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50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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11,961 Vacation rentals

Vacation condo with golf nearby in Kissimmee

Kissimmee condo

3 bedrooms • 2 bathrooms • sleeps 6

67 reviews

from $88 / night

$368 - $588 / week

1 / 27

Kissimmee Vacation home rental

Kissimmee house

4 bedrooms • 3 bathrooms • sleeps 10

13 reviews

from $210 / night

$1,470 / week

1 / 100

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

29 reviews

from $120 / night

$900 - $1,248 / week

1 / 24

Vacation villa with swimming pool in Kissimmee

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

38 reviews

from $307 / night

$887 - $1,048 / week

1 / 21

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

28 reviews

from $178 / night

$1,214 - $1,295 / week

1 / 30

Vacation villa with swimming pool in Bellavida Resort

Kissimmee villa

4 bedrooms • 4 bathrooms • sleeps 8

43 reviews

from $192 / night

$1,039 - $1,359 / week

1 / 22

Vacation home rental

Kissimmee house

5 bedrooms • 4 bathrooms • sleeps 13

18 reviews

from $159 / night

$1,068 - $1,496 / week

1 / 38

Vacation villa in Kissimmee

Kissimmee villa

5 bedrooms • 5 bathrooms • sleeps 10

1 review

from $404 / night

$2,829 / week

1 / 28

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

21 reviews

from $236 / night

$1,292 / week

1 / 18

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 9

21 reviews

from $168 / night

$1,170 - $1,372 / week

1 / 30

Vacation villa in Seasons Resort

Kissimmee villa

5 bedrooms • 4 bathrooms • sleeps 10

42 reviews

from $112 / night

$640 - $1,119 / week

1 / 17

Vacation villa in Kissimmee

Kissimmee villa

4 bedrooms • 2 bathrooms • sleeps 6

13 reviews

from $126 / night

$911 / week

1 / 19

Vacation villa in Westside

Kissimmee villa

4 bedrooms • 4 bathrooms • sleeps 9

53 reviews

from $155 / night

$1,071 - $1,380 / week

1 / 91

Vacation townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms • 3 bathrooms • sleeps 8

21 reviews

from $162 / night

$973 / week

1 / 90

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

41 reviews

from $173 / night

$1,179 - $1,612 / week

1 / 56

Vacation home rental

Kissimmee house

4 bedrooms • 3 bathrooms • sleeps 8

23 reviews

from $122 / night

$850 / week

1 / 46

Kissimmee Vacation villa rental

Kissimmee villa

4 bedrooms • 2 bathrooms • sleeps 8

8 reviews

from $218 / night

$1,523 - $1,844 / week

1 / 34

Kissimmee Vacation villa rental

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

9 reviews

from $195 / night

$1,093 - $1,538 / week

1 / 23

Vacation villa rental

Kissimmee villa

4 bedrooms • 2 bathrooms • sleeps 8

9 reviews

from $152 / night

$1,063 / week

1 / 45

Vacation villa in Kissimmee City

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

36 reviews

from $85 / night

$530 - $1,060 / week

1 / 36

Kissimmee Vacation townhouse rental

Kissimmee townhouse

3 bedrooms • 3 bathrooms • sleeps 6

4 reviews

from $114 / night

$713 / week

1 / 16

Kissimmee Vacation villa rental

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

41 reviews

from $146 / night

$931 - $1,020 / week

1 / 18

Kissimmee Vacation villa accommodation

Kissimmee villa

4 bedrooms • 2 bathrooms • sleeps 8

13 reviews

from $144 / night

$1,002 - $1,243 / week

1 / 45

Bungalow rental in Kissimmee

Kissimmee bungalow

4 bedrooms • 2 bathrooms • sleeps 8

25 reviews

from $155 / night

$1,019 / week

1 / 49

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

Kissimmee villa

2 bedrooms • 2 bathrooms • sleeps 8

3 reviews

from $274 / night

$1,918 / week

1 / 18

Villa rental in Kissimmee with golf nearby

Kissimmee villa

6 bedrooms • 4 bathrooms • sleeps 14

13 reviews

from $233 / night

$1,527 - $2,415 / week

1 / 52

Emerald Isle Kissimmee Vacation villa rental

Kissimmee villa

5 bedrooms • 4 bathrooms • sleeps 12

37 reviews

from $210 / night

$1,394 - $1,733 / week

1 / 54

Vacation villa in Doral Woods

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

31 reviews

from $159 / night

$1,111 - $1,526 / week

1 / 24

Vacation villa in Kissimmee

Kissimmee villa

4 bedrooms • 4 bathrooms • sleeps 8

58 reviews

from $229 / night

$1,603 - $1,775 / week

1 / 28

Villa accommodation in Kissimmee

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

6 reviews

from $112 / night

$783 / week

1 / 26

Villa rental in Kissimmee with swimming pool

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

72 reviews

from $211 / night

$1,004 - $1,037 / week

1 / 45

Kissimmee Vacation villa rental

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

38 reviews

from $128 / night

$799 - $1,007 / week

1 / 30

Doral Woods Vacation villa rental

Kissimmee villa

4 bedrooms • 2 bathrooms • sleeps 8

33 reviews

from $157 / night

$1,039 / week

1 / 27

Vacation villa rental

Kissimmee villa

4 bedrooms • 3 bathrooms • sleeps 8

46 reviews

from $162 / night

$1,131 / week

1 / 37

Vacation villa in Kissimmee

Kissimmee villa

5 bedrooms • 4 bathrooms • sleeps 12

24 reviews

from $178 / night

$1,243 - $1,443 / week

1 / 28

Vacation villa rental

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

16 reviews

from $146 / night

$970 / week

1 / 36

Kissimmee Vacation villa rental

Kissimmee villa

5 bedrooms • 3 bathrooms • sleeps 10

29 reviews

from $160 / night

$1,119 - $1,263 / week

1 / 43

Vacation townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms • 3 bathrooms • sleeps 10

10 reviews

from $184 / night

$1,197 - $1,518 / week

1 / 20

Vacation townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms • 3 bathrooms • sleeps 10

10 reviews

from $144 / night

$945 / week

1 / 20

Villa rental in Kissimmee

Kissimmee villa

3 bedrooms • 2 bathrooms • sleeps 6

5 reviews

from $154 / night

$1,073 / week

1 / 16

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