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Viewing 40 of 4,042 rentals in Kissimmee City

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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Houses and Villas 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 (2)
  • Villa (3)
  • House (3)
  • Townhouse (2)
  • Studio (1)
  • Condo (1)

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12 Holiday homes

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Pets allowed

Great rentals within 20 miles that match your search

Davenport holiday studio rental

Davenport studio

  • Studio
  • 2 bathrooms
  • sleeps 8

from £138 / night

£864 - £1,440 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home with shared pool in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £115 / night

£800 - £1,297 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £92 / night

£549 - £1,097 / week

1 / 25

Great rentals within 20 miles that match your search

Townhouse letting in Davenport

Davenport townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £115 / night

£686 - £823 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Davenport

Davenport apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10
2 reviews

from £94 / night

£653 / week

1 / 20

Great rentals within 20 miles that match your search

Townhouse rental in Kissimmee with shared pool

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £69 / night

£412 - £768 / week

1 / 19

Great rentals within 20 miles that match your search

Home rental in Davenport

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £119 / night

£825 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home rental

Davenport house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15
38 reviews

from £274 / night

£1,918 - £2,142 / week

1 / 63

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £183 / night

£1,276 / week

1 / 5

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7
38 reviews

from £97 / night

£637 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £144 / night

£1,008 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
90 reviews

from £101 / night

£710 - £762 / week

1 / 28

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Orlando holiday villa rental

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

4 reviews

from £229 / night

£1,603 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

2 reviews

from £147 / night

£916 - £1,466 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday apartment in Davenport

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £161 / night

£1,122 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

5 reviews

from £170 / night

£1,187 / week

1 / 48

Great rentals within 20 miles that match your search

Orlando holiday apartment accommodation

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £266 / night

£1,860 / week

1 / 8

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

15 reviews

from £138 / night

£962 / week

1 / 19

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £183 / night

£1,282 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

2 reviews

from £184 / night

£871 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £157 / night

£1,100 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

1 review

from £106 / night

£738 / week

1 / 22

Great rentals within 20 miles that match your search

Home rental in Orlando with swimming pool, golf nearby

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

1 filter does not match: Pets allowed

2 reviews

from £145 / night

£1,026 - £1,732 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday hotel apartment in Orlando

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £243 / night

£1,700 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo in Reunion

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £109 / night

£763 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

1 review

from £115 / night

£802 / week

1 / 41

Great rentals within 20 miles that match your search

Condo rental in Four Corners with golf nearby

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Pets allowed

1 review

from £73 / night

£824 / week

1 / 27

Great rentals within 20 miles that match your search

Villa rental in Orlando with shared pool

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £137 / night

£956 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £106 / night

£738 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday condo with indoor pool in Clermont

Clermont condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

27 reviews

from £110 / night

£642 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

20 reviews

from £152 / night

£1,058 / week

1 / 48

Great rentals within 20 miles that match your search

Townhouse accommodation in Reunion with golf nearby

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

3 reviews

from £129 / night

£808 - £895 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £367 / night

£2,565 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Orlando

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £183 / night

£962 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £275 / night

£1,924 / week

1 / 18

Great rentals within 20 miles that match your search

Kissimmee holiday apartment rental

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

1 review

from £92 / night

£642 / week

1 / 4

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

1 filter does not match: Pets allowed

8 reviews

from £550 / night

£3,664 - £3,921 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday townhouse with shared pool in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £271 / night

£1,892 / week

1 / 18

Great rentals within 20 miles that match your search

Orlando holiday home rental

Orlando house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Pets allowed

2 reviews

from £210 / night

£1,469 / week

1 / 21

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

2 reviews

from £97 / night

£642 / week

1 / 81

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