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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Houses and Villas in Oak Island Harbor

Holiday Rentals in Oak Island Harbor - Holiday Lettings - Villas

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 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 (19)
  • Villa (46)
  • House (70)
  • Townhouse (17)
  • Condo (30)
  • Hotel apartment (2)

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184 Holiday homes

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Tennis in town
Under 5s

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
95 reviews

from £138 / night

£962 / week

1 / 29

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

£523 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday home with shared pool in Four Corners

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13
1 review

from £165 / night

£1,152 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday villa letting

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
26 reviews

from £132 / night

£922 / week

1 / 37

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

£642 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £289 / night

£2,020 / week

1 / 59

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12
2 reviews

from £197 / night

£1,740 - £1,868 / week

1 / 33

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14
4 reviews

from £454 / night

£2,657 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday apartment rental

Four Corners apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £106 / night

£738 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £229 / night

£1,603 / week

1 / 37

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £138 / night

£916 / week

1 / 4

Great rentals within 20 miles that match your search

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £138 / night

£962 / week

1 / 43

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

from £183 / night

£1,145 - £1,832 / week

1 / 36

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £197 / night

£1,379 / week

1 / 45

Great rentals within 20 miles that match your search

Home rental in Four Corners

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

from £243 / night

£1,649 / week

1 / 56

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
3 reviews

from £176 / night

£1,238 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 24

from £556 / night

£3,892 / week

1 / 69

Great rentals within 20 miles that match your search

Home rental in Four Corners

Four Corners house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £131 / night

£915 / week

1 / 42

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £153 / night

£1,066 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £330 / night

£2,309 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

from £390 / night

£2,725 / week

1 / 47

Great rentals within 20 miles that match your search

Home rental in Four Corners

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £202 / night

£1,228 / week

1 / 22

Great rentals within 20 miles that match your search

Condo rental in Four Corners

Four Corners condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £92 / night

£642 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Four Corners

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £265 / night

£1,856 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £105 / night

£731 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £229 / night

£1,603 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £229 / night

£1,603 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

from £220 / night

£1,539 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £82 / night

£571 / week

1 / 29

Great rentals within 20 miles that match your search

Four Corners holiday apartment rental

Four Corners apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £249 / night

£1,741 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday condo in Four Corners

Four Corners condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £103 / night

£718 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £165 / night

£1,155 / week

1 / 26

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £110 / night

£770 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8
9 reviews

from £128 / night

£892 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday townhouse in Reunion

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £137 / night

£915 / week

1 / 41

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

£699 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

from £101 / night

£706 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £92 / night

£642 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £87 / night

£610 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

from £101 / night

£706 / week

1 / 29

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