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Best Wailea Condos on Holiday Lettings - Vacation rentals

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351 Vacation rentals

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Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $402 / night

$2,814 / week

1 / 23

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $640 / night

$4,480 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $459 / night

$3,213 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $617 / night

$4,319 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $890 / night

$6,230 / week

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Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $428 / night

$2,996 / week

1 / 30

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $505 / night

$3,535 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $862 / night

$6,034 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $561 / night

$3,927 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $186 / night

$1,302 / week

1 / 19

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $427 / night

$2,989 / week

1 / 29

Condo rental in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $469 / night

$3,283 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $523 / night

$3,661 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $218 / night

$1,526 / week

1 / 24

Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $434 / night

$3,038 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $931 / night

$6,517 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from $446 / night

$3,122 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $524 / night

$3,668 / week

1 / 30

Condo accommodation in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $526 / night

$3,682 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $596 / night

$4,172 / week

1 / 30

Villa rental in Wailea

Wailea villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $2,176 / night

$15,232 / week

1 / 25

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $554 / night

$3,878 / week

1 / 30

Wailea ski condo to rent.

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $674 / night

$4,718 / week

1 / 30

Wailea Vacation villa rental

Wailea villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $1,562 / night

$10,934 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $474 / night

$3,318 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,294 / night

$9,058 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $626 / night

$4,382 / week

1 / 30

Condo accommodation in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $560 / night

$3,920 / week

1 / 30

Wailea ski condo to rent.

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $701 / night

$4,907 / week

1 / 30

Vacation home in Wailea

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,523 / night

$10,661 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $542 / night

$3,794 / week

1 / 22

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $621 / night

$4,347 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $456 / night

$3,192 / week

1 / 30

Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $630 / night

$4,410 / week

1 / 24

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $595 / night

$4,165 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $327 / night

$2,289 / week

1 / 30

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $589 / night

$4,123 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $676 / night

$4,732 / week

1 / 19

Wailea Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $466 / night

$3,262 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $936 / night

$6,552 / week

1 / 30