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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Villas and Houses 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 (4)
  • Villa (17)
  • House (9)
  • Townhouse (2)

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32 Holiday homes

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Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from £462 / night

£3,194 - £4,165 / week

1 / 53

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Four Corners

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £129 / night

£901 / week

1 / 16

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £185 / night

£1,290 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £227 / night

£1,588 / week

1 / 20

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £101 / night

£707 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

from £185 / night

£1,157 - £1,852 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
23 reviews

from £176 / night

£1,167 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday home in Celebration

Celebration house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 13

from £269 / night

£1,879 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

from £162 / night

£1,132 / week

1 / 28

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
44 reviews

from £166 / night

£1,157 - £1,528 / week

1 / 43

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 £138 / night

£966 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday villa letting

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20
33 reviews

from £231 / night

£1,545 / week

1 / 105

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £176 / night

£1,180 - £1,620 / week

1 / 19

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
6 reviews

from £158 / night

£1,102 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £93 / night

£648 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Four Corners

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £324 / night

£2,268 / week

1 / 45

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14
8 reviews

from £324 / night

£2,268 / week

1 / 72

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Four Corners

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12
10 reviews

from £107 / night

£1,019 / week

1 / 36

Great rentals within 20 miles that match your search

Apartment accommodation in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
91 reviews

from £102 / night

£713 / week

1 / 25

Great rentals within 20 miles that match your search

Apartment rental in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
13 reviews

from £93 / night

£648 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
1 review

from £269 / night

£1,879 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Four Corners

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12
72 reviews

from £324 / night

£2,092 - £3,110 / week

1 / 48

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £129 / night

£901 / week

1 / 42

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16
4 reviews

from £324 / night

£2,268 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12
1 review

from £148 / night

£972 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8
33 reviews

from £93 / night

£648 / week

1 / 18

Great rentals within 20 miles that match your search

Kissimmee holiday townhouse rental

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7
23 reviews

from £162 / night

£1,134 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
2 reviews

from £199 / night

£1,393 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16
2 reviews

from £324 / night

£2,268 / week

1 / 59

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14
3 reviews

from £324 / night

£2,268 / week

1 / 68

Great rentals within 20 miles that match your search

Kissimmee holiday villa let

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
44 reviews

from £115 / night

£722 - £922 / week

1 / 30

Great rentals within 20 miles that match your search

Four Corners holiday home rental

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £204 / night

£1,426 / week

1 / 15

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Home rental in Kissimmee with swimming pool

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22

1 filter does not match: Cot available

11 reviews

from £486 / night

£3,402 / week

1 / 33

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: Cot available

5 reviews

from £172 / night

£1,199 / week

1 / 48

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: Cot available

from £185 / night

£972 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Cot available

from £146 / night

£1,019 / week

1 / 9

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: Cot available

from £273 / night

£1,912 / 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: Cot available

2 reviews

from £212 / night

£1,484 / week

1 / 21

Great rentals within 20 miles that match your search

Condo rental in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Cot available

from £397 / night

£2,777 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Cot available

4 reviews

from £138 / night

£916 - £1,031 / week

1 / 18

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