Air conditioned apartments and villas to rent in Kissimmee

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  • Florida
  • Central Florida
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Also consider

Emerald Isle Kissimmee
63 properties
Kissimmee City
38 properties
Villas Windsor Hills Resort
32 properties
Villas Paradise Palms
31 properties
Lake Berkley
29 properties
Villas Windsor Palms
25 properties
Lindfields
21 properties
Cumbrian Lakes
20 properties
Bellavida Resort
20 properties
Terra Verde Resort
20 properties
Villas Indian Creek
15 properties
Crescent Lakes
15 properties
Compass Bay
13 properties
Sunset Lakes
12 properties
Regal Oaks
12 properties
Venetian Bay Villages
12 properties
Seasons Resort
12 properties
Villas Formosa Gardens
11 properties
Eagle Pointe
10 properties
Encantada Resort
9 properties
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3,271 Holiday homes

Filters applied: Air conditioning (3,271)

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

(14) Excellent 

1 / 28

Villa Horizon - Sunset Lakes villa sleeps 12

Florida / Central Florida / Kissimmee / Sunset Lakes

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Villa Overview: Villa Horizon, located in the ideally situated community of Sunset Lakes, offers you and your party the unique opportunity to spend your Florida vacation in a quiet rural setting, yet only a short drive away from the theme parks, restaurants, shopping m  …see more

from £114 / night

£800 - £1050 / week

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from £114 / night

(27) Excellent 

1 / 20

PJ Sunshine Villa with secluded private pool

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Situated in a quiet, well established residential area our 5 bedroom villa easily accommodates 2 large families. There are 2 large master bedrooms with ensuites, 3 more bedrooms and a further bathroom. Outside space comprises a large private heated swimming pool with c  …see more

from £91 / night

£637 - £690 / week

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from £91 / night

(2) Excellent 

1 / 23

Bella Casa our luxury villa (hot tub, pool & wifi)

Florida / Central Florida / Kissimmee / Bellavida Resort

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Visit our owner website at the bottom of the page to view our 360 degree walk-through video: This is a a beautiful Mediterranean style property which has been designed, built and decorated to be the amongst the best. With 6 bedrooms and 5 1/2 bathrooms this is the per  …see more

from £165 / night

£1155 - £1435 / week

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from £165 / night

(1) Excellent 

1 / 25

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £135 / night

£850 - £1100 / week

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from £135 / night

1 / 40

Homely 4BR with 2 Master Suites, Kissimmee

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Ready to have your dream Florida vacation? You're gonna need a dream house!This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme privacy a  …see more

from £99 / night

£682 - £910 / week

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from £99 / night

(7) Very Good 

1 / 49

Serendipity Florida, Charming Getaway with Wireles

Florida / Central Florida / Kissimmee / Trafalgar Village

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Less than 15 miles from Walt Disney World, this villa offers a private backyard pool and hot tub (heated on request, fees payable). The 4-bedroom, 4 bathroomed house includes a fully equipped kitchen and spacious bedrooms with flat-screen TVs. Free Wi-Fi is available t  …see more

from £80 / night

£450 - £680 / week

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from £80 / night

1 / 39

Furnished 4 Bedroom Villa for rent, Villa Betty Bo

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s  …see more

from £76 / night

£500 - £652 / week

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from £76 / night

(1) Excellent 

1 / 30

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £106 / night

£791 / week

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from £106 / night

(3) Very Good 

1 / 12

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
 …see more

from £84 / night

£584 / week

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from £84 / night

1 / 24

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £107 / night

£637 - £1114 / week

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from £107 / night

1 / 90

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £95 / night

£637 - £743 / week

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from £95 / night

1 / 20

Lovely Pool Villa Near Disney - Emerald Isle Kissimmee villa sleeps 17

Florida / Central Florida / Kissimmee / Emerald Isle Kissimmee

8 bedroomsSleeps 17Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles to Universal Studio and has easy access to all major theme parks. This beautiful villa locates in the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate. This villa has 8 bedrooms 4.5 ba  …see more

from £266 / night

£1213 - £2416 / week

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from £266 / night

(4) Excellent 

1 / 55

Windsor Hills,own cinema room, Xbox one, free WiFi

Florida / Central Florida / Kissimmee / Windsor Hills Resort

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Our Villa in Windsor Hills is a BEAUTIFUL custom designed home. Windsor Hills is a secure gated community that has all the amenities of a 5 star hotel or resort, but with the comfort, convenience, and privacy of staying in a high end home. Facilities Air Conditioning F  …see more

from £171 / night

£0 / week

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from £171 / night

(4) Excellent 

1 / 12

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £103 / night

£716 - £1035 / week

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from £103 / night

1 / 52

Oak Island Cove Just 2 miles from Disney World

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Luxury house with private pool located just 2 miles from Disney World. Beautiful 3 bed /2 full bath - private screened swimming pool- Free Wi-Fi Furnished - Cable TV - Fully appointed kitchen - all linen and towels - located just 2 miles from Disney World Bedding: One  …see more

from £84 / night

£0 / week

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from £84 / night

(3) Excellent 

1 / 32

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £185 / night

£0 / week

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from £185 / night

(1) Excellent 

1 / 19

4 bed/3bath 5 mins from Disney - Indian Creek villa sleeps 10

Florida / Central Florida / Kissimmee / Indian Creek

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
This fantastic luxury, 4 bed 3 bath villa has just been totally redecorated to a high standard. With it's private, screened pool, removable child safety fence and large lanai - it's a perfect location to relax after a day at the theme parks or an 18 hole game  …see more

from £79 / night

£632 / week

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from £79 / night

1 / 35

Florida / Central Florida / Kissimmee

2 bedroomsSleeps 82 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Air conditioning;
 …see more

from £125 / night

£875 - £1088 / week

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from £125 / night

(1) Excellent 

1 / 59

Florida / Central Florida / Kissimmee

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £145 / night

£925 - £975 / week

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from £145 / night

1 / 20

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £75 / night

£0 / week

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from £75 / night

1 / 12

Florida / Central Florida / Kissimmee / Paradise Palms

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £186 / night

£1501 / week

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from £186 / night

(11) Very Good 

1 / 76

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 133 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £61 / night

£455 - £663 / week

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from £61 / night

(4) Excellent 

1 / 73

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; Pets welcome;
 …see more

from £98 / night

£662 - £768 / week

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from £98 / night

(3) Excellent 

1 / 24

Luce Del Sol Villa - Tuscany - Florida house sleeps 10

Florida / Central Florida / Kissimmee / Tuscany, Florida

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
This new luxurious Florida villa rental boasts beautiful décor and very high quality furnishings throughout. Surrounded by landscaped gardens, it is in the community of Tuscany at Westside, close to three golf courses including the award winning Highlands Reserve. The  …see more

from £115 / night

£805 - £980 / week

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from £115 / night

1 / 34

Florida / Central Florida / Kissimmee / Crescent Lakes

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £97 / night

£674 / week

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from £97 / night

1 / 57

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £182 / night

£1273 - £1867 / week

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from £182 / night

1 / 20

Florida / Central Florida / Kissimmee

1 bedroomSleeps 61 night min stay

  • 1 bedroom
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 105 km; Not suitable for children; Air conditioning;
 …see more

from £57 / night

£349 / week

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from £57 / night

1 / 39

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £91 / night

£637 - £1114 / week

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from £91 / night

(7) Excellent 

1 / 42

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £122 / night

£849 - £1008 / week

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from £122 / night

(4) Excellent 

1 / 26

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £91 / night

£637 - £985 / week

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from £91 / night

1 / 20

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £235 / night

£1639 - £2222 / week

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from £235 / night

(11) Excellent 

1 / 34

Funshine Magical Villa with Gameroom and WiFi

Florida / Central Florida / Kissimmee / Kissimmee City

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~ YOUR DREAM VACATION RENTAL IN THE SUNSHINE CAPITAL IS HERE ... COME AND ENJOY: A Beautiful Sun Drenched 4 bedroom 2 storey fully a  …see more

from £65 / night

£656 - £804 / week

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from £65 / night

1 / 25

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £227 / night

£1586 - £2116 / week

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from £227 / night

(1) Excellent 

1 / 21

Florida / Central Florida / Kissimmee / Encantada Resort

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £72 / night

£493 - £644 / week

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from £72 / night

1 / 30

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 126 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 6 nights min stay
Key info: Swimming pool; Not suitable for children; Car not necessary;
 …see more

from £114 / night

£796 - £849 / week

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from £114 / night

(2) Very Good 

1 / 38

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 72 km; Swimming pool;
 …see more

from £52 / night

£435 - £488 / week

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from £52 / night

(13) Excellent 

1 / 49

4 Bedroom Poolside Sunny Retreat with WiFi

Florida / Central Florida / Kissimmee / Eagle Pointe

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 60 km; Swimming pool;
Your beautiful vacation home is at Eagle Point, Kissimmee, one of the best possible locations for access to Orlando's famous theme parks, attractions and Golf Courses. When you stay in this executive pool home, you will get great views, great decor and a private locatio  …see more

from £80 / night

£493 - £625 / week

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from £80 / night

1 / 15

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £75 / night

£525 - £791 / week

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from £75 / night

1 / 35

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £204 / night

£1427 - £2222 / week

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from £204 / night

1 / 23

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £110 / night

£0 / week

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from £110 / night

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