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66 Vacation rentals

Vacation condo with shared pool, golf nearby in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $445 / night

$3,110 / week

1 / 8

Vacation home with shared pool in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $995 / night

$6,965 / week

1 / 49

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $974 / night

$6,813 / week

1 / 21

Vacation villa with swimming pool in Wailea

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,350 / night

$9,450 / week

1 / 50

Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,195 / night

$15,365 / week

1 / 50

Vacation villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,295 / night

$9,065 / week

1 / 48

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $625 / night

$4,075 / week

1 / 31

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,218 / night

$5,903 / week

1 / 54

Condo rental in Wailea with shared pool

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $447 / night

$3,126 / week

1 / 15

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,088 / night

$7,615 / week

1 / 33

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $625 / night

$4,075 / week

1 / 43

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $977 / night

$4,680 / week

1 / 58

Vacation apartment in Wailea

Wailea apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $675 / night

$4,275 / week

1 / 52

Vacation home in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,199 / night

$8,393 / week

1 / 50

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $224 / night

$1,518 - $1,941 / week

1 / 16

Vacation apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $1,775 / night

$8,476 / week

1 / 40

Home rental in Wailea with swimming pool

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,995 / night

$13,965 / week

1 / 48

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $465 / night

$3,255 / week

1 / 40

Vacation condo with shared pool in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $725 / night

$4,725 / week

1 / 51

Wailea Vacation villa rental

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,099 / night

$7,693 / week

1 / 50

Villa rental in Wailea with shared pool

Wailea villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,349 / night

$9,443 / week

1 / 49

Vacation home rental

Wailea house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,325 / night

$9,275 / week

1 / 50

Vacation villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $999 / night

$6,993 / week

1 / 50

Wailea Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $999 / night

$6,993 / week

1 / 50

Vacation apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,036 / night

$5,717 / week

1 / 52

Wailea Vacation apartment rental

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,041 / night

$4,971 / week

1 / 25

Wailea Vacation villa rental

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,395 / night

$9,765 / week

1 / 49

Wailea Vacation villa rental

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $999 / night

$6,993 / week

1 / 50

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $1,607 / night

$7,695 / week

1 / 53

Vacation condo with shared pool in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $495 / night

$3,465 / week

1 / 29

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,195 / night

$8,365 / week

1 / 50

Vacation villa with shared pool in Wailea

Wailea villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,199 / night

$8,393 / week

1 / 49

Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $1,349 / night

$9,443 / week

1 / 48

Vacation villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,095 / night

$7,665 / week

1 / 50

Wailea Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,095 / night

$7,665 / week

1 / 49

Vacation villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $2,895 / night

$20,265 / week

1 / 50

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,071 / night

$5,906 / week

1 / 45

Vacation apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $600 / night

$3,892 / week

1 / 38

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,169 / night

$6,120 / week

1 / 48

Vacation apartment accommodation

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,140 / night

$5,460 / week

1 / 36