool Heated Pool Heated Pool Satellite or cable TV VCR Television DVD Player  …see more

12 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £83 /night

£581 - £784 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Internet Access Heated Pool Private Pool Satellite or cable TV Television DVD Player  …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.