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Viewing 40 of 494 rentals in Kissimmee City

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

Holiday Rentals in Kissimmee City - Holiday Lettings - Villas

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
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  • 4 and above
  • 3 and above
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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 (3)
  • Villa (41)
  • House (18)
  • Townhouse (6)
  • Condo (5)
  • Hotel apartment (2)

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75 Holiday homes

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Water sports

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

from £347 / night

£2,195 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Orlando

Orlando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £170 / night

£1,184 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from £319 / night

£2,230 / week

1 / 73

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

Kissimmee holiday condo rental

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £144 / night

£997 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £255 / night

£1,645 - £2,221 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday townhouse rental

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £101 / night

£704 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £91 / night

£595 - £869 / week

1 / 34

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 - £1,519 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Orlando

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

from £151 / night

£1,088 - £1,728 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday villa rental

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

from £268 / night

£1,876 / week

1 / 62

Great rentals within 20 miles that match your search

Holiday hotel apartment with golf nearby in Kissimmee

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
22 reviews

from £100 / night

£698 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Orlando

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16
2 reviews

from £170 / night

£1,459 - £2,912 / week

1 / 44

Great rentals within 20 miles that match your search

Villa letting in ChampionsGate with golf nearby

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from £268 / night

£1,876 / week

1 / 66

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from £275 / night

£1,920 / week

1 / 68

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 24

from £388 / night

£2,714 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

from £211 / night

£1,475 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 24

from £388 / night

£2,715 / week

1 / 80

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 £320 / night

£2,240 / week

1 / 65

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 £325 / night

£2,272 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday home with shared pool in Four Corners

Four Corners house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £110 / night

£767 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £92 / night

£639 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

from £212 / night

£1,479 / week

1 / 51

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

from £212 / night

£1,479 / week

1 / 48

Great rentals within 20 miles that match your search

Apartment rental in Kissimmee with shared pool

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from £86 / night

£573 - £1,031 / week

1 / 39

Great rentals within 20 miles that match your search

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £93 / night

£652 / week

1 / 50

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from £206 / night

£1,438 / week

1 / 33

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

from £320 / night

£2,236 / week

1 / 62

Great rentals within 20 miles that match your search

Holiday hotel apartment with golf nearby in Orlando

Orlando hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £245 / night

£1,716 / week

1 / 25

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £212 / night

£1,479 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in ChampionsGate

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from £320 / night

£2,236 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Reunion

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

from £639 / night

£4,472 / week

1 / 58

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7
38 reviews

from £96 / night

£636 / week

1 / 24

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18
1 review

from £211 / night

£1,475 / week

1 / 49

Great rentals within 20 miles that match your search

ChampionsGate holiday villa rental

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

from £268 / night

£1,876 / week

1 / 62

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
39 reviews

from £172 / night

£802 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Orlando

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £105 / night

£703 - £1,150 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £264 / night

£1,844 / week

1 / 56

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with golf nearby

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £216 / night

£1,508 / week

1 / 78

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 £320 / night

£2,240 / week

1 / 65

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