Air conditioned apartments and villas to rent in Kissimmee

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  • Kissimmee

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  • Bass Lakes Estate (1)
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  • Crystal Cove Resort (5)
  • Cumbrian Lakes (22)
  • Doral Woods (9)
  • Eagle Pointe (11)
  • Emerald Isle Kissimmee (66)
  • Encantada Resort (9)
  • Fiesta Key (6)
  • Formosa Gardens (14)
  • Hamilton's Reserve (2)
  • Indian Creek (16)
  • Indian Point (3)
  • Indian Ridge (5)
  • Indian Ridge Oaks (6)
  • Kissimmee City (36)
  • Lake Berkley (26)
  • Lake Marion (3)
  • Legacy Dunes Resort (6)
  • Liberty Village (5)
  • 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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  • Villasol (5)
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  • Windsor Hills Resort (34)
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Emerald Isle Kissimmee
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Seasons Resort
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Bellavida Resort
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Cumbrian Lakes
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Lindfields
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Terra Verde Resort
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Crescent Lakes
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Villas Indian Creek
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Compass Bay
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Villas Formosa Gardens
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Sunset Lakes
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Regal Oaks
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Venetian Bay Villages
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Eagle Pointe
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4,153 Holiday homes

Filters applied: Air conditioning (4,153)

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

(2) Excellent 

1 / 27

Holiday villa in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $227 / night

$1707 - $2820 / week

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from $227 / night

(7) Very Good 

1 / 24

Holiday home in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $147 / night

$956 - $1456 / week

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from $147 / night

1 / 40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $130 / night

$901 - $1201 / week

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from $130 / night

1 / 75

Kissimmee holiday home rental

Central Florida / Kissimmee

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $270 / night

$1801 - $2600 / week

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from $270 / night

(4) Very Good 

1 / 21

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 bedroomsSleeps 125 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min stay

from $127 / night

$889 - $1058 / week

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from $127 / night

(7) Excellent 

1 / 48

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $242 / night

$1707 - $2820 / week

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from $242 / night

(16) Excellent 

1 / 59

Holiday townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $125 / night

$559 / week

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from $125 / night

(11) Very Good 

1 / 18

Kissimmee holiday home let

Central Florida / Kissimmee

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $86 / night

$529 / week

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from $86 / night

(1) Excellent 

1 / 14

Kissimmee holiday townhouse rental

Kissimmee / Trafalgar Village

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $91 / night

$605 - $1209 / week

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from $91 / night

(1) Excellent 

1 / 44

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $162 / night

$1058 - $1712 / week

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from $162 / night

1 / 18

Kissimmee holiday home rental

Central Florida / Kissimmee

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies

from $202 / night

$1309 - $1712 / week

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from $202 / night

(1) Excellent 

1 / 25

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from $199 / night

$1250 - $1617 / week

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from $199 / night

(7) Excellent 

1 / 34

Holiday home with golf nearby in Encantada Resort

Kissimmee / Encantada Resort

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $80 / night

$554 - $1118 / week

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from $80 / night

1 / 49

Holiday home in Kissimmee

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $162 / night

$1006 - $1209 / week

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from $162 / night

1 / 17

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

8 bedroomsSleeps 20Min stay varies

  • 8 bedrooms
  • Sleeps 20
  • Min stay varies

from $201 / night

$1308 - $2819 / week

Book Book View

from $201 / night

1 / 21

Kissimmee holiday townhouse rental

Central Florida / Kissimmee

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $140 / night

$0 / week

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from $140 / night

(1) Excellent 

1 / 22

Holiday home in Kissimmee

Kissimmee / Crescent Lakes

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay

from $123 / night

$856 / week

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from $123 / night

1 / 16

Tower rental in Kissimmee with shared pool

Central Florida / Kissimmee

2 bedroomsSleeps 82 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $181 / night

$1410 / week

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from $181 / night

(2) Good 

1 / 31

Holiday apartment with shared pool in Kissimmee

Kissimmee / Kissimmee City

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $61 / night

$0 / week

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from $61 / night

1 / 23

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay

from $184 / night

$1287 - $1801 / week

Book Book View

from $184 / night

(4) Very Good 

1 / 18

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $133 / night

$846 - $1140 / week

Book Book View

from $133 / night

1 / 28

Kissimmee holiday home rental

Central Florida / Kissimmee

4 bedroomsSleeps 96 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 6 nights min stay

from $131 / night

$0 / week

Book Book View

from $131 / night

(4) Very Good 

1 / 12

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 bedroomsSleeps 85 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay

from $111 / night

$772 - $875 / week

Book Book View

from $111 / night

1 / 31

Kissimmee holiday home rental

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $343 / night

$2291 - $2996 / week

Book Book View

from $343 / night

1 / 39

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 bedroomsSleeps 13Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies

from $243 / night

$2205 / week

Book Book View

from $243 / night

(3) Very Good 

1 / 48

Holiday villa with golf nearby in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $46 / night

$798 - $1410 / week

Book Book View

from $46 / night

1 / 30

Holiday condo in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from $100 / night

$680 / week

Book Book View

from $100 / night

1 / 18

Holiday villa in Kissimmee

Central Florida / Kissimmee

6 bedroomsSleeps 11Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies

from $161 / night

$1121 - $1890 / week

Book Book View

from $161 / night

(3) Excellent 

1 / 15

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $89 / night

$625 - $758 / week

Book Book View

from $89 / night

1 / 17

Kissimmee holiday condo rental

Kissimmee / Kissimmee City

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $353 / night

$1259 / week

Book Book View

from $353 / night

(6) Very Good 

1 / 24

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $69 / night

$480 - $649 / week

Book Book View

from $69 / night

(1) Excellent 

1 / 20

Kissimmee holiday townhouse accommodation

Kissimmee / Paradise Palms

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $101 / night

$655 - $1128 / week

Book Book View

from $101 / night

(1) Excellent 

1 / 22

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $91 / night

$0 / week

Book Book View

from $91 / night

1 / 30

Holiday home rental

Central Florida / Kissimmee

7 bedroomsSleeps 165 nights min stay

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min stay

from $291 / night

$2000 - $2500 / week

Book Book View

from $291 / night

1 / 36

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $110 / night

$0 / week

Book Book View

from $110 / night

(5) Excellent 

1 / 53

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $136 / night

$902 - $972 / week

Book Book View

from $136 / night

(2) Very Good 

1 / 75

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 bedroomsSleeps 102 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $151 / night

$0 / week

Book Book View

from $151 / night

1 / 24

Holiday villa in Kissimmee

Central Florida / Kissimmee

7 bedroomsSleeps 18Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies

from $187 / night

$1209 - $2719 / week

Book Book View

from $187 / night

(1) Excellent 

1 / 100

Kissimmee holiday home rental

Central Florida / Kissimmee

7 bedroomsSleeps 16Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies

from $217 / night

$1586 - $3172 / week

Book Book View

from $217 / night

(3) Excellent 

1 / 51

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 bedroomsSleeps 73 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min stay

from $101 / night

$705 / week

Book Book View

from $101 / night

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