Air conditioned apartments and villas to rent in Kissimmee

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  • United States
  • Florida
  • Central Florida
  • Kissimmee

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  • Bass Lakes Estate (1)
  • Bellavida Resort (20)
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  • Crystal Cove Resort (5)
  • Cumbrian Lakes (23)
  • Doral Woods (9)
  • Eagle Pointe (10)
  • Emerald Isle Kissimmee (68)
  • Encantada Resort (9)
  • Fiesta Key (6)
  • Formosa Gardens (12)
  • Hamilton's Reserve (2)
  • Indian Creek (16)
  • Indian Point (3)
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  • Indian Ridge Oaks (5)
  • Kissimmee City (36)
  • Lake Berkley (28)
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  • Legacy Dunes Resort (6)
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  • Lindfields (22)
  • Lucaya Village (2)
  • Oak Island Cove (6)
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  • Orange Lake Resort (8)
  • Paradise Palms (31)
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  • Remington (2)
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  • Seasons Resort (13)
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  • Terra Verde Resort (19)
  • The Hamlets (3)
  • Trafalgar Village (8)
  • Tuscany, Florida (2)
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  • Westside (24)
  • Windsor Hills Resort (32)
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3,270 Holiday homes

Filters applied: Air conditioning (3,270)

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

1 / 26

Florida / Central Florida / Kissimmee

2 bedroomsSleeps 6Min stay varies

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

from £59 / night

£382 / week

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from £59 / night

(1) Excellent 

1 / 40

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £152 / night

£1064 - £1320 / week

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from £152 / night

(10) Very Good 

1 / 20

Gorgeous Vacation Home on Candy Palm Road in Kissimmee

Florida / Central Florida / Kissimmee / Paradise Palms

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful pool home. Attention to every detail has been put in as we furnished an  …see more

from £168 / night

£1176 - £2191 / week

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from £168 / night

1 / 25

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 124 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £111 / night

£0 / week

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from £111 / night

1 / 26

Florida / Central Florida / Kissimmee

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £152 / night

£1064 - £2138 / week

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from £152 / night

(21) Very Good 

1 / 17

Amazing Disney Condo, Pool & Hot tub Onsite

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 64 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Nearest beach 106 km; Swimming pool; Great for children of all ages ;
A perfect location for all that central Florida has to offer, for Mickey fans, serious shoppers, sun worshippers, delicious dining, space shuttle launches, big thrills and spills, airboat adventures, palm trees and pina-coladas! All in the fantastic Sunshine State! Win  …see more

from £35 / night

£220 - £330 / week

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from £35 / night

1 / 24

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £84 / night

£583 - £1010 / week

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from £84 / night

1 / 66

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
 …see more

from £96 / night

£618 - £668 / week

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from £96 / 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 £80 / night

£636 / week

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from £80 / night

(6) Excellent 

1 / 16

Celebration Villa, Vacation Home Pool and Spa

Florida / Central Florida / Kissimmee / Indian Creek

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Welcome to our beautiful 4 bedroom home right in the heart of the fun capital of Florida. Our home sleeps 8 people in perfect comfort and is ideal for large family get togethers or two-family getaways.Only 3.8 miles to Disney and 1 mile to shops and restaurants it'  …see more

from £100 / night

£770 - £800 / week

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from £100 / night

(4) Very Good 

1 / 22

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £88 / night

£584 - £1055 / week

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from £88 / night

(5) Excellent 

1 / 20

Relaxing Retreat in Kissimmee with Gameroom, Hot Tub, WiFi

Florida / Central Florida / Kissimmee / Emerald Isle Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 50 km; Swimming pool;
This home has it all !! *Newly installed Granite kitchen worktops* Our 3,400sqft beautifully decorated Villa is a Luxurious 5 star, 7 bedroom, 5 Bath home, a Private Screened-in South Facing Pool and Jacuzzi with a beautiful view over a lake and preserve (no homes behi  …see more

from £203 / night

£1417 - £2405 / week

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from £203 / night

1 / 12

Florida / Central Florida / Kissimmee

2 bedroomsSleeps 4Min stay varies

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

from £58 / night

£348 / week

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from £58 / night

(5) Excellent 

1 / 11

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 514 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 14 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £52 / night

£360 / week

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from £52 / 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 £107 / night

£797 / week

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from £107 / night

(15) Very Good 

1 / 66

Lovely Mango Keys Home includes WiFi and Hot Tub

Florida / Central Florida / Kissimmee / Lindfields

2 bedroomsSleeps 54 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 90 km; Swimming pool;
A WONDERFUL OPPORTUNITY TO ENJOY AN AMAZING VACATION IN THE SUNSHINE STATE OF FLORIDA.THE ACOMMODATION IS SITUATED IN A QUIET RESIDENTIAL AREA JUST 10 MINUTES DRIVE FROM ALL THE DISNEY ATTRACTIONS. THE TOWNHOUSE IS JUST OFF THE 192 IN KISSIMMEE AND JUST A SHORT DRIVE FR  …see more

from £50 / night

£350 / week

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from £50 / night

(5) Excellent 

1 / 22

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £123 / night

£840 - £1146 / week

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from £123 / night

1 / 30

Florida / Central Florida / Kissimmee / Lake Marion

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 126 km; Swimming pool;
 …see more

from £47 / night

£0 / week

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from £47 / night

(8) Very Good 

1 / 10

Florida Holiday Villa includes WiFi and Hot Tub

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 94 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Our villa is situated in the popular community of Indian Point, which is about 15 minutes drive from Disney and close to the other vast array of attractions that Florida has to offer. It is the perfect place to relax by the pool, or come back to after a day at the theme  …see more

from £65 / night

£450 / week

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from £65 / night

(1) Excellent 

1 / 20

Captain Hook's Haven in Paradise Palms Resort

Florida / Central Florida / Kissimmee / Paradise Palms

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
First floor consists of 892 sf with hallway, bathroom, king size bedroom, living room with dining area and a luxurious kitchen. Second floor has 888 sf including 3 bedrooms, 2 full bathrooms, washroom with washer and dryer and closet in the hallway for linens. The patio  …see more

from £77 / night

£497 - £855 / week

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from £77 / night

1 / 32

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 112 km; Swimming pool; Great for children of all ages ;
 …see more

from £97 / night

£640 - £913 / week

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from £97 / night

1 / 16

Luxury 4 bed town house close to Disney parks

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £88 / night

£0 / week

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from £88 / night

(8) Excellent 

1 / 35

Florida / Central Florida / Kissimmee / Venetian Bay Villages

3 bedroomsSleeps 83 nights min stay

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

from £58 / night

£344 - £413 / week

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from £58 / night

(14) Excellent 

1 / 93

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 £104 / night

£710 - £878 / week

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from £104 / night

(2) Excellent 

1 / 66

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 85 nights min stay

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

from £77 / night

£516 - £726 / week

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from £77 / night

1 / 17

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Suitable for children age 5+; Air conditioning; No pets allowed;
 …see more

from £85 / night

£589 - £794 / week

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from £85 / night

(2) Excellent 

1 / 14

Florida / Central Florida / Kissimmee / Trafalgar Village

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £69 / night

£459 - £764 / week

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from £69 / night

1 / 11

Florida / Central Florida / Kissimmee

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £115 / night

£802 / week

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from £115 / night

1 / 26

Florida / Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

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

from £100 / night

£802 - £913 / week

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from £100 / night

1 / 21

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 84 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Nearest beach 81 km; Swimming pool; Great for children of all ages ;
 …see more

from £73 / night

£531 - £668 / week

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from £73 / night

1 / 18

Florida / Central Florida / Kissimmee

6 bedroomsSleeps 11Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £123 / night

£855 - £1443 / week

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from £123 / night

1 / 24

Florida / Central Florida / Kissimmee

1 bedroomSleeps 4Min stay varies

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

from £92 / night

£657 - £817 / week

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from £92 / night

(4) Excellent 

1 / 15

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 £62 / night

£0 / week

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from £62 / 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 £111 / night

£0 / week

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from £111 / night

(9) Excellent 

1 / 24

Lovely Kissimmee Home with Gameroom and Pool

Florida / Central Florida / Kissimmee / Cumbrian Lakes

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
Our villa is situated just 10 minutes from Disney and all its attractions and 5 minutes to shops and restaurants.Private heated pool fully screened and safety fence.Open plan lounge and formal dining area Fully fitted kitchen making preparing meals and snacks a joy.King  …see more

from £70 / night

£480 - £595 / week

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from £70 / night

(6) Very Good 

1 / 35

Disney Dream,Outstanding villa with private pool

Florida / Central Florida / Kissimmee / Paradise Palms

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Our townhome is situated 10mins drive from Disney and 20mins from Universal.It is close to shops restraunts and the main theme parksOur home has 4 bedrooms 3 bathrooms,dining room/living room well equiped kitchen and heated pool.It is beside the Clubhouse only one minut  …see more

from £84 / night

£573 - £993 / week

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from £84 / night

(6) Excellent 

1 / 17

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 not necessary;
 …see more

from £104 / night

£726 - £955 / week

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from £104 / night

(2) Excellent 

1 / 69

Florida / Central Florida / Kissimmee

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £107 / night

£679 - £840 / week

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from £107 / night

(13) Excellent 

1 / 75

Florida / Central Florida / Kissimmee

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £77 / night

£535 - £642 / week

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from £77 / night

(10) Excellent 

1 / 69

Luxury Home near Disney and Golf Courses at Fiesta

Florida / Central Florida / Kissimmee / Fiesta Key

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Our lovely home is in the secure community "Fiesta Key", 15 mins. from Disney & Universal theme parks. Busch Gardens 1h 20m. Daytona Beach 1h 40m. Castillo de San Marcos, 2h 50m. South Beach Miami & Evergaldes, 3h 30m. Key West, 6h 30m. Kennedy Space Center, 1h 15m. Ame  …see more

from £31 / night

£340 - £378 / week

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from £31 / night

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