Updating

Dates
...

Viewing 40 of 197 rentals in Oak Island Harbor

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
> 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 (6)
  • Villa (18)
  • House (8)
  • Townhouse (5)
  • Condo (1)

All filters (2)

Filters (2)

Clear filters

38 Holiday homes

Why am I receiving these results?

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

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10
63 reviews

from £123 / night

£859 / week

1 / 24

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

£1,733 - £1,861 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday townhouse in Four Corners

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £110 / night

£831 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £229 / night

£1,597 / week

1 / 37

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

£1,232 / week

1 / 30

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

£1,086 / week

1 / 29

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 £160 / night

£1,116 / 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 £136 / night

£912 / 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

£697 / week

1 / 39

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

Four Corners holiday condo rental

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
34 reviews

from £80 / night

£479 / week

1 / 13

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 £136 / night

£952 / 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

£607 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa letting

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20
33 reviews

from £228 / night

£1,523 / week

1 / 105

Great rentals within 20 miles that match your search

Apartment rental in Kissimmee with shared pool

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £105 / night

£735 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday townhouse in Four Corners

Four Corners townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10
21 reviews

from £114 / night

£799 - £895 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £92 / night

£639 / week

1 / 26

Great rentals within 20 miles that match your search

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22
11 reviews

from £479 / night

£3,354 / week

1 / 33

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

£913 / week

1 / 39

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 £211 / night

£1,476 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday home accommodation

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 17
7 reviews

from £388 / night

£2,715 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday villa rental

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15
17 reviews

from £238 / night

£1,661 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home in Four Corners

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £109 / night

£761 / week

1 / 64

Great rentals within 20 miles that match your search

Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

from £458 / night

£3,206 / week

1 / 29

Great rentals within 20 miles that match your search

Villa rental in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14
8 reviews

from £320 / night

£2,236 / 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 £105 / night

£1,004 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday apartment accommodation

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
8 reviews

from £92 / night

£639 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday townhouse in Celebration

Celebration townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9
1 review

from £215 / night

£1,369 / week

1 / 46

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

£2,063 - £3,067 / week

1 / 48

Great rentals within 20 miles that match your search

Kissimmee holiday home rental

Kissimmee house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 17
22 reviews

from £365 / night

£2,556 / week

1 / 36

Great rentals within 20 miles that match your search

Kissimmee holiday apartment let

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £100 / night

£597 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
22 reviews

from £96 / night

£671 / 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

£2,236 / 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 £274 / night

£1,365 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8
33 reviews

from £92 / night

£639 / week

1 / 18

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

£2,236 / week

1 / 59

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.

Clear all filters

Holiday villa in Kissimmee

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Walking holidays

8 reviews

from £110 / night

£749 - £822 / week

1 / 11

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: Walking holidays

4 reviews

from £138 / night

£916 - £1,031 / week

1 / 18

×

Also consider