Villas in Oak Island Harbor: Rent luxury villas in Oak Island Harbor

View larger map

Price per night

£103 Average

Price per night

to

Bedrooms

Bathrooms

Location

  • United States
  • Florida
  • Central Florida
  • Kissimmee

Location

  • All locations

More

Less

Property type

More

Less

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

50 Holiday homes

Filters applied: Horse riding (1)

1 / 24

Villa rental in Oak Island Harbor with golf nearby

Kissimmee / Oak Island Harbor

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £103 / night

£720 - £994 / week

Book

from £103 / night

More results near

Distance approx 0.03 miles from Oak Island Harbor Show on Map

(1) Excellent 

1 / 21

Holiday villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

Villa / 4 bedrooms / sleeps 9 / Min stay varies

Add to shortlist

from £75 / night

£499 - £595 / week

Book

from £75 / night

Distance approx 0.1 miles from Oak Island Harbor Show on Map

(13) Excellent 

1 / 59

Holiday townhouse with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 6 Min stay varies

Townhouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £85 / night

£350 - £1210 / week

Book

from £85 / night

Distance approx 0.1 miles from Oak Island Harbor Show on Map

(2) Excellent 

1 / 15

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £60 / night

£425 - £515 / week

Book

from £60 / night

Distance approx 0.23 miles from Oak Island Harbor Show on Map

(10) Excellent 

1 / 33

Villa rental in Kissimmee with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

Villa / 4 bedrooms / sleeps 9 / Min stay varies

Add to shortlist

from £82 / night

£540 - £660 / week

Book

from £82 / night

Distance approx 0.24 miles from Oak Island Harbor Show on Map

1 / 16

Holiday villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 7 nights min stay

Villa / 6 bedrooms / sleeps 14 / 7 nights min stay

Add to shortlist

from £114 / night

£795 - £1100 / week

Book

from £114 / night

Distance approx 1.96 miles from Oak Island Harbor Show on Map

(4) Very Good 

1 / 49

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min stay

Villa / 4 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £80 / night

£450 - £599 / week

Book

from £80 / night

Distance approx 2.28 miles from Oak Island Harbor Show on Map

(8) Excellent 

1 / 12

Holiday townhouse in Kissimmee

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

Townhouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £50 / night

£350 - £415 / week

Book

from £50 / night

Distance approx 2.47 miles from Oak Island Harbor Show on Map

(1) Excellent 

1 / 61

Holiday home in Kissimmee

Kissimmee / Venetian Bay Villages

3 6 4 nights min stay

House / 3 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £50 / night

£350 / week

Book

from £50 / night

Distance approx 2.52 miles from Oak Island Harbor Show on Map

1 / 26

Holiday townhouse with shared pool in Kissimmee

Kissimmee / Venetian Bay Villages

3 6 2 nights min stay

Townhouse / 3 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £56 / night

£390 - £560 / week

Book

from £56 / night

Distance approx 2.54 miles from Oak Island Harbor Show on Map

1 / 22

Holiday townhouse with golf nearby in Kissimmee

Kissimmee / Venetian Bay Villages

4 10 5 nights min stay

Townhouse / 4 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £72 / night

£499 - £624 / week

Book

from £72 / night

Distance approx 2.86 miles from Oak Island Harbor Show on Map

(24) Excellent 

1 / 32

Holiday apartment in Kissimmee

Central Florida / Kissimmee

3 8 4 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £83 / night

£463 / week

Book

from £83 / night

Distance approx 2.87 miles from Oak Island Harbor Show on Map

(6) Excellent 

1 / 19

Kissimmee holiday villa rental

Kissimmee / Creekside

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £70 / night

£490 / week

Enquire

from £70 / night

Distance approx 2.9 miles from Oak Island Harbor Show on Map

1 / 12

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 4 nights min stay

Villa / 3 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £83 / night

£463 / week

Book

from £83 / night

Distance approx 2.96 miles from Oak Island Harbor Show on Map

(3) Excellent 

1 / 65

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £70 / night

£450 - £600 / week

Book

from £70 / night

Distance approx 2.98 miles from Oak Island Harbor Show on Map

(26) Excellent 

1 / 41

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min stay

Villa / 3 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £80 / night

£495 - £505 / week

Book

from £80 / night

Distance approx 3.03 miles from Oak Island Harbor Show on Map

1 / 60

Holiday home with swimming pool, golf nearby in Orlando

Central Florida / Orlando

4 8 3 nights min stay

House / 4 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £90 / night

£624 / week

Book

from £90 / night

Distance approx 3.06 miles from Oak Island Harbor Show on Map

(1) Very Good 

1 / 18

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

4 9 7 nights min stay

Villa / 4 bedrooms / sleeps 9 / 7 nights min stay

Add to shortlist

from £85 / night

£595 - £750 / week

Book

from £85 / night

Distance approx 3.08 miles from Oak Island Harbor Show on Map

(56) Excellent 

1 / 24

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £70 / night

£465 - £580 / week

Book

from £70 / night

Distance approx 3.37 miles from Oak Island Harbor Show on Map

(1) Excellent 

1 / 23

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £165 / night

£1155 - £1435 / week

Book

from £165 / night

Distance approx 3.38 miles from Oak Island Harbor Show on Map

(1) Excellent 

1 / 20

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

7 16 Min stay varies

Villa / 7 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £150 / night

£1050 - £1250 / week

Book

from £150 / night

Distance approx 3.39 miles from Oak Island Harbor Show on Map

(17) Excellent 

1 / 18

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £61 / night

£425 - £495 / week

Enquire

from £61 / night

Distance approx 3.4 miles from Oak Island Harbor Show on Map

(5) Excellent 

1 / 13

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Point

4 8 4 nights min stay

Villa / 4 bedrooms / sleeps 8 / 4 nights min stay

Add to shortlist

from £75 / night

£525 / week

Book

from £75 / night

Distance approx 3.41 miles from Oak Island Harbor Show on Map

(15) Excellent 

1 / 24

Home rental in Kissimmee

Kissimmee / Bellavida Resort

6 13 7 nights min stay

House / 6 bedrooms / sleeps 13 / 7 nights min stay

Add to shortlist

from £171 / night

£1195 / week

Enquire

from £171 / night

Distance approx 3.42 miles from Oak Island Harbor Show on Map

(13) Excellent 

1 / 22

Holiday villa with swimming pool in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min stay

Villa / 4 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £100 / night

£635 - £825 / week

Book

from £100 / night

Distance approx 3.43 miles from Oak Island Harbor Show on Map

(5) Excellent 

1 / 36

Holiday apartment with swimming pool, golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £60 / night

£418 / week

Book

from £60 / night

Distance approx 3.44 miles from Oak Island Harbor Show on Map

(14) Excellent 

1 / 20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 2 nights min stay

Villa / 6 bedrooms / sleeps 12 / 2 nights min stay

Add to shortlist

from £175 / night

£1225 - £1645 / week

Enquire

from £175 / night

Distance approx 3.46 miles from Oak Island Harbor Show on Map

(13) Excellent 

1 / 23

Kissimmee holiday villa let

Kissimmee / Bellavida Resort

6 13 Min stay varies

Villa / 6 bedrooms / sleeps 13 / Min stay varies

Add to shortlist

from £169 / night

£1145 - £1445 / week

Book

from £169 / night

Distance approx 3.46 miles from Oak Island Harbor Show on Map

(22) Very Good 

1 / 20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 10 3 nights min stay

Villa / 4 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £77 / night

£538 - £617 / week

Book

from £77 / night

Distance approx 3.46 miles from Oak Island Harbor Show on Map

(8) Excellent 

1 / 14

Holiday townhouse in Kissimmee

Kissimmee / Bellavida Resort

3 6 Min stay varies

Townhouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

Pricing unknown

Enquire

Pricing unknown

Distance approx 3.49 miles from Oak Island Harbor Show on Map

(1) Excellent 

1 / 12

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 5 nights min stay

Villa / 4 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £66 / night

£465 / week

Enquire

from £66 / night

Distance approx 3.5 miles from Oak Island Harbor Show on Map

(2) Very Good 

1 / 20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £66 / night

£600 / week

Book

from £66 / night

Distance approx 3.5 miles from Oak Island Harbor Show on Map

1 / 17

Holiday townhouse accommodation

Central Florida / Kissimmee

4 10 Min stay varies

Townhouse / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £90 / night

£624 / week

Book

from £90 / night

Distance approx 3.5 miles from Oak Island Harbor Show on Map

1 / 30

Holiday home in Orlando

Central Florida / Orlando

4 10 3 nights min stay

House / 4 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £86 / night

£583 / week

Book

from £86 / night

Distance approx 3.52 miles from Oak Island Harbor Show on Map

1 / 17

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min stay

Villa / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £64 / night

£450 / week

Book

from £64 / night

Distance approx 3.52 miles from Oak Island Harbor Show on Map

(5) Excellent 

1 / 23

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £75 / night

£500 / week

Book

from £75 / night

Distance approx 3.53 miles from Oak Island Harbor Show on Map

(3) Very Good 

1 / 74

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

Villa / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £108 / night

£750 - £956 / week

Book

from £108 / night

Distance approx 3.54 miles from Oak Island Harbor Show on Map

(8) Excellent 

1 / 99

Kissimmee holiday villa rental

Kissimmee / Bellavida Resort

6 14 5 nights min stay

Villa / 6 bedrooms / sleeps 14 / 5 nights min stay

Add to shortlist

from £148 / night

£1031 - £1367 / week

Book

from £148 / night

Distance approx 3.55 miles from Oak Island Harbor Show on Map

1 / 33

Holiday townhouse rental

Kissimmee / Coral Cay

4 10 1 night min stay

Townhouse / 4 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £73 / night

£512 - £835 / week

Book

from £73 / night

Distance approx 3.56 miles from Oak Island Harbor Show on Map

1 / 15

Holiday townhouse in Kissimmee

Kissimmee / Bellavida Resort

4 8 Min stay varies

Townhouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £66 / night

£456 - £523 / week

Book

from £66 / night

Distance approx 3.59 miles from Oak Island Harbor Show on Map

(4) Very Good 

1 / 24

Kissimmee holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

House / 4 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £30 / night

£350 - £630 / week

Book

from £30 / night

Distance approx 3.6 miles from Oak Island Harbor Show on Map

1 / 37

Holiday townhouse in Kissimmee

Kissimmee / Coral Cay

4 10 1 night min stay

Townhouse / 4 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £73 / night

£512 - £835 / week

Book

from £73 / night

Distance approx 3.6 miles from Oak Island Harbor Show on Map

(28) Excellent 

1 / 24

Holiday townhouse with shared pool in Kissimmee

Kissimmee / Coral Cay

4 8 Min stay varies

Townhouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £50 / night

£350 / week

Enquire

from £50 / night

Distance approx 3.61 miles from Oak Island Harbor Show on Map

1 / 35

Townhouse rental in Kissimmee

Kissimmee / Coral Cay

4 10 1 night min stay

Townhouse / 4 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £73 / night

£512 - £835 / week

Book

from £73 / night

Distance approx 3.62 miles from Oak Island Harbor Show on Map

(2) Very Good 

1 / 29

Holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £48 / night

£336 - £768 / week

Book

from £48 / night

Distance approx 3.63 miles from Oak Island Harbor Show on Map

1 / 32

Holiday townhouse rental

Kissimmee / Coral Cay

4 10 1 night min stay

Townhouse / 4 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £73 / night

£512 - £835 / week

Book

from £73 / night

Distance approx 3.63 miles from Oak Island Harbor Show on Map

(12) Excellent 

1 / 24

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £90 / night

£580 - £800 / week

Enquire

from £90 / night

Distance approx 3.66 miles from Oak Island Harbor Show on Map

1 / 19

Holiday villa in Orlando

Central Florida / Orlando

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £90 / night

£595 / week

Book

from £90 / night

Distance approx 3.67 miles from Oak Island Harbor Show on Map

(2) Excellent 

1 / 24

Holiday villa with indoor pool in Kissimmee

Kissimmee / Lake Berkley

6 14 Min stay varies

Villa / 6 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £133 / night

£857 - £1036 / week

Book

from £133 / night

Distance approx 3.68 miles from Oak Island Harbor Show on Map

1 / 13

Villa rental in Kissimmee

Kissimmee / Lake Berkley

4 10 5 nights min stay

Villa / 4 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £90 / night

£658 / week

Book

from £90 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page