Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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3,815 Holiday homes

Filters applied: Air conditioning

(20) Excellent 

25

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
“Perfect Florida home” From the minute we arrived, we loved and enjoyed every minute of our four week stay here. Everything was perfect from the moment we went through the door. The rooms are spacious, comfortable and tastefully decorated. Ove
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from £130 / night

£875 / week

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from £130 / night

(9) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Villa” This was our sixth time in Florida and our third stay at Doral Woods in our third different villa on the estate and it certainly compares very favourably in what is simply a very nice place to stay. Set in a very quiet residential cul
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from £80 / night

£560 - £930 / week

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from £80 / night

(6) Excellent 

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

from £130 / night

£840 - £1058 / week

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from £130 / night

(1) Excellent 

20

Villa rental in Cumbrian Lakes with swimming pool

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

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

from £105 / night

£735 - £1050 / week

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from £105 / night

(2) Excellent 

70

Holiday villa letting

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool

from £95 / night

£665 - £875 / week

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from £95 / night

(28) Excellent 

20

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
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from £83 / night

£575 - £625 / week

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from £83 / night

(2) Average 

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £172 / night

£1204 / week

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from £172 / night

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

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

from £86 / night

£597 / week

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from £86 / night

(12) Excellent 

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
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from £78 / night

£542 / week

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from £78 / night

(15) Excellent 

29

Kissimmee holiday villa rental

Kissimmee / Seasons Resort

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
“Excellent” Brilliant home. Well equipped. Great pool deck and jacuzzi. We got the sun all day and found the pool deck very private. The covered patio is good for shade. The location was perfect as close to all the attractions. Good restaurants c
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from £98 / night

£661 - £911 / week

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from £98 / night

(12) Very Good 

24

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa for families” We stayed at this villa with our daughter and my wife's parents. This is a fantastic property for more than one family as there are two master suites as well as a queen room and two twin bedrooms. The best feature is the exte
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from £100 / night

£550 - £700 / week

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from £100 / night

(13) Excellent 

44

Holiday villa rental

Kissimmee / Indian Ridge Oaks

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Close to Disney, a villa that caters for everyone!” We stayed here with our 8 year old in July 2016. From the time we booked to the time we returned Tracey (the owner) could not have been more helpful. Emails responded to promptly, very thoughtful
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from £75 / night

£520 - £780 / week

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from £75 / night

(31) Excellent 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic! Didn't want to leave!” The best vacation, my family ever had. Two small children ages 6yrs. and 4yrs. loved the kiddie pool.
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from £98 / night

£665 - £719 / week

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from £98 / night

(7) Very Good 

26

Kissimmee holiday villa rental

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great Disney Vacation” The house was great but does need some repairs. The ironing board could not be used the leg was broken in half. The living room furniture is very worn and needs to be replaced and when my husband went to open the refrigerator d
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from £71 / night

£493 / week

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from £71 / night

(7) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Fabulous home away from home” Ten of us stayed in this Villa, consisting 3 children, 2 teenagers and 5 adults. We had plenty of room for all of us as it's such a large property. The Villa was very well equipped with everything we needed and spotlessly
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from £118 / night

£903 / week

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from £118 / night

23

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £105 / night

£784 - £994 / week

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from £105 / night

(38) Excellent 

39

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t
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from £85 / night

£505 - £515 / week

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from £85 / night

(7) Excellent 

25

Kissimmee / Lucaya Village

4 10 Min stay varies

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

from £78 / night

£758 / week

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from £78 / night

(21) Excellent 

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great villa, everything you need” Villa was spacious, immaculately clean and had everything you could possibly need. Pool kept kids more than occupied, fun gator spotting in the lake behind the house. Easy to get to the main routes to head off to park
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from £107 / night

£750 - £900 / week

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from £107 / night

(20) Very Good 

18

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“I would return to this villa anytime” location was great, attractions within easy reach, restaurants and shops within easy reach, very clean villa with plenty of everything, pool was clean and inviting, loved it.
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from £65 / night

£450 - £500 / week

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from £65 / night

(14) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Lovely villa, great service and excellent location for all the Disney parks!” Definitely recommended! From the moment I enquired about the villa, (we dealt directly with the owner) we received excellent service. Booking was easy, and we were supplie
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from £90 / night

£580 - £775 / week

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from £90 / 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

(5) Excellent 

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Pete and Louise” I felt like I was at home !!!!! Everything I needed and could have forgotten was already there......this place was immaculate! It was close tho so many things to do and shopping as well......I will be back again real soon for sure, th
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from £50 / night

£308 - £325 / week

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from £50 / night

(36) Excellent 

62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Mrs” EXCELLENT...doesn't do it justice. Great location Great accommodation Great facilities Would have liked to have stayed longer. A lot of thought and care has gone into making this your home for your stay. Disney is easy to access.... food shops
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from £80 / night

£550 - £675 / week

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from £80 / night

(5) Very Good 

74

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 3 nights min

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

from £123 / night

£859 / week

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from £123 / night

(6) Very Good 

34

Townhouse rental in Paradise Palms with indoor pool, golf nearby

Kissimmee / Paradise Palms

4 8 Min stay varies

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

from £71 / night

£469 - £782 / week

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from £71 / 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 £118 / night

£821 / week

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from £118 / night

(7) Excellent 

18

Condo rental in Kissimmee

Central Florida / Kissimmee

3 8 1 night min

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

from £117 / night

£774 / week

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from £117 / night

(7) Very Good 

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Would recommend” Beautiful home, my family and I enjoyed every bit of it. Very spacious, listed as 4 bedrooms also has a loft so it's more like 5, we had a whole room we never used and everyone was comfortable. In a great area for shopping markets and
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from £102 / night

£704 / week

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from £102 / night

(22) Excellent 

24

Holiday townhouse rental

Kissimmee / Encantada Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Really nice” Nice house good location, we really liked the option of being able to use the pool at the house or the two large pools by the clubhouse. Would certainly stay again.
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from £100 / night

£680 - £950 / week

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from £100 / night

(3) Very Good 

28

Holiday villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £90 / night

£606 - £739 / week

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from £90 / night

(13) Very Good 

55

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“fabulous house in great location with super pool area” this is a great property very well maintained and furnished to a high standard. it is in a great location..only 10 - 15mins from disney and 20 mins from universal. the communal pool and jacuzzi ar
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from £70 / night

£490 - £560 / week

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from £70 / night

(9) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £133 / night

£925 - £1195 / week

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from £133 / night

(10) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa” Was very impressed with the villa. Very spacious and clean. Lots of local amenities and all parks very close by. Situated on a quiet estate and very welcoming would definitely recommend
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from £85 / night

£520 - £680 / week

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from £85 / night

(4) Very Good 

18

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Superb villa” The only fault with this property is that we couldn't stay longer. The booking process went smoothly. The owner was very attentive and answered all of our questions promptly. The villa is in a perfect setting and is fully equipped, clean
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from £90 / night

£575 / week

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from £90 / 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 

75

Kissimmee holiday villa let

Kissimmee / Cumbrian Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £85 / night

£595 - £945 / week

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from £85 / night

(18) 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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from £75 / night

(37) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20
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from £99 / night

£675 / week

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from £99 / night

(26) Very Good 

56

Holiday home rental

Kissimmee / Lindfields

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 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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from £50 / night

£350 / week

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from £50 / night

1