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

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Kissimmee

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5,421 Holiday homes

4

Holiday home letting

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £111 / night

£772 - £1120 / week

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from £111 / 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
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from £178 / night

£1812 / week

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Responds fast!
avg. 52 minutes

from £178 / night

(1) Excellent 

35

Holiday home rental

Central Florida / Kissimmee

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £150 / night

£1050 / week

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Responds fast!
avg. 31 minutes

from £150 / night

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Harbor

4 8 Min stay varies

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

from £119 / night

£985 - £1142 / week

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from £119 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £239 / night

£1112 - £2135 / week

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from £239 / night

13

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 10 Min stay varies

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

from £112 / night

£735 - £913 / week

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from £112 / night

(13) Very Good 

Certificate of Excellence

47

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Outstanding Villa - Real Home from Home” Superb villa - really clean, airy and well-decorated with a lovely pool and patio area. Plenty of room for everyone in the 4 bedrooms & especially liked having 3 bathrooms to make leaving for the parks much qui
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Certificate of Excellence

from £66 / night

£460 - £690 / week

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from £66 / night

(19) Very Good 

13

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Point

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A beautiful, clean, home away from home!” We are staying for the month of February in this absolutely awesome, Prairie Point Blvd.home. It's comfortable, spacious and clean, and the pool is to die for! We would highly recommend this home to anyone!
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from £80 / night

£550 - £680 / week

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from £80 / night

(5) 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 £71 / night

£552 - £788 / week

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Responds fast!
avg. 1 hour 19 minutes

from £71 / night

(17) Very Good 

Certificate of Excellence

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very clean and with everything you need!” The place was big for being an apt, clean, close to everything but quite. The instructions were clear and chris replayed me back an email almost instantly. It was the first time renting a place by internet,
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Certificate of Excellence

from £68 / night

£465 / week

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Responds fast!
avg. 3 hours 9 minutes

from £68 / 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 £90 / night

£635 - £730 / week

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from £90 / night

(10) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from £100 / night

£695 - £827 / week

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from £100 / night

(3) Very Good 

81

Holiday home in Oak Island Harbor

Kissimmee / Oak Island Harbor

6 13 4 nights min

  • 6 bedrooms
  • Sleeps 13
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £197 / night

£1378 / week

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from £197 / night

(1)  

24

Holiday villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 3 nights min

  • 7 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Air conditioning

from £140 / night

£980 - £1295 / week

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from £140 / night

28

Legacy Dunes Resort holiday condo rental

Kissimmee / Legacy Dunes Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool

from £60 / night

£400 - £450 / week

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Responds fast!
avg. 3 hours 49 minutes

from £60 / night

(7) Very Good 

12

Holiday villa rental

Kissimmee / Lindfields

4 8 5 nights min

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

from £73 / night

£511 - £525 / week

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from £73 / night

(3) Excellent 

61

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
“Luxury in the sun” Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and easy run to NASA. Onsite centr
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from £115 / night

£690 - £1350 / week

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from £115 / night

23

Holiday home in Kissimmee

Central Florida / Kissimmee

7 16 Min stay varies

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

from £197 / night

£1378 - £2245 / week

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from £197 / night

(1) Very Good 

56

Holiday townhouse in Kissimmee City

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Great wee resort” Terra Verde was an immaculately kept resort. Seemed to be 20mins from most big attraction parks. This house was ideal for our family of four and could easily have accommodated 2 more. It was spotlessly clean and the couple of hiccups
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from £75 / night

£525 - £630 / week

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Responds fast!
avg. 2 hours 35 minutes

from £75 / night

(18) Very Good 

24

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent value, good facilities, close to the Disney Parks” The accommodation was excellent value for money. It was more than spacious enough for 2 adults and 2 children, and had good facilities (although it lacked wi-fi, which was sorely missed by s
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from £79 / night

£552 / week

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from £79 / night

30

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly

from £87 / night

£607 / week

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from £87 / night

(7) Excellent 

31

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Spacious villa with everything we needed” I stayed at this villa with my husband and 3 boys aged 13, 10 and 7yrs old. The property was very spacious with a double bedroom and bathroom downstairs which we used, leaving the boys to have loads of roo
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from £66 / night

£460 - £599 / week

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Responds fast!
avg. 1 hour 30 minutes

from £66 / night

24

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £239 / night

£874 - £2124 / week

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from £239 / night

18

Crescent Lakes holiday villa rental

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £102 / night

£709 - £867 / week

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from £102 / night

(21) Very Good 

24

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home from home.” The villa is in a fantastic location for all the attractions and the gated community is set in an attractive environment. The photos do not do it justice- we were blown away with the space and quality of this lovely villa. It has ho
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from £75 / night

£480 - £600 / week

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Responds fast!
avg. 3 hours 25 minutes

from £75 / night

(1) Very Good 

22

Holiday home in Kissimmee

Central Florida / Kissimmee

6 12 6 nights min

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

from £126 / night

£863 / week

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from £126 / night

30

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

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

from £99 / night

£662 - £784 / week

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from £99 / night

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • 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 £197 / night

£1378 / week

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from £197 / night

(3) Very Good 

14

Kissimmee holiday villa let

Kissimmee / Windsor Hills Resort

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly

from £182 / night

£1260 / week

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from £182 / night

25

Holiday villa in Kissimmee

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly

from £101 / night

£706 / week

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Responds fast!
avg. 2 hours 51 minutes

from £101 / night

(5) Very Good 

74

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

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

from £124 / night

£941 - £1099 / week

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Responds fast!
avg. 3 hours 58 minutes

from £124 / night

(4) Very Good 

12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Idyllic base for Orlando holiday” Just got back from this lovely villa where we spent a wonderful two weeks. The owners have made this feel just like home, with everything necessary for a comfortable stay. From the extended pool deck with comfy sunbed
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from £87 / night

£626 / week

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from £87 / night

10

Holiday home rental

Central Florida / Kissimmee

3 8 3 nights min

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

from £71 / night

£469 / week

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from £71 / night

15

Kissimmee holiday home accommodation

Kissimmee / Emerald Isle Kissimmee

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £71 / night

£481 / week

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from £71 / night

18

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

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

from £104 / night

£723 / week

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from £104 / night

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

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

from £114 / night

£793 / week

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from £114 / 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 £186 / night

£1182 - £1812 / week

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Responds fast!
avg. 52 minutes

from £186 / night

(7) Excellent 

25

Holiday home with shared pool in Kissimmee

Kissimmee / Lucaya Village

4 10 Min stay varies

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

from £91 / night

£764 / week

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Responds fast!
avg. 2 hours 4 minutes

from £91 / night

30

Home rental in Kissimmee

Central Florida / Kissimmee

4 4 Min stay varies

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

from £95 / night

£626 - £827 / week

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from £95 / 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
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from £107 / night

£745 / week

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from £107 / night

1