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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 (15)
  • Villa (77)
  • House (38)
  • Townhouse (40)
  • Studio (1)
  • Condo (47)
  • Hotel apartment (2)

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220 Holiday homes

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Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £81 / night

£1,599 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday home with shared pool in Davenport

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
6 reviews

from £115 / night

£800 / week

1 / 64

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 in Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
3 reviews

from £73 / night

£506 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £87 / night

£576 - £1,524 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday condo letting

Lake Buena Vista condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £222 / night

£1,437 - £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 £203 / night

£1,311 - £1,563 / week

1 / 17

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

£1,492 / 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 home in Kissimmee

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16
1 review

from £138 / night

£1,056 - £2,477 / week

1 / 46

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Four Corners

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £88 / night

£576 - £1,568 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
1 review

from £69 / night

£481 - £874 / week

1 / 35

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

£1,492 / week

1 / 67

Great rentals within 20 miles that match your search

Kissimmee holiday apartment rental

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £106 / night

£735 - £962 / week

1 / 34

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

£1,268 / 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

£1,268 / 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

Studio rental in Kissimmee

Kissimmee studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £97 / night

£677 - £905 / week

1 / 30

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

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £392 / night

£2,740 / week

1 / 81

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

£1,268 / 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

£1,268 / week

1 / 71

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £365 / night

£2,279 - £7,419 / 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 £394 / night

£2,353 - £7,419 / 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

£1,108 / 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

Holiday home with swimming pool in Four Corners

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £124 / night

£864 / week

1 / 44

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

£2,740 / 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 home in ChampionsGate

ChampionsGate house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £109 / night

£762 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £90 / night

£629 - £1,021 / week

1 / 35

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12
5 reviews

from £87 / night

£576 - £1,652 / week

1 / 62

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