Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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4,156 Holiday homes

Filters applied: Air conditioning

(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

(2) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th
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from £94 / night

£657 / week

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from £94 / 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 £153 / night

£1067 / week

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from £153 / night

(2) Excellent 

24

Holiday villa in Sunset Lakes

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fabulous villa in fabulous location” Stayed at this villa in September and had a wonderful time. The whole family thoroughly enjoyed themselves and the kids were in the pool virtually every day. The villa overlooks a lake and there are great sunsets.
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from £84 / night

£525 - £695 / week

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from £84 / night

(6) Excellent 

44

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very nice villa in a quiet and peaceful area.” The villa was very tidy and well maintained. The location was excellent, being very close to a supermarket and to Kissimmee. It was also an ideal location for all the excellent theme parks. We certainly w
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from £95 / night

£595 / week

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Responds fast!
avg. 2 hours 23 minutes

from £95 / 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

£728 / week

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from £104 / night

(8) Very Good 

37

Terra Verde Resort holiday home rental

Kissimmee / Terra Verde Resort

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

from £63 / night

£493 / week

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from £63 / night

(3) Excellent 

100

Holiday home in Kissimmee

Kissimmee / Paradise Palms

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

from £95 / night

£662 / week

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Responds fast!
avg. 3 hours 15 minutes

from £95 / 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 £58 / night

£400 / week

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Responds fast!
avg. 3 hours 57 minutes

from £58 / night

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 3 nights min

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

from £120 / night

£825 / week

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from £120 / night

(3) Very Good 

92

Cumbrian Lakes holiday home rental

Kissimmee / Cumbrian Lakes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“This place is amazing” We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the parks, lovely area and amazing view of the sunse
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from £195 / night

£1365 / week

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from £195 / 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 £72 / night

£485 / week

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from £72 / night

(1) Very Good 

20

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 105 km
  • Swimming pool
“Clean & Comfortable Family Friendly Villa” We thoroughly enjoyed our stay at this villa and found it to be well equipped and in a great position. It was easy to travel to any of the main attractions and has tons of shops and restaurants on its doorste
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from £112 / night

£778 / week

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Responds fast!
avg. 3 hours 39 minutes

from £112 / 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
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from £199 / night

£1389 / week

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from £199 / night

(3) Very Good 

15

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

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

from £72 / night

£500 - £630 / week

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from £72 / night

(10) 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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Responds fast!
avg. 3 hours 25 minutes

from £65 / 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

(3) Excellent 

16

Holiday villa in Indian Creek

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Great Florida Villa in a Perfect Location” Myself & my Family spent a lot of time looking on website at Villas for our Florida Holiday, hoping to find a Good deal with the right location near to all the Attractions and a villa that would be suitabl
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from £120 / night

£834 / week

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Responds fast!
avg. 1 hour 31 minutes

from £120 / 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 £72 / night

£556 / week

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from £72 / night

(1) Excellent 

17

Holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

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

from £120 / night

£725 - £1120 / week

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Responds fast!
avg. 1 hour 15 minutes

from £120 / night

38

Holiday home in Kissimmee

Kissimmee / Compass Bay

4 10 3 nights min

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

from £84 / night

£794 / week

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from £84 / night

(13) Excellent 

Certificate of Excellence

32

Holiday home with swimming pool in Paradise Palms

Kissimmee / Paradise Palms

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 141 km
  • Swimming pool
  • Child friendly
“Wonderful vacation” The house was beautiful, clean and very well-kept. Plenty of bedroom space, beautiful bathrooms, ample linens and towels supplied. We especially enjoyed the patio area at the pool. We spent many hours there, reading, relaxing and v
…see more

Certificate of Excellence

from £108 / night

£917 / 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

(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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Responds fast!
avg. 3 hours 32 minutes

from £118 / 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 £127 / night

£912 - £1317 / week

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Responds fast!
avg. 3 hours 43 minutes

from £127 / night

81

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £130 / night

£910 - £1190 / week

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Responds fast!
avg. 1 hour 30 minutes

from £130 / 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

(27) Very Good 

Certificate of Excellence

56

Holiday home rental

Kissimmee / Lindfields

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.
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Certificate of Excellence

from £50 / night

£350 / week

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Responds fast!
avg. 3 hours 25 minutes

from £50 / night

(9) Excellent 

37

Holiday home rental

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £70 / night

£450 - £660 / week

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Responds fast!
avg. 2 hours 17 minutes

from £70 / night

(4) Very Good 

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

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

from £110 / night

£770 - £1050 / week

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Responds fast!
avg. 1 hour 1 minutes

from £110 / night

(18) Excellent 

21

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

(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

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 £58 / night

£406 / week

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from £58 / night

(2) Excellent 

50

Holiday home with indoor pool in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

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

from £76 / night

£528 / week

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Responds fast!
avg. 2 hours 45 minutes

from £76 / night

(1) Very Good 

39

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 13 4 nights min

  • 6 bedrooms
  • Sleeps 13
  • 4 nights min
  • Nearest beach 144 km
  • Swimming pool
  • Child friendly

from £150 / night

£1050 / week

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from £150 / 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

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.
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from £130 / night

£840 - £1450 / week

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from £130 / night

26

Holiday townhouse with shared pool in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

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

from £65 / night

£455 - £628 / week

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from £65 / 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

15

Holiday villa rental

Central Florida / Kissimmee

8 20 4 nights min

  • 8 bedrooms
  • Sleeps 20
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £265 / night

£1855 / week

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Responds fast!
avg. 3 hours 20 minutes

from £265 / night

1