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Kissimmee City Holidays & City Breaks - Holiday Lettings

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148 properties suitable for city breaks and holidays

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Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £114 / night

£796 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £108 / night

£899 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £152 / night

£921 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

from £341 / night

£2,158 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £90 / night

£630 / week

1 / 20

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £89 / night

£623 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £194 / night

£1,708 - £1,833 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday townhouse with golf nearby in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £128 / night

£894 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa in Clermont

Clermont villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £99 / night

£675 - £958 / week

1 / 40

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 £167 / night

£1,165 / week

1 / 29

Great rentals within 20 miles that match your search

Home rental in Davenport

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £116 / night

£810 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa in Reunion

Reunion villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £178 / night

£1,246 / week

1 / 60

Great rentals within 20 miles that match your search

Kissimmee holiday apartment rental

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £90 / night

£540 / week

1 / 13

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 15

from £230 / night

£1,605 / week

1 / 70

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

from £173 / night

£1,214 / week

1 / 30

Great rentals within 20 miles that match your search

Home rental in ChampionsGate

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £122 / night

£850 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday villa with shared pool, golf nearby in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £134 / night

£938 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

from £450 / night

£3,147 / week

1 / 117

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from £184 / night

£1,283 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £171 / night

£1,133 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from £314 / night

£2,197 / week

1 / 73

Great rentals within 20 miles that match your search

Celebration holiday townhouse rental

Celebration townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £89 / night

£623 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home letting

Celebration house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £130 / night

£899 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday home in Loughman

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £113 / night

£787 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday villa letting

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £315 / night

£2,203 / 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 £142 / night

£980 / week

1 / 9

Great rentals within 20 miles that match your search

Orlando holiday townhouse rental

Orlando townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £180 / night

£1,259 / week

1 / 36

Great rentals within 20 miles that match your search

Four Corners holiday apartment rental

Four Corners apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £244 / night

£1,709 / 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 £251 / night

£1,618 - £2,184 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £125 / night

£875 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday hotel apartment in Kissimmee

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £77 / night

£535 / week

1 / 27

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

from £207 / night

£1,448 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday townhouse rental

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £99 / night

£693 / week

1 / 35

Great rentals within 20 miles that match your search

Home accommodation in Reunion

Reunion house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

from £338 / night

£2,248 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £116 / night

£675 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday townhouse in Four Corners

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £67 / night

£452 - £1,563 / week

1 / 34

Great rentals within 20 miles that match your search

Kissimmee holiday hotel apartment rental

Kissimmee hotel apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £80 / night

£567 / week

1 / 36

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 £149 / night

£1,070 - £1,731 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday villa rental

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

from £264 / night

£1,844 / 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

from £98 / night

£686 / week

1 / 26

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