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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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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 (19)
  • Villa (194)
  • House (88)
  • Penthouse (1)
  • Townhouse (23)
  • Condo (33)
  • Hotel apartment (1)

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359 Holiday homes

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Heated pool
Fishing

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Davenport

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
48 reviews

from £121 / night

£842 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
95 reviews

from £137 / night

£959 / week

1 / 29

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 shared pool, golf nearby in Davenport

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10
7 reviews

from £137 / night

£959 / week

1 / 33

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

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 28

from £273 / night

£1,910 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
26 reviews

from £152 / night

£921 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
52 reviews

from £138 / night

£965 / week

1 / 41

Great rentals within 20 miles that match your search

Clermont holiday villa rental

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £174 / night

£1,214 / week

1 / 18

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £293 / night

£2,051 / week

1 / 82

Great rentals within 20 miles that match your search

Holiday villa in Orlando

Orlando villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8
44 reviews

from £119 / night

£831 - £1,002 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home rental

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
3 reviews

from £228 / night

£1,591 / week

1 / 91

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
80 reviews

from £132 / night

£922 - £962 / week

1 / 73

Great rentals within 20 miles that match your search

Holiday home rental

Davenport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £156 / night

£1,086 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £229 / night

£1,597 / week

1 / 67

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £227 / night

£1,585 / week

1 / 39

Great rentals within 20 miles that match your search

Villa rental in Davenport with golf nearby

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £105 / night

£735 / week

1 / 32

Great rentals within 20 miles that match your search

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
15 reviews

from £138 / night

£962 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £153 / night

£1,067 / week

1 / 36

Great rentals within 20 miles that match your search

Villa rental in Davenport

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
1 review

from £126 / night

£882 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £288 / night

£2,013 / week

1 / 59

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, golf nearby

Four Corners villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £201 / night

£1,403 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
3 reviews

from £132 / night

£920 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 21

from £320 / night

£2,236 / week

1 / 26

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16
1 review

from £320 / night

£2,236 / week

1 / 57

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

from £440 / night

£3,079 / week

1 / 112

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

£831 / week

1 / 55

Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £138 / night

£916 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

from £440 / night

£3,079 / week

1 / 83

Great rentals within 20 miles that match your search

Holiday home with swimming pool, golf nearby in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 30

from £273 / night

£1,910 / week

1 / 87

Great rentals within 20 miles that match your search

Reunion holiday villa rental

Reunion villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
8 reviews

from £298 / night

£1,947 / week

1 / 43

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

£1,054 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

from £440 / night

£3,079 / week

1 / 106

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

from £440 / night

£3,079 / week

1 / 106

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 £130 / night

£907 / week

1 / 20

Great rentals within 20 miles that match your search

Duette holiday villa rental

Duette villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

from £161 / night

£1,123 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

from £440 / night

£3,079 / week

1 / 83

Great rentals within 20 miles that match your search

Holiday villa accommodation

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £293 / night

£2,048 / week

1 / 87

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £293 / night

£2,051 / week

1 / 72

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