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Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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6,409 Vacation rentals

Kissimmee Vacation home rental

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $92 / night

$602 / week

1 / 26

Vacation villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $172 / night

$1,203 / week

1 / 29

Home rental in Kissimmee with indoor pool

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $138 / night

$962 / week

1 / 29

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $202 / night

$1,083 - $1,184 / week

1 / 47

Kissimmee Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $367 / night

$2,565 / week

1 / 13

Vacation home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,718 / week

1 / 13

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $137 / night

$954 / week

1 / 14

Vacation home with swimming pool in Oak Island Cove

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $155 / night

$1,082 / week

1 / 24

Vacation villa with golf nearby in Cumbrian Lakes

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $137 / night

$960 / week

1 / 21

Vacation home in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $184 / night

$1,145 / week

1 / 11

Vacation villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $115 / night

$802 / week

1 / 73

Vacation condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $136 / night

$653 / week

1 / 23

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 28

from $343 / night

$2,397 / week

1 / 45

Vacation apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $138 / night

$1,145 / week

1 / 8

Vacation townhouse in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $252 / night

$1,661 / week

1 / 21

Kissimmee Vacation apartment rental

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $98 / night

$682 / week

1 / 58

Vacation villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $202 / night

$1,415 / week

1 / 25

Vacation villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $207 / night

$1,432 - $3,206 / week

1 / 47

Vacation apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $125 / night

$800 / week

1 / 70

Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $173 / night

$1,211 / week

1 / 41

Kissimmee Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $138 / night

$962 / week

1 / 24

Townhouse rental in Kissimmee with swimming pool

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $83 / night

$577 / week

1 / 24

Vacation apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $108 / night

$756 / week

1 / 13

Vacation apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $82 / night

$573 / week

1 / 5

Vacation condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $115 / night

$802 / week

1 / 25

Vacation townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $205 / night

$1,435 / week

1 / 59

Kissimmee Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $344 / night

$2,405 - $2,685 / week

1 / 15

Kissimmee Vacation villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from $189 / night

$1,145 - $1,466 / week

1 / 68

Kissimmee Vacation villa rental

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from $368 / night

$2,573 / week

1 / 82

Vacation home rental

Kissimmee house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from $243 / night

$1,700 / week

1 / 37

Kissimmee Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $121 / night

$836 / week

1 / 40

Vacation apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $98 / night

$682 / week

1 / 13

Vacation home rental

Kissimmee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $238 / night

$1,661 / week

1 / 4

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 30

from $411 / night

$2,878 / week

1 / 46

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 30

from $343 / night

$2,397 / week

1 / 59

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 29

from $343 / night

$2,397 / week

1 / 50

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 25

from $572 / night

$4,000 / week

1 / 7

Vacation home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 29

from $686 / night

$4,801 / week

1 / 60

Kissimmee Vacation villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $89 / night

$618 / week

1 / 14

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 27

from $154 / night

$1,074 / week

1 / 89

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