Kissimmee Villas, Holiday rentals and apartments

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Kissimmee

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4,641 Holiday homes

(17) Excellent 

14

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“3 weeks of luxury” I have just arrived back in the UK from a fantastic 3 weeks in this Villa and am already looking at booking it again for next year. Excellent location in terms of parks, shops, places to eat and night time peace. Lovely clean, spa
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from £70 / night

£465 - £595 / week

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from £70 / night

(1) Excellent 

18

Central Florida / Kissimmee

4 10 Min stay varies

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

from £104 / night

£722 / week

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from £104 / night

(11) Excellent 

69

Townhouse rental in Fiesta Key with golf nearby

Kissimmee / Fiesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool

from £59 / night

£411 / week

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from £59 / night

(3) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

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

from £67 / night

£465 / week

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from £67 / 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 £184 / night

£1172 - £1797 / week

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from £184 / night

(14) Excellent 

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

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

from £84 / night

£550 - £700 / week

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from £84 / night

(8) Excellent 

14

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“A HOLIDAY TO REMEMBER” Cumbrian lakes drive is a well appointed 8 bed villa in very pleasant surroundings. We stayed there 4 adults and 2 young children aged 6 & 8 for 2 weeks. It is within easy access of all the parks, the malls etc and only a shor
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from £90 / night

£630 - £795 / week

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from £90 / night

(6) Excellent 

60

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £90 / night

£630 / week

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from £90 / night

(4) Excellent 

39

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children age 5+
“Very enjoyable stay at Simba's Magic home.” Very enjoyable stay at Simba's Magic home. Dealing with the owner, Sri, was super easy and our group really liked the house. Having stayed in Emerald Island several times, this was the best property we've r
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from £184 / night

£1797 / week

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from £184 / night

(2) Very Good 

49

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

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

from £125 / night

£895 - £1565 / week

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from £125 / night

28

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £235 / night

£1407 - £1969 / week

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from £235 / night

(2) Very Good 

18

Central Florida / Kissimmee

3 8 5 nights min

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

from £78 / night

£542 / week

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from £78 / night

(6) Excellent 

15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“Fabulous house with all you would need being away from home !” We enjoyed our stay very much. The pool was amazing , and we used it every day. It was in a good quiet residential area. Close to all amenities, parks and shops. The children were thri
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from £60 / night

£425 - £595 / week

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from £60 / night

(8) Very Good 

49

Home rental in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Our stay in Florida was made that much more enjoyable staying here” 995 Lake Berkley Drive, was a great place for us to stay during our recent two week trip to Florida. The estate itself is very impressive, clean and well maintained. A safe and secure
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from £106 / night

£688 - £833 / week

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from £106 / night

(1) Excellent 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

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

from £86 / night

£600 - £750 / week

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from £86 / night

(1) Very Good 

19

Holiday apartment with shared pool in Kissimmee

Kissimmee / Windsor Palms

3 6 Min stay varies

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

from £62 / night

£433 / week

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from £62 / night

(2) Excellent 

71

Holiday villa with shared pool in Kissimmee City

Kissimmee / Kissimmee City

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect in every way” we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have in your own kitchen at home s
…see more

from £80 / night

£550 / week

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from £80 / 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
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from £65 / night

£450 / week

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from £65 / night

(19) Very Good 

30

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic” 1   person found this review helpful Our stay in the villa was incredibly pleased! Zakir, was quick to respond, and very easy to work with.We have stayed in the Orlando/Kissimee area before, but this was our best stay so far. Vill
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from £71 / night

£547 / week

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from £71 / 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
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from £137 / night

£958 / week

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from £137 / night

(4) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 Min stay varies

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

from £85 / night

£595 - £910 / week

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from £85 / 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

(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 £110 / night

£766 / week

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from £110 / 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

(1) Average 

52

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £80 / night

£495 - £695 / week

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from £80 / night

(7) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

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

from £80 / night

£560 - £665 / week

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from £80 / night

(6) Excellent 

75

Holiday villa rental

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Huge villa in a quiet residential area and close to Disney” This villa is huge and finished to an excellent standard. It is well appointed, very spacious with a great pool and Jacuzzi. Plenty of room to unwind after a hard day at a Park. The villa is
…see more

from £106 / night

£676 - £801 / week

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from £106 / night

(7) Excellent 

30

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
“Excellent property and very helpful owners” This house is excellent and very well maintained. It had all the amenities / facilities we needed and in good working order. Very comfortable and easy to relax after long days at the theme parks. Julie and M
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from £105 / night

£550 - £670 / week

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from £105 / night

(9) Very Good 

22

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £99 / night

£690 - £821 / week

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from £99 / 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 £235 / night

£860 - £2179 / week

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from £235 / night

(2) Very Good 

100

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

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

from £110 / night

£766 - £1111 / week

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from £110 / night

(8) Excellent 

43

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 114 km
  • Swimming pool
  • Child friendly

from £75 / night

£525 / week

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from £75 / 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
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from £100 / night

£695 - £750 / week

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from £100 / night

(2) Very Good 

14

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 10 4 nights min

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

from £106 / night

£731 / week

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from £106 / night

(10) Very Good 

61

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“beautiful” the house is beautiful and quiet, we had a great time and will definitely return, Kevin and Anne and their management are friendly and always available. thanks for everything
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from £115 / night

£795 - £1540 / week

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from £115 / night

64

Holiday villa in Lindfields

Kissimmee / Lindfields

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

from £71 / night

£497 / week

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from £71 / 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

(2) Excellent 

37

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £79 / night

£547 - £782 / week

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from £79 / 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
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from £171 / night

£1200 / week

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from £171 / night

(1) Excellent 

57

Home rental in Kissimmee

Kissimmee / Oak Island Harbor

4 8 4 nights min

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

from £204 / night

£1422 / week

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from £204 / night

1