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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 -

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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 (5)
  • Villa (44)
  • House (24)
  • Townhouse (18)
  • Condo (27)
  • Hotel apartment (2)

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120 Holiday homes

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Heated pool
Sauna

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 £454 / night

£2,657 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £164 / night

£1,056 / week

1 / 34

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 condo letting

Lake Buena Vista condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £216 / night

£1,433 - £1,733 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday condo rental

Lake Buena Vista condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £191 / night

£1,294 - £1,538 / week

1 / 17

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 condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £369 / night

£2,279 - £7,418 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £400 / night

£2,353 - £7,418 / week

1 / 44

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £159 / night

£1,110 / week

1 / 46

Great rentals within 20 miles that match your search

Holiday home with shared pool in Davenport

Davenport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £87 / night

£504 / week

1 / 13

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 condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £351 / night

£2,183 - £7,418 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £357 / night

£2,205 - £7,418 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £229 / night

£1,603 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday home rental

Davenport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £69 / night

£481 / week

1 / 12

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

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £110 / night

£768 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £138 / night

£960 / week

1 / 23

Great rentals within 20 miles that match your search

Four Corners holiday condo rental

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £328 / night

£1,942 - £7,418 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £339 / night

£2,038 - £7,418 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £330 / night

£2,028 - £7,168 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £329 / night

£1,964 - £7,418 / week

1 / 43

Great rentals within 20 miles that match your search

Davenport holiday home rental

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £109 / night

£759 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday townhouse with golf nearby in Davenport

Davenport townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9
33 reviews

from £173 / night

£1,210 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £157 / night

£1,097 / week

1 / 16

Great rentals within 20 miles that match your search

Townhouse rental in Davenport

Davenport townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £133 / night

£928 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday townhouse in Four Corners

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £68 / night

£459 - £1,442 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday home with swimming pool, golf nearby in ChampionsGate

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £78 / night

£544 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday villa rental

Orlando villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
33 reviews

from £118 / night

£826 / week

1 / 58

Great rentals within 20 miles that match your search

Townhouse rental in Four Corners

Four Corners townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £135 / night

£943 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7
2 reviews

from £100 / night

£698 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday townhouse with golf nearby in Davenport

Davenport townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £119 / night

£828 / week

1 / 14

Great rentals within 20 miles that match your search

Villa rental in Four Corners with swimming pool, golf nearby

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
2 reviews

from £137 / night

£954 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £325 / night

£2,272 / week

1 / 59

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

from £321 / night

£2,245 / week

1 / 65

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £326 / night

£2,277 / week

1 / 58

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with golf nearby

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £326 / night

£2,277 / week

1 / 57

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £326 / night

£2,277 / week

1 / 58

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