Updating

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

Updating

Best Wailea Condos on Holiday Lettings - Vacation rentals

All filters

Filters

347 Vacation rentals

Revenue impacts this sort order. Learn more

Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $455 / night

$3,185 / week

1 / 21

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $501 / night

$3,507 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $405 / night

$2,835 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $528 / night

$3,696 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $770 / night

$5,390 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $352 / night

$2,464 / week

1 / 30

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $406 / night

$2,842 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $768 / night

$5,376 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $484 / night

$3,388 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $190 / night

$1,330 / week

1 / 19

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $716 / night

$5,012 / week

1 / 29

Condo rental in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $613 / night

$4,291 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $474 / night

$3,318 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $211 / night

$1,477 / week

1 / 24

Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $410 / night

$2,870 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $944 / night

$6,608 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from $420 / night

$2,940 / week

1 / 30

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $428 / night

$2,996 / week

1 / 30

Ski condo to rent in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $396 / night

$2,772 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $509 / night

$3,563 / week

1 / 30

Villa rental in Wailea

Wailea villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $1,999 / night

$13,993 / week

1 / 25

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $502 / night

$3,514 / 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 $1,322 / night

$9,254 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $500 / night

$3,500 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,384 / night

$9,688 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $478 / night

$3,346 / week

1 / 30

Condo accommodation in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $437 / night

$3,059 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $666 / night

$4,662 / week

1 / 30

Vacation home in Wailea

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,433 / night

$10,031 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $541 / night

$3,787 / week

1 / 22

Vacation condo in Wailea

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $542 / night

$3,794 / week

1 / 30

Wailea Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $401 / night

$2,807 / week

1 / 30

Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $648 / night

$4,536 / week

1 / 24

Vacation condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $498 / night

$3,486 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $333 / night

$2,331 / week

1 / 30

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $605 / night

$4,235 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $979 / night

$6,853 / week

1 / 19

Wailea Vacation condo rental

Wailea condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $378 / night

$2,646 / week

1 / 30

Vacation condo in Wailea

Wailea condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $863 / night

$6,041 / week

1 / 30