Villas in Kissimmee and Holiday rentals - Holiday Lettings - Holiday Rentals Kissimmee

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Kissimmee

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5,103 Holiday homes

(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
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from £108 / night

£750 / week

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from £108 / night

(12) Excellent 

Certificate of Excellence

16

Villa rental in Kissimmee

Kissimmee / Indian Creek

4 8 Min stay varies

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

Certificate of Excellence

from £100 / night

£700 - £1100 / week

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from £100 / night

(5) Excellent 

Certificate of Excellence

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
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Certificate of Excellence

from £115 / night

£700 - £895 / week

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from £115 / night

27

Holiday villa in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £181 / night

£1071 - £2126 / week

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Responds fast!
avg. 1 hour 40 minutes

from £181 / night

(4) 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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Responds fast!
avg. 1 hour 27 minutes

from £78 / 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.
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from £96 / night

£675 - £774 / week

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from £96 / night

(2) Very Good 

35

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“FANTASTIC!” I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to have them play frisbee and soccer. The loc
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from £91 / night

£635 / week

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from £91 / night

14

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

5 10 Min stay varies

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

from £134 / night

£934 / week

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from £134 / 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 £138 / night

£965 / week

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from £138 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£1050 - £1150 / week

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from £150 / night

(9) 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
“Top villa, ideal location.” We have just returned from a wonderful 2 weeks stay at this villa, it met our expectations and some, all of the rooms were spacious and well equipped, the beds were all very comfortable and it accommodated our disabled son
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from £108 / night

£699 - £846 / week

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Responds fast!
avg. 1 hour 14 minutes

from £108 / night

(4) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Remington

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Great vacation” We had a great holiday . The villa is lovely and very spacious. All home comforts and more. There were 7 of us and we had plenty of room (could comfortably sleep 10). The location is ideal for parks and shopping malls with just a short
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from £75 / night

£525 - £910 / week

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from £75 / night

(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

£477 - £794 / week

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Responds fast!
avg. 2 hours 41 minutes

from £72 / night

85

Holiday villa with swimming pool 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 £95 / night

£665 - £1000 / week

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Responds fast!
avg. 1 hour 22 minutes

from £95 / night

(1) Excellent 

5

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent experience” It's a resort within a golf course. Very close to Disney World and other attractions. Staff was very friendly and helpful. Pools are wonderful for the kids. The resort was close to supermarket. It was a wonderful destination for
…see more

from £120 / night

£834 / week

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from £120 / night

(1) Excellent 

25

Holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

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

from £125 / night

£875 / week

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Responds fast!
avg. 1 hour 12 minutes

from £125 / night

27

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 1 night min

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

from £54 / night

£378 / week

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from £54 / night

(24) Excellent 

27

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • 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
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from £135 / night

£945 - £1250 / week

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from £135 / night

(2) Very Good 

38

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £178 / night

£1812 / week

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Responds fast!
avg. 52 minutes

from £178 / night

(1) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

5 12 3 nights min

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

from £154 / night

£1075 / week

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from £154 / 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 £108 / night

£743 / week

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from £108 / night

9

Holiday townhouse in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £76 / night

£528 - £723 / week

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from £76 / night

40

Holiday home accommodation

Central Florida / Kissimmee

5 12 2 nights min

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

from £118 / night

£822 / week

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from £118 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

3 6 6 nights min

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

from £88 / night

£596 / week

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from £88 / night

28

Home rental in Kissimmee

Central Florida / Kissimmee

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £132 / night

£924 / week

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Responds fast!
avg. 31 minutes

from £132 / 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
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from £100 / night

£700 - £840 / week

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from £100 / night

37

Kissimmee holiday home rental

Central Florida / Kissimmee

6 14 3 nights min

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

from £158 / night

£1101 / week

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from £158 / night

23

Guest house rental in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

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

from £199 / night

£1389 - £2342 / week

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from £199 / night

(23) Excellent 

Certificate of Excellence

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
“Gorgeous villa !” Our first visit to Florida and we had an amazing time i really can't see us going any where else.. the villa is beautiful I felt like a queen for two weeks :) everything u need and more the location is so peaceful, perfect for relaxi
…see more

Certificate of Excellence

from £107 / night

£750 - £900 / week

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Responds fast!
avg. 1 hour 42 minutes

from £107 / night

56

Holiday apartment with shared pool in Kissimmee

Central Florida / Kissimmee

3 6 2 nights min

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

from £71 / night

£457 / week

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from £71 / night

29

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

from £60 / night

£417 - £627 / week

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from £60 / night

(35) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Regal Oaks

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Family trip” Me and my family stayed at Vic's place. There's no place I would call home like this one. We love it there. Very spacious and clean, Close to fun spot where the kids would just walk there whenever they want.close to plenty of restraunts,s
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from £80 / night

£560 - £650 / week

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from £80 / 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

Holiday villa rental

Central Florida / Kissimmee

3 8 Min stay varies

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

from £66 / night

£460 - £599 / week

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Responds fast!
avg. 1 hour 30 minutes

from £66 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

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

from £85 / night

£595 / week

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Responds fast!
avg. 3 hours 8 minutes

from £85 / night

32

Villa rental in Oak Island Cove

Kissimmee / Oak Island Cove

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £130 / night

£886 - £1004 / week

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Responds fast!
avg. 24 minutes

from £130 / night

(33) 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
“Our Family 4th of July Vacation” I was looking for a place where my family and myself could go to spend time in Florida from where I live in NYC. We chose the perfect location. Check in was simple, directions to the home were easy to understand, and i
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from £107 / night

£745 - £895 / week

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from £107 / 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 £68 / night

£473 / week

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Responds fast!
avg. 3 hours 9 minutes

from £68 / night

(3) Excellent 

11

Holiday hotel apartment in Kissimmee

Kissimmee / Compass Bay

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Air conditioning
“Near Disney, Good Price, Beautiful Place” We would stay again. we stayed here and drove to SeaWorld 3 days. very convenient. liked the fact it was a block off the main road. liked where it was near Fun Town for the kids, go cart track walking distan
…see more

from £103 / night

£731 / week

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Responds fast!
avg. 1 hour 29 minutes

from £103 / night

15

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

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

from £84 / night

£584 / week

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from £84 / night

1