Updating

Dates
...

Viewing 40 of 3,458 rentals in Kissimmee City

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

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)
  • 5
  • 4 and above
  • 3 and above
Tripadvisor rating Vrbo rating
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
  • Condo (611)
  • Apartment (151)
  • Villa (822)
  • Cottage (1)
  • House (1,407)
  • Penthouse (1)
  • Bungalow (1)
  • Townhouse (331)
  • Studio (2)
  • Hotel apartment (20)

All filters (1)

Filters (2)

Clear filters

611 Holiday homes

Why am I receiving these results?
Applied filters (2)
Condo
Washing machine

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5
7 reviews

from £108 / night

£521 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo in Davenport

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
2 reviews

from £137 / night

£959 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday condo in Celebration

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £81 / night

£1,596 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £126 / night

£882 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Reunion

Reunion condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £119 / night

£712 - £1,095 / week

1 / 28

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from £100 / night

£638 / week

1 / 30

Great rentals within 20 miles that match your search

Celebration holiday condo let

Celebration condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £110 / night

£657 - £849 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
3 reviews

from £92 / night

£639 / week

1 / 20

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £92 / night

£639 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £81 / night

£563 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday condo letting

Celebration condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7
1 review

from £83 / night

£493 - £822 / week

1 / 15

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £91 / night

£633 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday condo in ChampionsGate

ChampionsGate condo

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 30

from £237 / night

£1,655 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
3 reviews

from £72 / night

£505 / week

1 / 33

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £96 / night

£671 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday condo in Davenport

Davenport condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £73 / night

£511 / week

1 / 48

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from £133 / night

£927 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £79 / night

£522 - £2,183 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £81 / night

£563 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £125 / night

£876 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

from £174 / night

£1,214 / week

1 / 62

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £88 / night

£614 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday condo letting

Lake Buena Vista condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £216 / night

£1,430 - £1,730 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £448 / night

£2,926 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo letting

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £116 / night

£812 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £116 / night

£812 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £68 / night

£473 / week

1 / 34

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £73 / night

£511 / week

1 / 27

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £183 / night

£1,278 / week

1 / 67

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £95 / night

£665 / week

1 / 48

Great rentals within 20 miles that match your search

Celebration holiday condo rental

Celebration condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

from £89 / night

£589 - £2,913 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Loughman

Loughman condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £92 / night

£639 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £71 / night

£492 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday condo accommodation

Kissimmee condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £120 / night

£837 / week

1 / 23

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

£1,308 - £1,560 / week

1 / 17

Great rentals within 20 miles that match your search

Reunion holiday condo rental

Reunion condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £78 / night

£511 - £1,112 / week

1 / 42

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £84 / night

£588 / week

1 / 49

Great rentals within 20 miles that match your search

Kissimmee holiday condo rental

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £78 / night

£543 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £84 / night

£588 / week

1 / 46

Great rentals within 20 miles that match your search

Condo rental in Kissimmee with shared pool

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £78 / night

£543 / week

1 / 45

×

Also consider