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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

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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 (12)
  • Villa (83)
  • House (30)
  • Bungalow (1)
  • Townhouse (13)
  • Condo (5)
  • Hotel apartment (1)

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145 Holiday homes

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Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
91 reviews

from £161 / night

£859 - £974 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
31 reviews

from £110 / night

£770 / week

1 / 21

Great rentals within 20 miles that match your search

Bungalow rental in Kissimmee

Kissimmee bungalow

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8
26 reviews

from £142 / night

£908 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday townhouse with shared pool in Davenport

Davenport townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6
20 reviews

from £69 / night

£458 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £320 / night

£2,236 / week

1 / 13

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
12 reviews

from £139 / night

£970 - £1,131 / week

1 / 62

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12
56 reviews

from £207 / night

£1,025 - £1,260 / week

1 / 22

Great rentals within 20 miles that match your search

Villa rental in Four Corners with swimming pool

Four Corners villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8
92 reviews

from £142 / night

£832 / week

1 / 55

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14
2 reviews

from £151 / night

£1,056 / week

1 / 22

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10
4 reviews

from £202 / night

£1,408 / week

1 / 36

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

Kissimmee holiday villa rental

Kissimmee villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £138 / night

£1,152 - £2,560 / week

1 / 94

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £280 / night

£1,959 / week

1 / 35

Great rentals within 20 miles that match your search

Home letting in Four Corners

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £91 / night

£633 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday apartment in Davenport

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £183 / night

£1,280 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home letting

Celebration house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £132 / night

£913 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £229 / night

£1,597 / week

1 / 34

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £110 / night

£767 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Four Corners

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
12 reviews

from £100 / night

£698 / week

1 / 39

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
44 reviews

from £164 / night

£1,143 - £1,509 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday villa with indoor pool in Reunion

Reunion villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 19

from £228 / night

£2,190 - £4,202 / 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 £91 / night

£595 - £869 / week

1 / 34

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

£824 / week

1 / 58

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

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 rental

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14
13 reviews

from £165 / night

£1,098 - £2,377 / week

1 / 14

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

Condo rental in Four Corners with shared pool

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £137 / night

£958 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Four Corners

Four Corners villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £183 / night

£1,280 / week

1 / 81

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

from £320 / night

£2,236 / week

1 / 72

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 / 67

Great rentals within 20 miles that match your search

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22
11 reviews

from £480 / night

£3,360 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from £124 / night

£863 / week

1 / 42

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £183 / night

£1,277 / week

1 / 2

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

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

from £212 / night

£1,479 / week

1 / 51

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