Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Best Vacation Rentals in Kalaheo - Holiday Lettings - Cabins

All filters

Filters

80 Vacation rentals

Great rentals within 20 miles that match your search

Condo rental in Poipu

Poipu condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $457 / night

$3,198 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $573 / night

$4,008 / week

1 / 9

Great rentals within 20 miles that match your search

Poipu Vacation home rental

Poipu house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $745 / night

$5,210 / week

1 / 43

Great rentals within 20 miles that match your search

Koloa Vacation studio rental

Koloa studio

  • Studio
  • 2 bathrooms
  • sleeps 2

from $361 / night

$2,525 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Koloa

Koloa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $3,819 / night

$26,730 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Poipu

Poipu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $630 / night

$4,409 / week

1 / 61

Great rentals within 20 miles that match your search

Condo rental in Poipu with shared pool

Poipu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $376 / night

$2,629 / week

1 / 15

Great rentals within 20 miles that match your search

Home rental in Poipu

Poipu house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

from $1,718 / night

$11,450 - $13,414 / week

1 / 22

Great rentals within 20 miles that match your search

Koloa Vacation condo rental

Koloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $205 / night

$1,435 / week

1 / 54

Great rentals within 20 miles that match your search

Vacation apartment in Poipu

Poipu apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $453 / night

$3,166 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,260 / night

$8,817 / week

1 / 31

Great rentals within 20 miles that match your search

Vacation villa with shared pool in Poipu

Poipu villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $724 / night

$5,066 / week

1 / 16

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $1,374 / night

$9,389 / week

1 / 32

Great rentals within 20 miles that match your search

Vacation condo in Koloa

Koloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $315 / night

$2,205 / week

1 / 28

Great rentals within 20 miles that match your search

Poipu Vacation apartment rental

Poipu apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $745 / night

$5,210 / week

1 / 35

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $630 / night

$4,411 / week

1 / 14

Great rentals within 20 miles that match your search

Villa rental in Poipu with shared pool

Poipu villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $581 / night

$4,064 - $15,654 / week

1 / 17

Great rentals within 20 miles that match your search

Poipu Vacation condo rental

Poipu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $315 / night

$2,205 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,110 / night

$6,950 / week

1 / 40

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Poipu

Poipu house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

from $2,620 / night

$18,339 / week

1 / 33

Great rentals within 20 miles that match your search

Vacation home in Poipu

Poipu house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $539 / night

$3,770 / week

1 / 11

Great rentals within 20 miles that match your search

Poipu Vacation condo rental

Poipu condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $573 / night

$4,008 / week

1 / 23

Great rentals within 20 miles that match your search

Poipu Vacation condo accommodation

Poipu condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $373 / night

$2,605 / week

1 / 26

Great rentals within 20 miles that match your search

Condo rental in Poipu with shared pool, golf nearby

Poipu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $851 / night

$5,956 / week

1 / 31

Great rentals within 20 miles that match your search

Condo rental in Poipu with shared pool, golf nearby

Poipu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $746 / night

$5,218 / week

1 / 31

Great rentals within 20 miles that match your search

Condo rental in Poipu with shared pool, golf nearby

Poipu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $746 / night

$5,218 / week

1 / 31

Great rentals within 20 miles that match your search

Vacation condo in Poipu

Poipu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $373 / night

$2,605 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation home in Koloa

Koloa house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $1,019 / night

$7,134 / week

1 / 43

Great rentals within 20 miles that match your search

Koloa Vacation condo rental

Koloa condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $338 / night

$2,365 / week

1 / 25

Great rentals within 20 miles that match your search

Condo rental in Koloa with shared pool

Koloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $225 / night

$1,572 - $2,625 / week

1 / 46

Great rentals within 20 miles that match your search

Koloa Vacation home rental

Koloa house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $682 / night

$4,769 / week

1 / 33

Great rentals within 20 miles that match your search

Vacation home with shared pool in Poipu

Poipu house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $516 / night

$3,607 / week

1 / 35

Great rentals within 20 miles that match your search

Koloa Vacation villa rental

Koloa villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $788 / night

$5,515 - $16,191 / week

1 / 48

Great rentals within 20 miles that match your search

Vacation condo in Koloa

Koloa condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $287 / night

$2,004 / week

1 / 26

Great rentals within 20 miles that match your search

Home rental in Koloa with shared pool

Koloa house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $453 / night

$3,166 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Poipu

Poipu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $572 / night

$4,000 / week

1 / 37

Great rentals within 20 miles that match your search

Condo rental in Koloa

Koloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $258 / night

$1,804 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Koloa

Koloa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from $258 / night

$1,804 / week

1 / 23

Great rentals within 20 miles that match your search

Poipu Vacation home rental

Poipu house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $504 / night

$3,527 / week

1 / 32

Great rentals within 20 miles that match your search

Koloa Vacation home rental

Koloa house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $630 / night

$4,409 / week

1 / 31