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Wailea Vacation Rentals & Apartments - 330 Rentals Available

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330 Vacation rentals

(3)

1 / 10

Wailea Apartment

  • 1
  • 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 2 minutes

$225.00

Very Good (3 reviews)

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from $225.00 / night

1 / 24

Wailea House

  • 5
  • 8
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$2,163.00

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from $2,163.00 / night

1 / 20

Wailea Condo

  • 2
  • 6
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 9 minutes

$204.00

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from $204.00 / night

(101)

1 / 42

Wailea Villa

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,140.00

Excellent (101 reviews)

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from $1,140.00 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$762.00

Excellent (4 reviews)

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from $762.00 / night

(2)

1 / 50

Wailea House

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,195.00

Excellent (2 reviews)

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from $1,195.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$762.00

Very Good (7 reviews)

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from $762.00 / night

(5)

1 / 16

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$335.00

Excellent (5 reviews)

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from $335.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$479.00

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from $479.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Ask about children
  • Ask about pets

$409.00

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from $409.00 / night

(7)

1 / 8

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$399.00

Excellent (7 reviews)

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from $399.00 / night

(2)

1 / 16

Wailea Apartment

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$265.00

Very Good (2 reviews)

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from $265.00 / night

(13)

1 / 16

Wailea Apartment

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$165.00

Average (13 reviews)

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from $165.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$690.00

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from $690.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$189.00

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from $189.00 / night

1 / 15

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$762.00

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from $762.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$690.00

Excellent (1 reviews)

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from $690.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$399.00

Inquire

from $399.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$302.00

Excellent (1 reviews)

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from $302.00 / night

(16)

1 / 16

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$409.00

Very Good (16 reviews)

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from $409.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$419.00

Inquire

from $419.00 / night

1 / 15

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$799.00

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from $799.00 / night

(20)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$629.00

Very Good (20 reviews)

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from $629.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$380.00

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from $380.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$899.00

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from $899.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$899.00

Excellent (1 reviews)

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from $899.00 / night

(8)

1 / 10

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$690.00

Very Good (8 reviews)

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from $690.00 / night

(13)

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$229.00

Very Good (13 reviews)

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from $229.00 / night

(8)

1 / 50

Wailea Villa

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,195.00

Excellent (8 reviews)

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from $1,195.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$419.00

Inquire

from $419.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$299.00

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from $299.00 / night

1 / 15

Wailea Condo

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

$295.00

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from $295.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$389.00

Excellent (7 reviews)

Inquire

from $389.00 / night

(17)

1 / 9

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$419.00

Excellent (17 reviews)

Inquire

from $419.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$419.00

Inquire

from $419.00 / night

(9)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$419.00

Very Good (9 reviews)

Inquire

from $419.00 / night

(2)

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$690.00

Excellent (2 reviews)

Inquire

from $690.00 / night

(1)

1 / 16

Wailea Apartment

  • 4
  • 8
  • 5 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

$1,349.00

Excellent (1 reviews)

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from $1,349.00 / night

(1)

1 / 50

Wailea House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,796.00

Excellent (1 reviews)

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from $1,796.00 / night

1 / 50

Wailea House

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,850.00

Inquire

from $2,850.00 / night