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Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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1,685 Vacation rentals

Vacation home with swimming pool in Oak Island Cove

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $152 / night

$1,059 / week

1 / 24

Vacation condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $106 / night

$741 / week

1 / 20

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $191 / night

$917 - $1,129 / week

1 / 46

Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $173 / night

$1,371 / week

1 / 37

Vacation villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $163 / night

$1,136 / week

1 / 37

Kissimmee Vacation home rental

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $92 / night

$602 / week

1 / 26

Kissimmee Vacation home rental

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from $310 / night

$2,164 / week

1 / 37

Vacation villa with golf nearby in Cumbrian Lakes

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $126 / night

$879 / week

1 / 21

Vacation villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $195 / night

$2,806 / week

1 / 36

Kissimmee Vacation villa accommodation

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $264 / night

$1,844 / week

1 / 38

Kissimmee Vacation villa rental

Kissimmee villa

  • 13 bedrooms
  • 10 bathrooms
  • sleeps 28

from $731 / night

$5,114 / week

1 / 37

Vacation villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $138 / night

$790 / week

1 / 4

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $212 / night

$988 / week

1 / 22

Kissimmee Vacation villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from $132 / night

$859 - $1,260 / week

1 / 70

Vacation townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $247 / night

$1,059 - $1,129 / week

1 / 90

Vacation home rental

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from $134 / night

$840 - $1,087 / week

1 / 40

Vacation villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $172 / night

$1,203 / week

1 / 43

Vacation villa in Kissimmee

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $100 / night

$774 / week

1 / 53

Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $134 / night

$939 / week

1 / 46

Vacation villa in Doral Woods

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $201 / night

$1,404 - $1,800 / week

1 / 24

Vacation apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from $138 / night

$1,002 / week

1 / 13

Vacation home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $184 / night

$1,283 / week

1 / 38

Vacation home in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $172 / night

$1,203 / week

1 / 50

Vacation home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,718 / week

1 / 13

Home rental in Kissimmee with shared pool

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $86 / night

$516 - $962 / week

1 / 19

Vacation villa in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

from $275 / night

$1,924 / week

1 / 51

Vacation villa rental

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from $304 / night

$2,124 / week

1 / 78

Vacation villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $242 / night

$1,693 - $2,089 / week

1 / 18

Kissimmee Vacation townhouse rental

Kissimmee townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $377 / night

$2,290 / week

1 / 5

Kissimmee Vacation apartment rental

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $98 / night

$682 / week

1 / 58

Vacation home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $161 / night

$1,123 / week

1 / 50

Vacation home accommodation

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from $401 / night

$2,806 / week

1 / 63

Vacation home in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $114 / night

$794 / week

1 / 37

Vacation villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $195 / night

$1,363 / week

1 / 25

Kissimmee City Vacation condo rental

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $178 / night

$945 / week

1 / 14

Vacation villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

from $252 / night

$1,764 / week

1 / 49

Vacation villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $110 / night

$762 / week

1 / 22

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from $407 / night

$2,846 / week

1 / 59

Vacation home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $92 / night

$550 - $1,031 / week

1 / 23

Vacation villa in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from $265 / night

$1,852 / week

1 / 48

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