Updating

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

Updating

All filters

Filters (1)

Clear filters

26 Vacation rentals

Applied filters (1)

Vacation home with shared pool in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $995 / night

$6,965 / week

1 / 49

Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,195 / night

$15,365 / week

1 / 50

Vacation home rental

Wailea house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from $2,395 / night

$16,765 / week

1 / 50

Vacation home in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,199 / night

$8,393 / week

1 / 50

Vacation home in Wailea

Wailea house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $895 / night

$6,265 / week

1 / 43

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 home rental

Wailea house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,325 / night

$9,275 / week

1 / 50

Wailea Vacation home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $999 / night

$6,993 / 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 home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $1,349 / night

$9,443 / week

1 / 48

Vacation home rental

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $2,000 / night

$14,000 / week

1 / 46

Wailea Vacation home rental

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $469 / night

$3,283 / week

1 / 26

Wailea Vacation home rental

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $399 / night

$2,793 / week

1 / 32

Vacation home with golf nearby in Wailea

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $339 / night

$2,373 / week

1 / 36

Wailea Vacation home rental

Wailea house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $329 / night

$2,303 / week

1 / 22

Vacation home with golf nearby in Wailea

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $599 / night

$4,193 / week

1 / 51

Vacation home with golf nearby in Wailea

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $509 / night

$3,563 / week

1 / 45

Wailea Vacation home accommodation

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $549 / night

$3,843 / week

1 / 53

Vacation home with golf nearby in Wailea

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $499 / night

$3,493 / week

1 / 52

Wailea Vacation home rental

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $779 / night

$5,453 / week

1 / 51

Vacation home with golf nearby in Wailea

Wailea house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $639 / night

$4,473 / week

1 / 44

Wailea Vacation home rental

Wailea house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $749 / night

$5,243 / week

1 / 38

Wailea Vacation home rental

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $349 / night

$2,443 / week

1 / 36

Wailea Vacation home rental

Wailea house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $729 / night

$5,103 / week

1 / 37

Vacation home with golf nearby in Wailea

Wailea house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $569 / night

$3,983 / week

1 / 37

Vacation home with golf nearby in Wailea

Wailea house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $569 / night

$3,983 / week

1 / 45

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Lahaina

Lahaina house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,592 / night

$11,141 / week

1 / 48

Kihei Vacation home rental

Kihei house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $509 / night

$5,089 - $5,249 / week

1 / 34

Kihei ski home to rent.

Kihei house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,031 / night

$7,214 / week

1 / 50

Vacation home rental

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $4,403 / night

$30,818 / week

1 / 28

Vacation home in Kihei

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $5,548 / night

$38,833 / week

1 / 27

Vacation home in Kihei

Kihei house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $915 / night

$6,404 / week

1 / 21

Vacation home in Makawao

Makawao house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $1,117 / night

$7,815 / week

1 / 30

Home rental in Haiku

Haiku house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $344 / night

$2,405 / week

1 / 8

Vacation home in Kihei

Kihei house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $2,519 / night

$17,633 / week

1 / 14

Paia Vacation home rental

Paia house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $974 / night

$4,609 / week

1 / 12

Vacation home with swimming pool in Kihei

Kihei house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,821 / night

$12,744 / week

1 / 45

Vacation home with swimming pool in Haiku

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,031 / night

$7,214 / week

1 / 26

Vacation home in Paia

Paia house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $606 / night

$4,240 / week

1 / 37

Vacation home in Paia

Paia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $304 / night

$2,124 / week

1 / 9