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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Villas and Condos in Kissimmee City

Holiday Rentals in Kissimmee City - Holiday Lettings - Villas

Price per night

£1 £750 -

Bedrooms

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Apartment (11)
  • Villa (67)
  • House (22)
  • Townhouse (35)
  • Condo (35)

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170 Holiday homes

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Sauna
Tennis in town

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £91 / night

£634 / week

1 / 13

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14
4 reviews

from £453 / night

£2,652 / week

1 / 37

Great rentals within 20 miles that match your search

Home rental in Reunion with shared pool, golf nearby

Reunion house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 22

from £343 / night

£640 - £3,840 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £213 / night

£1,491 / week

1 / 67

Great rentals within 20 miles that match your search

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £138 / night

£960 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

from £426 / night

£2,976 / week

1 / 92

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

from £426 / night

£2,976 / week

1 / 92

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £213 / night

£1,491 / week

1 / 67

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £374 / night

£2,618 / week

1 / 48

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £181 / night

£1,267 / week

1 / 68

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £181 / night

£1,267 / week

1 / 69

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £385 / night

£2,695 / week

1 / 59

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

from £385 / night

£2,695 / week

1 / 61

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £192 / night

£1,344 / week

1 / 36

Great rentals within 20 miles that match your search

Home rental in Four Corners

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

from £243 / night

£1,646 / week

1 / 56

Great rentals within 20 miles that match your search

Celebration holiday condo rental

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £60 / night

£416 / week

1 / 11

Great rentals within 20 miles that match your search

Celebration holiday condo rental

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £69 / night

£480 / week

1 / 11

Great rentals within 20 miles that match your search

Celebration holiday condo rental

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £60 / night

£416 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £392 / night

£2,739 / week

1 / 81

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from £289 / night

£2,023 / week

1 / 55

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £374 / night

£2,618 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £181 / night

£1,267 / week

1 / 71

Great rentals within 20 miles that match your search

Holiday townhouse rental

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £181 / night

£1,267 / week

1 / 71

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £159 / night

£1,108 / week

1 / 46

Great rentals within 20 miles that match your search

Holiday townhouse with shared pool in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £165 / night

£1,152 / week

1 / 46

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £392 / night

£2,739 / week

1 / 82

Great rentals within 20 miles that match your search

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £170 / night

£1,191 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in ChampionsGate

ChampionsGate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

from £298 / night

£2,080 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £159 / night

£1,108 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £267 / night

£1,869 / week

1 / 70

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £203 / night

£1,421 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from £289 / night

£2,023 / week

1 / 43

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 18

from £392 / night

£2,739 / week

1 / 57

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £92 / night

£640 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday townhouse with swimming pool in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £170 / night

£1,191 / week

1 / 52

Great rentals within 20 miles that match your search

Home rental in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £80 / night

£557 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday villa letting

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £320 / night

£2,240 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £229 / night

£1,600 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday condo letting

Four Corners condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from £75 / night

£525 / week

1 / 55

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £267 / night

£1,869 / week

1 / 70

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