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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
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
  • Apartment (1)
  • Villa (20)
  • House (8)
  • Townhouse (1)
  • Condo (1)

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31 Holiday homes

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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

£960 / week

1 / 29

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

£2,016 / week

1 / 59

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £228 / night

£1,597 / week

1 / 37

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18
2 reviews

from £156 / night

£1,088 / week

1 / 29

Great rentals within 20 miles that match your search

Kissimmee holiday home accommodation

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £110 / night

£768 / week

1 / 18

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

£698 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
5 reviews

from £170 / night

£1,184 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday home rental

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
2 reviews

from £87 / night

£607 / week

1 / 49

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 £137 / night

£954 / week

1 / 48

Great rentals within 20 miles that match your search

Townhouse rental in Four Corners

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8
6 reviews

from £87 / night

£608 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
5 reviews

from £165 / night

£915 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £411 / night

£2,874 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday villa accommodation

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £640 / night

£4,480 / week

1 / 23

Great rentals within 20 miles that match your search

Villa rental in Kissimmee with swimming pool

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £212 / night

£1,479 / week

1 / 48

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
3 reviews

from £138 / night

£960 - £1,536 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday home accommodation

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 17
7 reviews

from £389 / night

£2,720 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home with shared pool in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8
7 reviews

from £260 / night

£1,820 - £2,294 / week

1 / 49

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 £105 / night

£1,004 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Four Corners

Four Corners villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £293 / night

£2,048 / week

1 / 25

Great rentals within 20 miles that match your search

Four Corners holiday villa rental

Four Corners villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £275 / night

£1,920 / week

1 / 21

Great rentals within 20 miles that match your search

Villa accommodation in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £138 / night

£960 - £1,536 / week

1 / 47

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 £320 / night

£2,067 - £3,072 / week

1 / 48

Great rentals within 20 miles that match your search

Four Corners holiday villa let

Four Corners villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 17
9 reviews

from £365 / night

£2,554 / week

1 / 65

Great rentals within 20 miles that match your search

Kissimmee holiday apartment let

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £100 / night

£598 / week

1 / 30

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16
4 reviews

from £320 / night

£2,240 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday villa in Four Corners

Four Corners villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12
1 review

from £275 / night

£1,367 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday condo rental

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
14 reviews

from £98 / night

£516 - £1,031 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
13 reviews

from £149 / night

£1,042 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16
2 reviews

from £320 / night

£2,240 / week

1 / 59

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
8 reviews

from £110 / night

£750 - £823 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday villa rental

Four Corners villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from £146 / night

£1,022 / week

1 / 26

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Holiday villa rental

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Horse riding

from £144 / night

£1,006 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Horse riding

from £262 / night

£1,829 / week

1 / 7

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: Horse riding

from £392 / night

£2,743 / 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: Tennis in town

4 reviews

from £138 / night

£916 - £1,031 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Horse riding

from £115 / night

£800 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home with indoor pool in Emerald Island

Emerald Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Horse riding

24 reviews

from £138 / night

£960 - £1,152 / week

1 / 100

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 9 bathrooms
  • sleeps 8

1 filter does not match: Horse riding

31 reviews

from £182 / night

£1,274 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday home in Kissimmee

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Horse riding

2 reviews

from £229 / night

£1,600 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Horse riding

22 reviews

from £96 / night

£672 / week

1 / 30

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