Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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4,450 Holiday homes

Filters applied: Air conditioning

(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
…see more

from £75 / night

£525 - £910 / week

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from £75 / night

(21) Very Good 

68

Holiday villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thanks” This was a great Vila with everything you needed and in a good area to base yourself, if any c ok militants a bit dated
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from £100 / night

£450 - £540 / week

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Responds fast!
avg. 2 hours 48 minutes

from £100 / night

(14) Excellent 

Certificate of Excellence

28

Doral Woods holiday villa rental

Kissimmee / Doral Woods

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect for couples and families” I stayed here for 9 days with my husband and 5 month old daughter and we had lovely time! My husband and I had previously been to Florida and stayed in a property in Doral Woods so we knew we wanted to be in the same
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Certificate of Excellence

from £65 / night

£460 - £480 / week

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Responds fast!
avg. 1 hour 31 minutes

from £65 / 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
…see more

from £70 / night

£465 - £595 / week

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from £70 / night

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 1 night min

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

from £95 / night

£662 / week

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from £95 / night

(4) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £50 / night

£350 / week

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from £50 / night

(28) Excellent 

23

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect size condo and fantastic location. Very clean with all you could need.” Brilliant location close to parks shirt drive away, shops walking distance and short drive to large supermarkets and amenities! Spacious and clean condo with everything yo
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from £65 / night

£455 / week

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Responds fast!
avg. 2 hours 14 minutes

from £65 / night

16

Legacy Dunes Resort holiday condo rental

Kissimmee / Legacy Dunes Resort

4 8 Min stay varies

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

from £99 / night

£475 - £950 / week

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Responds fast!
avg. 2 hours 9 minutes

from £99 / night

(11) Very Good 

70

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

(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

(3) Excellent 

30

Kissimmee holiday home rental

Central Florida / Kissimmee

3 8 Min stay varies

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

from £71 / night

£473 - £827 / week

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from £71 / 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
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from £107 / night

£682 - £808 / week

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Responds fast!
avg. 1 hour 14 minutes

from £107 / night

(27) Excellent 

56

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“On the booking with Steve” Steve has kindly been answering my questions and helped me make my decision to want to stay at his beautiful villa looks stunning
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from £125 / night

£825 - £995 / week

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Responds fast!
avg. 1 hour 25 minutes

from £125 / 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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from £65 / night

(9) Excellent 

36

Holiday home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £80 / night

£475 - £745 / week

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from £80 / 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 £53 / night

£371 / week

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from £53 / night

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,
…see more

from £157 / night

£1097 / week

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Responds fast!
avg. 3 hours 38 minutes

from £157 / night

29

Kissimmee holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

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

from £111 / night

£729 - £1020 / week

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from £111 / night

(9) Very Good 

24

Holiday home in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Fabulous House, Fabulous Holiday” We loved this house!!! It was spotlessly clean, and the furnishings were of a high standard. The beds were really comfy and the children loved the playroom and pool. Great for two families. It is a great location
…see more

from £61 / night

£427 / week

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from £61 / night

(23) Very Good 

Certificate of Excellence

10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £65 / night

£450 / week

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Responds fast!
avg. 1 hour 34 minutes

from £65 / night

(7) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

(30) Excellent 

Certificate of Excellence

21

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Mrs” Just back from a 2 week stay at this villa. It is one of the best we have stayed in. Perfect location, near lots of our favourite restaurants, disney etc. The pool gets sun all day and has loads of outdoor space. The pool and Jacuzzi heat actuall
…see more

Certificate of Excellence

from £83 / night

£575 - £625 / week

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Responds fast!
avg. 1 hour 18 minutes

from £83 / 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
…see more

from £119 / night

£827 / week

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Responds fast!
avg. 1 hour 31 minutes

from £119 / night

(29) Excellent 

24

Villa rental in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Brilliant stay loved this villa 5☆☆” When we arrived after a long flight we were welcomed with a beautiful villa,in a gated community so easy to find and looks amazing, everything was clean and the kitchen had had new appliances which look brilliant
…see more

from £110 / night

£750 - £900 / week

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from £110 / night

(6) Excellent 

Certificate of Excellence

48

Apartment rental in Kissimmee with shared pool

Central Florida / Kissimmee

3 6 3 nights min

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

Certificate of Excellence

from £67 / night

£469 - £552 / week

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Responds fast!
avg. 3 hours 31 minutes

from £67 / night

(12) Very Good 

62

Coral Cay holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“A Nice Stay!!!!” We really loved it and we wish if we would have stayed. Beautiful scenic, nice backyard overlooking the lake. The pool was nice with a hot pool
…see more

from £59 / night

£413 / week

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Responds fast!
avg. 3 hours 30 minutes

from £59 / night

(2) Excellent 

29

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £118 / night

£826 - £1481 / week

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from £118 / night

(13) Excellent 

Certificate of Excellence

22

Kissimmee holiday villa let

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super Villa in a super location,” A perfect location for us just a couple of minutes from Kissimmee, Everything you need is there, pool, hot tub, games room, WiFi and as it's English owned it even has a kettle ! (Most Florida Villas don't). Clear i
…see more

Certificate of Excellence

from £86 / night

£601 / week

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Responds fast!
avg. 3 hours 53 minutes

from £86 / night

(2) Very Good 

51

Holiday villa in Kissimmee

Kissimmee / Hamilton's Reserve

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 85 km
  • Swimming pool

from £119 / night

£729 - £827 / week

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from £119 / night

(6) Excellent 

Certificate of Excellence

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Great rental” Everything was very nice.. The owners are very considerate and everything is as stated. Very comfortable great pool very private. Close to Disney and everything ! Great for a family Thanks Chris and Elaine!
…see more

Certificate of Excellence

from £70 / night

£445 - £595 / week

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Responds fast!
avg. 1 hour 51 minutes

from £70 / 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 £95 / night

£670 - £768 / week

Enquire View

from £95 / night

(6) Very Good 

45

Holiday villa rental

Central Florida / Kissimmee

4 8 4 nights min

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

from £92 / night

£580 - £705 / week

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Responds fast!
avg. 3 hours 5 minutes

from £92 / 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

(18) Excellent 

48

Townhouse rental in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
“Absolutely fabulous -we will rent this villa again next time we go to Forida” There really wasn't anything about this property that disappointed us. It was clean, beautifully decorated and furnished, kitchen had more equipment that we ever used - an
…see more

from £65 / night

£400 - £525 / week

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Responds fast!
avg. 2 hours 6 minutes

from £65 / 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
…see more

from £95 / night

£595 / week

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Responds fast!
avg. 2 hours 23 minutes

from £95 / night

(10) Very Good 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £75 / night

£525 - £735 / week

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from £75 / night

(2) Excellent 

23

Holiday townhouse with golf nearby in Kissimmee

Kissimmee / Fiesta Key

3 8 Min stay varies

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

from £63 / night

£418 - £528 / week

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Responds fast!
avg. 1 hour 38 minutes

from £63 / night

(2) 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 £111 / night

£772 - £1120 / week

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from £111 / 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

(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

1