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Kissimmee

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2,057 Holiday homes

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

(6) Very Good 

34

Townhouse rental in Paradise Palms with indoor pool, golf nearby

Kissimmee / Paradise Palms

4 8 3 nights min

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

from £72 / night

£480 - £960 / week

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from £72 / night

(4) Excellent 

45

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa and ideal location” The villa was lovely, very clean and spacious with a great view of the lake behind. It was situated in an ideal location - especially for Disney! Would definitely stay again.  …see more

from £96 / night

£680 - £780 / week

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from £96 / night

(9) Very Good 

75

Holiday villa with shared pool in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
“Fantastic Relaxing Retreat from the Orlando Hustle and Bustle” We very much enjoyed our stay in this spacious and secure house. It is situated in a safe and quiet gated community less than half an hour's drive from most of the Orlando theme parks and  …see more

from £96 / night

£672 / week

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from £96 / night

Featured properties

(10) Very Good 

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Fab villa” We just returned from a week at the Palm Heaven Villa. The villa is fab and located in the beautiful Terra Verde resort. It is close to the clubhouse and resort pool. The villa itself is very comfortable and has everything you need. The poo  …see more

from £65 / night

£495 / week

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from £65 / night

(8) Very Good 

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Lovely Villa, well placed” Villa was clean & spacious. Pool was lovely & clean with nice garden view. Mostly quiet neighbourhood. Very close to 192 with all the restaurants & shopping. Ian was easy to contact & kept in touch throughout the stay. Pool  …see more

from £65 / night

£450 / week

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from £65 / night

(4) Excellent 

21

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“great villa with a great pool area” Not far from all the theme parks and a great pool area to chill out after a long day. The villa was in good condition and equipped with all the home comforts you could need for a great holiday  …see more

from £115 / night

£700 - £900 / week

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from £115 / night

(1)  

5

Kissimmee holiday apartment rental

Central Florida / Kissimmee

1 4 7 nights min

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

from £50 / night

£350 - £650 / week

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from £50 / night

(1) Excellent 

84

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £112 / night

£784 - £1138 / week

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from £112 / night

(15) Excellent 

37

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“One word to sum up this villa...... PERFECT !!!” Choosing a villa was quite a hard task to ensure that the whole family enjoyed their vacation in Florida. It needed to be centrally located to all the main parks, be furnished to a good standard & have  …see more

from £113 / night

£752 - £920 / week

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from £113 / night

(30) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Best Florida Villa - by far !!!” We have spent many many weeks at this villa and when it isn't available for our trips to Florida nothing we stay at compares !!! It is a great villa, owned by an owner who cares. Well equipped, south facing, very pri  …see more

from £135 / night

£800 - £995 / week

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from £135 / night

(5) Very Good 

88

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 4 nights min

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

from £95 / night

£840 / week

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from £95 / night

(8) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £54 / night

£344 - £536 / week

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from £54 / night

(1) Average 

23

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 8 3 nights min

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

from £72 / night

£480 / week

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from £72 / night

(5) Very Good 

74

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Lovely villa” Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slightly further away from International D  …see more

from £108 / night

£756 / week

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from £108 / night

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool

from £82 / night

£570 - £730 / week

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from £82 / night

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 Min stay varies

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

from £52 / night

£340 - £668 / week

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from £52 / night

24

Holiday villa in Kissimmee

Kissimmee / Rolling Hills at Formosa

4 8 Min stay varies

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

from £81 / night

£565 - £695 / week

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from £81 / night

(6) Excellent 

18

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent living in secure environment for family” Well equipped house for a family, from kitchen, over bedrooms and living area to pool, close to attractions, dining and shopping  …see more

from £100 / night

£695 - £750 / week

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from £100 / night

(6) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super villa” Great for all age groups - has everything you would ever need - teenagers loved the table tennis plus pool. 8 month old grandaughter had cot, toys high hair. The villa is close to shops & theme parks. Quiet estate with villa overlooking l  …see more

from £100 / night

£700 / week

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from £100 / night

23

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £188 / night

£1200 - £1840 / week

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from £188 / night

(35) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20  …see more

from £99 / night

£675 / week

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from £99 / night

(3) Excellent 

24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 Min stay varies

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

from £90 / night

£580 - £1000 / week

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from £90 / night

16

Townhouse rental in Venetian Bay Villages with shared pool

Kissimmee / Venetian Bay Villages

3 8 Min stay varies

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

from £76 / night

£532 - £728 / week

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from £76 / night

(13) Excellent 

60

Holiday condo rental

Kissimmee / Legacy Dunes Resort

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 78 km
  • Swimming pool
“Excellent value and great location!” Lovely apartment, really comfortable and spotlessly clean. We received 2 parking passes and there was always parking available at the door. Complex is quiet, secure and nicely landscaped, pool area is great. Locati  …see more

from £50 / night

£350 - £450 / week

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from £50 / night

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa and resort in good location for attractions” Stayed in the villa for 2 weeks. There were 10 of us yet the villa was so roomy. Very comfortable and modern with all you could need. The paradise palms resort is also excellent. Great  …see more

from £200 / night

£1400 - £1680 / week

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from £200 / night

(3) Very Good 

43

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

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

from £78 / night

£546 / week

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from £78 / night

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a  …see more

from £171 / night

£1200 / week

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from £171 / night

(11) Excellent 

23

Holiday villa in Hamilton's Reserve

Kissimmee / Hamilton's Reserve

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
“Brilliant villa - perfect place for the perfect holiday” Stayed at the villa as part of a group of 4 adults and 4 children, aged from 4-9. Villa was everything we had hoped it would be and more. Photos did not do it justice. The size of the pla  …see more

from £98 / night

£685 - £1240 / week

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from £98 / night

(1) Excellent 

33

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great base for a family holiday” Having used other villas around Orlando I came across this one as our normal one was booked, I contacted the owner who could not of been more helpfull and booked up our stay. When we arrived at the villa it was a  …see more

from £140 / night

£980 / week

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from £140 / night

(5) Very Good 

29

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £150 / night

£1050 - £1330 / week

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from £150 / night

22

Kissimmee holiday villa rental

Kissimmee / Winward Cay

3 8 7 nights min

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

from £50 / night

£350 - £500 / week

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from £50 / night

46

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £96 / night

£640 - £824 / week

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from £96 / night

19

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly

from £235 / night

£1640 / week

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from £235 / night

(3) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £128 / night

£904 - £1328 / week

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from £128 / night

(1) Excellent 

20

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £240 / night

£880 - £2232 / week

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from £240 / night

(3) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £165 / night

£1154 / week

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from £165 / night

(1)  

14

Remington holiday villa rental

Kissimmee / Remington

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £96 / night

£672 / week

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from £96 / night

(16) Excellent 

28

Holiday villa with golf nearby in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £118 / night

£825 - £1090 / week

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from £118 / night

(1) Excellent 

17

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

from £112 / night

£784 / week

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from £112 / night

(6) Excellent 

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

from £130 / night

£840 - £1090 / week

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from £130 / night

1