Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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3,486 Holiday homes

Filters applied: Air conditioning

Travellers going to Kissimmee are booking March dates now. Secure your holiday home today and have the perfect trip.

(2) Very Good 

100

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Secret Key Cove Villa Luxury Award Winning Vacation villa rental, in Orlando, FloridaSet in a Gated CommunityThis 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. <br />Emer  …see more

from £112 / night

£784 - £1138 / week

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from £112 / night

12

Townhouse rental in Kissimmee

Kissimmee / Terra Verde Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
quiet resortUse of all Resort facilities  …see more

from £65 / night

£455 - £805 / week

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from £65 / 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
5 Bed, 3.5 Bath ~ Fabulous Vacation Home ~ Sleeps 12 guests + InfantsJust 5 mins drive from Walt Disney Private South Facing Pool with Beautiful Lake View ~ Quiet Location Yet Close To AmenitiesBright, Modern Villa in a Great LocationGreat for Families/group<br />  …see more

from £118 / night

£825 - £1090 / week

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from £118 / night

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are ideally located for the numerous Florida attractions including Disney, Universal Studios, and Seaworld. For golfers the townhouse is ideally located with many fantastic courses within easy reach, with the closest being Falcons Fire Golf Club and Celebration Golf  …see more

from £92 / night

£644 / week

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from £92 / night

(8) 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
“Our stay in Florida was made that much more enjoyable staying here” 995 Lake Berkley Drive, was a great place for us to stay during our recent two week trip to Florida. The estate itself is very impressive, clean and well maintained. A safe and secure  …see more

from £120 / night

£812 - £980 / week

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from £120 / night

84

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury family villa is situated within the well established, prestigious Lake Berkley Community, perfectly located just off the US 192, behind Medieval Times. This central, yet private location, within 10 minutes of Disney is also within strolling distance of the Wa  …see more

from £116 / night

£812 - £829 / week

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from £116 / night

(3) Excellent 

100

Kissimmee / Paradise Palms

4 12 Min stay varies

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

 …see more

from £96 / night

£672 / week

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from £96 / night

(2) Very Good 

59

Central Florida / Kissimmee

4 8 Min stay varies

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

 …see more

from £112 / night

£784 / week

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from £112 / night

(17) Excellent 

17

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 - £525 / week

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from £70 / night

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
THE VILLA FOR A LUXURY HOLIDAY! South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £150 / night

£1050 / week

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from £150 / night

19

Kissimmee / Indian Creek

4 8 4 nights min

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

 …see more

from £136 / night

£947 / week

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from £136 / 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  …see more

from £115 / night

£690 - £1350 / week

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from £115 / 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  …see more

from £112 / night

£784 / week

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from £112 / night

40

Central Florida / Kissimmee

5 12 2 nights min

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

 …see more

from £136 / night

£947 / week

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from £136 / night

(1) Excellent 

17

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
You will feel it the moment you pass the entry gates to this beautiful new community. A sense of peace and harmony with nature. Pleasing street-scapes are lined with ancient oak trees, giving shade as well as a taste of Florida's natural beauty. Sparkling lakes pro  …see more

from £129 / night

£900 / week

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from £129 / 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
Set in the beautiful Bellavida Resort with own South West Facing Pool. Close to all attractions including Disney World, Universal Studios and Islands of Adventure. Dining and Shops are in abundance.  …see more

from £108 / night

£748 / week

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from £108 / 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
Gated CommunityPlay AreaSoccer PitchesBicycle PathsClose to 192 with range of shops and restaurantsLake ViewSpaGames Room with pool table and football  …see more

from £120 / night

£840 - £1190 / week

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from £120 / night

(2) Excellent 

69

Villa rental in Kissimmee

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Excellent” Superb villa beautiful view of the lake really enjoyed our stay didn't want to come home! definitely recommend  …see more

from £90 / night

£630 - £840 / week

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from £90 / night

(4) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Perfect” This villa was excellent (exactly as advertised). The location was great being only 10-15 minutes from Walt Disney World. It was perfectly positioned for shopping too, Walmart was only a few minutes away. The kids loved their bedrooms and  …see more

from £80 / night

£560 - £835 / week

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from £80 / night

(1) Excellent 

18

Central Florida / Kissimmee

4 10 Min stay varies

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

 …see more

from £106 / night

£740 / week

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from £106 / night

(1) Excellent 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

(6) Excellent 

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
STUNNING 5 ***** LAKE VIEW ORLANDO VILLA Guests can relax and really enjoy this amazingly tranquil and peaceful setting EXCEPTIONAL LOCATION IN UNIQUE NATURAL CONSERVATION AREA WONDERFUL LAKE FRONT SPOT ..... SO PEACEFUL YET STILL CLOSE TO ALL THE AREA'S MAIN  …see more

from £130 / night

£840 - £1090 / week

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from £130 / 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
This lavishly decorated suite features a master bedroom with a king-size bed, flat screen TV and a Whirlpool tub for two. The living room has a queen sleeper sofa and a second flat screen TV with a stereo system and safety deposit box. Enjoy dinner in the dining room th  …see more

from £50 / night

£350 - £650 / week

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from £50 / night

(1) Excellent 

8

Holiday home in Kissimmee

Kissimmee / Lake Marion

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering condo with communal pool and free WiFi in the property, along with a full set of cable channels<br />Totally Renovated 2 Bed Family Home With Pool & Free Wi-Fi  …see more

from £35 / night

£250 / week

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from £35 / night

(11) Excellent 

23

Holiday villa in Hamilton's Reserve

Kissimmee / Hamilton's Reserve

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool
“Brilliant villa - perfect place for the perfect holiday” Stayed at the villa as part of a group of 4 adults and 4 children, aged from 4-9. Villa was everything we had hoped it would be and more. Photos did not do it justice. The size of the pla  …see more

from £98 / night

£685 - £1240 / week

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from £98 / night

(1) Excellent 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 3 bedroom 2 bathroom villa in Kissimmee. This villa has a private screened pool overlooking a lake. Situated in the tranquil community of Eagle Pointe only 15 minutes from Disney. Living Room – Light and airy open plan room overlooking the pool with two  …see more

from £86 / night

£600 - £750 / week

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from £86 / night

(7) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £85 / night

£560 - £665 / week

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from £85 / night

14

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This 4 Bedroom 3 Bathroom home, in the well sought after Terra Verde Resort ,in Kissimmee, is a very spacious villa. Ideal for two families to share as there are two Master Bedrooms and 2 sitting areas. The two twin bedrooms share a Jack and Jill bathroom.There is also  …see more

from £100 / night

£700 - £910 / week

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from £100 / night

(25) 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
“Very nice villa, exactly as advertised.” Thoroughly enjoyed our stay at Dolphin Villa. The villa is located in a secluded estate with large private garden to rear and no neighbours overlooking the pool deck. The villa is in good condition and we didn'  …see more

from £125 / night

£795 - £975 / week

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from £125 / night

30

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous location for everything the area has to offer. Only 10 minutes from Disney main gates & 20 mins to Universal. Convenient for shops, restaurants and outlets Complex offers heated pool, tennis, basketball, play area, splash pad, volley ball, & other amen  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

(10) Excellent 

20

Bellavida Resort holiday villa rental

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“5 star villa - everything you need for the holiday of a lifetime” This was our third visit to Orlando and was way beyond our expectations. The villa was amazing. Spacious, luxurious and well equipped with everything you need for a relaxing holiday.  …see more

from £160 / night

£1087 / week

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from £160 / night

(5) Very Good 

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful sunsets and a fabulous vacation home” We choose Star Lake View as we were looking for a nice lakeside view as we were not disappointed. The views of the sunset were gorgeous and we loved spotting all the wild birds. The villa was immacula  …see more

from £90 / night

£585 / week

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from £90 / night

17

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Family Fun in the Heart of Orlando, Florida. Shop, dine, play, golf—we've got everything you need for the vacation of a lifetime. And right next door to Walt Disney World® Resort and Animal Kingdom! Luxuriously decorated villas for your comfort.<br /&g  …see more

from £171 / night

£950 / week

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from £171 / night

(6) Excellent 

18

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent living in secure environment for family” Well equipped house for a family, from kitchen, over bedrooms and living area to pool, close to attractions, dining and shopping  …see more

from £100 / night

£695 - £750 / week

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from £100 / 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
6 beds, 4Bath with 3 master suites, new digital TV set in all bed rooms, a 60" TV in living room, Minutes to Disney World and shopping malls, A great place for family vacation with gated community & forest view. A Child high chair, 3 strollers are available on  …see more

from £128 / night

£904 - £1328 / week

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from £128 / 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
5 Bed, 3 Bath Luxury Villa, Pool, Spa, Games Room, Free In-House Wireless Internet - Emerald Island Resort. Ideal location,3 miles from Disney, one mile shops, Restaurants, mini golf, supermarkets and a medical centre. Internet streaming for Netflix etc Baby facilities  …see more

from £120 / night

£725 - £1120 / week

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from £120 / night

(1) Excellent 

18

Kissimmee holiday apartment rental

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Walk to shops, restaurants and supermarkets. We are 5 minutes from Disney and 20 minutes from Universal. Fully equipped kitchen and washer/dryer with free WIFI. Free parking.  …see more

from £80 / night

£560 / week

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from £80 / night

(2) Very Good 

13

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Amazing stay, great villa” Had a lovely stay for 2 weeks. Very easy to book and a lot of useful information emailed before and in the villa as well. Brilliant directions- made it a less daunting experience! Villa very clean with plenty of room and s  …see more

from £80 / night

£499 - £611 / week

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from £80 / night

(2) Excellent 

100

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
LUXURY OF THE HIGHEST QUALITY! Large South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £200 / night

£1400 / week

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from £200 / night

(8) Very Good 

60

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • 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  …see more

from £115 / night

£795 - £1330 / week

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from £115 / night