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412 Holiday homes in Kissimmee

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  • Acadia (15)
  • Bass Lakes Estate (3)
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  • Cumbrian Lakes (22)
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  • Eagle Pointe (5)
  • Emerald Isle Kissimmee (36)
  • Encantada Resort (5)
  • Fiesta Key (4)
  • Formosa Gardens (11)
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  • Oak Island Cove (5)
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  • Windsor Hills Resort (20)
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Filters applied: Heated pool (412)

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412 Results  |  
16 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4.5/5 

5 Nights min stay

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from £65 /night

£450 - £550 / 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
Come watch the sun set at sunset! ideal for families - large solar west facing pool overlooking lake - games room - 52" tv in lounge, tvs in all bedrooms, wireless high speed internet, ps2, unlimited local, long distance and international phone calls free of charge.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £72 /night

£500 - £945 / 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
Fabulous 4 bed / 3 bath villa with pool (Heated at extra cost) on Terra Verde resort only 10 mins from Disney and local golf courses.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 13

3 Nights min stay

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from £128 /night

£895 - £1195 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This quality ,luxury 6 bed, 4.5 bath villa sleeps 12(plus infant) over 3,000sq.ft.of luxury and has its own 30 ft pool with spa. Features such as;Premium TV Package, Games room, Nintendo wii,, Playstation 2,wifi etc Family Friendly, 6 Bed, 4.5 bath Villa with Oversize South facing Pool and Spa, 3miles to WDW  …see more

Featured properties

17 Photos

House | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £81 /night

£565 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
When you're not cooking in your full kitchen or hanging out at home, you'll find that the area is full of dining, shopping, and entertainment. Whatever you're craving for dinner, you're bound to find it within a few minutes of the home!  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 12

Very Good 4.5/5 

1 night min stay

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from £79 /night

£550 - £800 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This 5 Bedroom villa is situated right on Mickeys doorstep on popular Indian Creek community, approximately 2.5 miles from Disney. Large private pool with decking overlooking conservation area, games room. Large selection of restaurants, supermarkets, gift shops nearby. 2.5 miles to Disney, Games room, Large pool and decking overlooking coservation area, near to all ameanities  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £68 /night

£475 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Within the small gated community of Sunset Lakes, we have a newly decorated 4 bed and 3 bath air conditioned villa with a private pool situated on the lake front. The villa also provides cable television, free WiFi and Nintendo Wii The property has a king size master suite,queen sized room, two further twin rooms.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 12

1 night min stay

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from £95 /night

£663 - £901 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 5 bedroom 4 bathroom villa with private pool, spa/jacuzzi and games room with pool table, table football and air hockey. Free wireless internet and free calls to USA and Canada (5p per min to UK). Xbox 360 and DVD player available. Just 5 mins to Disney World.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £158 /night

£1100 - £1250 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in lake Berkley, kissimmee, Florida/. 7 bedroom all with en-suite facilities villa at lake Berkley resort with stunning views across the lake and of the island, peaceful location but only 15 minutes to Disney. Luxury pool seating on extended deck overlooking large pool and spa.  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £113 /night

£790 - £819 / 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
Our stunning 5 bedroomed villa has everything that you could need for a wonderful holiday in the Orlando area. Including fully stocked games room, swimming pool and hyrotherapy spa, gas barbeque and a PC will full internet and wifi access. Our stunning Lakeside Villa will make all your Florida dreams come true. We have tried to think of everything that you should possibly need for the perfect vacation and just some of our features are, PC is high-speed Internet access, infrared gas barbecue on our sun terrace area which has extended decking the hydrotherapists bar and applewood has coloured lighting display that looks wonderful litter for Nightswimming.  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

5 Nights min stay

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from £165 /night

£1155 - £1260 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Situated on the luxury Bellavida resort, this beautiful property has been designed and built to be a spectacular home. With 6 bedrooms and 5 1/2 bathrooms this is the perfect choice for all families and holiday makers in Orlando Florida! All bedrooms are en-suite, with built in wardrobes, television and ceiling fans.  …see more

20 Photos

Townhouse | 3 Bedrooms | sleeps 8

1 night min stay

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from £62 /night

£434 - £589 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury 3 bedroom, 3 bathroom home, with splash pool. Located on a holiday resort complex with fabulous facilities, including huge swimming pool with fun slide. Only 2 miles from Disney.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

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from £529 /night

£3700 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Getaway is a unique luxury villa located within 10 minutes of Disneyworld and features 3 lounges, 7 bedrooms, 12 person home theatre, gym, huge private pool & outdoor kitchen with living space. At over 6500sq ft our home caters for even the largest of groups. Completely refurbished in 2010 The Getaway offers 'brand new everything' with luxury furnishings throughout  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £56 /night

£390 - £450 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This 4 bed, 2 bath, air conditioned home with its own private oversized 31ft enclosed swimming pool is located on the popular Hamilton's Reserve community just 7.1 miles from Disney's Magic Kingdom. This home has everything you will need for a great vacation 7.1 miles from Disney's Magic Kingdom, 4 Beds, 2 Bath, 2 Lounges, PRIVATE Enclosed 31ft Heatable Pool  …see more

13 Photos

Villa | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £144 /night

£1007 - £1696 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
7 Bedrooms, 4 Bathrooms, Large South facing Pool / Spa Near Disney Theme Parks, Games Room, Wi Fi, 60" Internet TV, DVD, Conservation area, Lake views, Fully equiped kitchen, towels provided, suitable for disabled people, local management company, fishing, gold nearby Lovely views of the lake and It is only a short drive from the main theme parks and many golf courses.  …see more

20 Photos

House | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £226 /night

£1579 - £2223 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Spacious 3400 ft, 6 bedoomed home, non smoking, sleeps 12, free wifi,games room,south facing swimming pool,secluded large corner plot. Free wifi, 6 bedrooms,south facing pool, secluded large corner plot , very comfortable home, games room.  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

5 Nights min stay

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from £75 /night

£525 - £843 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Your dream holiday starts here !! Villa Pip is nestled within a 200 acre conservation area and has a South West facing pool and spa that backs onto a beautiful conservation area.. We also offer - Free international calls - Free use of PC / high speed internet  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £93 /night

£650 - £850 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
This beautiful 6 bedroom villa has the privilege of being in the closest residential community to the Disney Theme Parks (2 miles away)5 minutes. It is situated just off of Highway 192 in the stunning location of Rolling Hills. The Villa is just 2 minutes from a large variety of supermarkets, services, restaurants and a walk-in medical centre. There are 6 golf courses within 10 minutes of the Villa and the Villa is ideally placed for outlet malls and factory stores.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

3 Nights min stay

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from £106 /night

£742 - £1039 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Five large bedrooms which can sleep 12 persons comfortably. Some with an en-suite bathroom. Lovely peaceful, quiet 'home from home'. Short drive to Disney World attractions and Shopping Mall and Supermarket. BBQ on request.  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £54 /night

£377 - £504 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
5 Star luxury at affordable rates, this home from home in Sunny Florida is situated in peaceful surrounding on the edge of Kissimme in a rual setting. Just 10 minutes at normal driving speeds from the world famous Disney Parks. The 5 star luxury is reflected in the quality of the fixtures and fittings, with a host of free items.  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £103 /night

£717 - £1003 / week

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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 | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £147 /night

£1024 - £1433 / week

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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

24 Photos

House | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £74 /night

£512 - £758 / week

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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

Condo | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £68 /night

£471 - £758 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
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

19 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £94 /night

£655 / week

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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

18 Photos

House | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £63 /night

£439 - £778 / week

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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

12 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £89 /night

£623 - £826 / week

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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

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from £101 /night

£707 - £938 / week

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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

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from £95 /night

£665 - £889 / week

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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

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from £83 /night

£581 - £784 / week

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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

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from £83 /night

£581 - £784 / week

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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

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from £89 /night

£623 - £875 / week

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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

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £83 /night

£581 - £784 / week

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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

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from £113 /night

£791 - £1092 / week

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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

18 Photos

House | 6 Bedrooms | sleeps 14

2 Nights min stay

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from £137 /night

£959 - £1302 / week

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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

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from £101 /night

£707 - £994 / week

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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

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from £101 /night

£707 - £938 / week

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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

12 Photos

House | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £83 /night

£581 - £784 / week

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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

15 Photos

House | 4 Bedrooms | sleeps 10

1 night min stay

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from £101 /night

£707 - £931 / week

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Key info:

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

8 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £95 /night

£665 - £882 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Internet Access Heated Pool Private Pool Shared outdoor pool (unheated)  …see more

14 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £101 /night

£707 - £931 / week

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Key info:

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

11 Photos

House | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £89 /night

£623 - £826 / week

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Key info:

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

24 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £55 /night

£379 - £435 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located in Grand Palms Resort, this Kissimmee Florida vacation rental is just FIVE miles from the Walt Disney World  …see more

24 Photos

Condo | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £47 /night

£325 - £599 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
With everything you could want such as a fully equipped kitchen and a community outdoor pool, this child friendly Kissimmee, Florida vacation rental condo is the best place to enjoy vacations near Disney World  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

Short stays welcome

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from £152 /night

£1063 - £1395 / week

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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

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £77 /night

£539 - £729 / 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
Spacieuse villa 8 personnes , piscine chauffée , avec vue imprenable sur le lac Spacious villa 8 people, heated pool, with stunning views of the lake  …see more

10 Photos

Townhouse | 3 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £47 /night

£327 - £416 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Beautiful three bedrooms two baths townhouse with amenities. Venetian Bay Villages has a beautiful village concept setting with a resort-style clubhouse that includes gym, 4 pools, business center. There are tennis courts, volleyball, basketball, picnic area, children's  …see more

10 Photos

House | 5 Bedrooms | sleeps 10

1 night min stay

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from £109 /night

£760 - £847 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Casa no condomínio Cubrian Lakes para até 10 pessoas, bela vista para o lago. Agradável experiência em família de passar alguns dias próximo ao mágico mundo da Disney. 5 quartos, um suíte , 3 banheiros, cozinha completa, piscina aquecida e internet wi-fi. Seja bem vindo  …see more

21 Photos

House | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £121 /night

£847 - £977 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
casa orlando casa para alugar em orlando casa perto da disney casa na disney ferias em orlando alugar casa em orlando alugar casa na disney alugar casa perto da disney casa nos estados unidos casa na florida casa em kissimme alugar casa na florida alugar casa feiras eua  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £102 /night

£713 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
VILLA 5 CHAMBRES 3 SALLES DE BAIN GAME ROOM PISCINE SPA BONUS ROOM ORDINATEUR FOURNI PS2 ET JEUX FOURNIS WIFI TELE DANS TOUTES LES CHAMBRES IDEALE POUR LES FAMILLES NOMBREUSES OU GROUPE SITUEE A 10 MIN DES PARCS DISNEY  …see more

15 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £75 /night

£521 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
ACCUEIL FRANCOPHONE SUR PLACE  …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.