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Kissimmee

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827 Holiday homes

Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

42

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living S  …see more

from £324 / night

£2066 - £2927 / week

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from £324 / night

(54) Excellent 

23

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond our expectations” This was our first villa rental in USA. It exceeded our expectations, a spacious modern villa well appointed, washer , tumble dryer, TV in all rooms, dishwasher, games room with full size pool table, air hockey etc, and a love  …see more

from £90 / night

£575 - £690 / week

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from £90 / night

24

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Massive pool deck for relaxing, south facing with sun all day. Great look out over a conservation area and not over looked.Super comfort furniture. Formal and informal dining areas plus breakfast bar.2 x King sized en suite bedrooms. 1 x Queen and 2 x twin rooms.<br  …see more

from £166 / night

£1160 / week

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from £166 / night

Featured properties

8

Townhouse rental in Kissimmee with golf nearby

Kissimmee / Emerald Isle Kissimmee

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

from £78 / night

£492 / week

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from £78 / night

(13) Excellent 

18

Holiday villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A fantastic place to stay, would highly recommend!” This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to ma  …see more

from £155 / night

£1085 - £1680 / week

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from £155 / night

(2) Excellent 

27

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Great rental experience” As the title of the listing states, this villa was only 5 minutes to Disney. We found the description and the pictures to be quite accurate too. The community is well maintained and it is gated which made us feel secure. Also  …see more

from £185 / night

£1886 / week

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from £185 / night

(5) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from Home. Great Location. Perfect.” The Villa was everything we dreamed of for our first family holiday in Florida. First impressions were just as we expected, Directions to villa were spot on. Swimming pool was fab with inflatables included. Ho  …see more

from £95 / night

£665 / week

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from £95 / night

(2) Very Good 

18

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Nice Villa, Good Amenities, Very helpful owner.” We booked the above villa on the basis of previous reviews and the fact the owner, Mark, called us and spoke to us in person, answering any questions or emails with speed and efficiency. Mark is very h  …see more

from £79 / night

£550 - £750 / week

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from £79 / night

11

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £136 / night

£952 / week

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from £136 / night

(6) Excellent 

16

Holiday villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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

from £82 / night

£558 - £1062 / week

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from £82 / night

37

Central Florida / Kissimmee

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £163 / night

£1137 / week

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from £163 / night

(31) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Really comfortable and relaxing stay, a quality holiday home.” We stayed here over Christmas and New Year. There were 8 family members - ample room for all and we still had a spare bedroom. The pool area was lovely and the villa location was great.  …see more

from £100 / night

£695 - £895 / week

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from £100 / night

(24) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“You must stay in this Home” We have stayed at Emerald Island Resort on several occasions because we like the closeness of the location to the main attractions and the safety of the gated community with 24 hour security. So, when looking for a property  …see more

from £164 / night

£1148 / week

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from £164 / night

(21) Excellent 

21

Villa rental in Sunset Lakes

Kissimmee / Sunset Lakes

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 104 km
  • Swimming pool
“Excellent house and location” Fantastic house with excellent views over the lake Great location with a massive choice of eating out options close by  …see more

from £100 / night

£700 - £840 / week

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from £100 / night

30

Villa accommodation in Kissimmee

Central Florida / Kissimmee

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Air conditioning
  • Private garden
Mickey's Family Funhouse has 7 bedrooms, 5 bathrooms, this villa is the perfect place to sip your morning coffee or enjoy breakfast. Lay back in the private screened in pool area on one of many cushioned loungers.Great Location:Disney Funhouse 's vaca  …see more

from £226 / night

£1558 / week

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from £226 / night

(58) Excellent 

20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Formosa Gardens

7 22 4 nights min

  • 7 bedrooms
  • Sleeps 22
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“This place is heaven!!” Close to all the attractions yet private enough to give you relaxation!!! Can't wait to book here again!! The owners were very easy to work with and very patient with us!!! Thanks again for renting to us!!!  …see more

from £325 / night

£2275 / week

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from £325 / night

10

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Located just off the US192, this four bedroom villa offers your family the perfect home from home during your stay in Orlando. With a large pool deck and a nicely decorated games room as well as a secret short cut to the Disney theme parks making them just a fifteen min  …see more

from £107 / night

£746 / week

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from £107 / night

25

Holiday home in Kissimmee

Central Florida / Kissimmee

4 9 5 nights min

  • 4 bedrooms
  • Sleeps 9
  • 5 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
In life, you always have to make a choice: Do you want plenty of space or a great location? Do you prefer beautiful views or awesome amenities? Can you forgo the luxuries for affordability? Because you can’t have it all. You’ve heard it time and time again.  …see more

from £110 / night

£750 - £1150 / week

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from £110 / night

(12) Excellent 

49

Kissimmee holiday villa rental

Kissimmee / The Hamlets

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Live the American dream in your very own Florida holiday home located in the quiet gated community of The Hamlets. Just off highway 192 in Kissimmee, yet only minutes drive to hundreds of shops & restaurants (some are even within walking distance) and close to Dis  …see more

from £93 / night

£650 - £750 / week

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from £93 / night

19

Holiday home with swimming pool in Kissimmee

Kissimmee / Paradise Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 152 km
  • Swimming pool
  • Child friendly
This is a beautiful four bedroomed town house, equipped to a very high standard. It has it's own splash pool, heating available if necessary, with a safety screen and terrace. The kitchen is equipped with everything you need including, fridge/freezer, microwave, di  …see more

from £148 / night

£1013 - £1175 / week

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from £148 / night

18

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
One of our guests summed this up in their review: “We’ve been visiting homes in this area for the last six years and yours has been my favourite so far! There is nothing you have overlooked. From the games room to the beautiful pool (love the waterfall &ndas  …see more

from £241 / night

£1681 - £2632 / week

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from £241 / night

(8) Excellent 

39

Central Florida / Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 111 km
  • Swimming pool
  • Child friendly

 …see more

from £234 / night

£1639 - £2582 / week

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from £234 / night

(12) Very Good 

59

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £57 / night

£396 / week

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from £57 / night

(15) Excellent 

47

Central Florida / Kissimmee

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 km
  • Swimming pool

 …see more

from £56 / night

£391 / week

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from £56 / night

(1) Excellent 

42

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

 …see more

from £59 / night

£408 - £512 / week

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from £59 / night

(20) Excellent 

123

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£609 / week

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from £87 / night

32

Kissimmee / Paradise Palms

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £99 / night

£1240 - £1372 / week

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from £99 / night

(4) Average 

37

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £54 / night

£373 - £546 / week

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from £54 / night

28

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £106 / night

£635 - £1058 / week

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from £106 / night

(2) Very Good 

68

Central Florida / Kissimmee

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £128 / night

£890 / week

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from £128 / night

90

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £103 / night

£689 / week

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from £103 / night

(8) Excellent 

21

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £41 / night

£287 / week

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from £41 / night

(3) Very Good 

19

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

 …see more

from £70 / night

£511 / week

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from £70 / night

22

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £90 / night

£630 - £835 / week

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from £90 / night

(2) Very Good 

38

Central Florida / Kissimmee

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £82 / night

£532 / week

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from £82 / night

(5) Excellent 

24

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 km
  • Swimming pool

 …see more

from £56 / night

£391 / week

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from £56 / night

(11) Very Good 

48

Central Florida / Kissimmee

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £123 / night

£752 - £976 / week

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from £123 / night

(8) Excellent 

58

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £91 / night

£628 - £693 / week

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from £91 / night

(1) Very Good 

33

Kissimmee / Paradise Palms

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £111 / night

£775 / week

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from £111 / night

(1) Excellent 

32

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £99 / night

£574 - £1148 / week

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from £99 / night