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Wailea Vacation Rentals & Apartments - 410 Rentals Available

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410 Vacation rentals

(98)

1 / 42

Wailea Villa

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

$895.00

Excellent (98 reviews)

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from $895.00 / night

1 / 20

Wailea Condo

  • 2
  • 6
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$159.00

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from $159.00 / night

(10)

1 / 16

Wailea Apartment

  • 1
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$299.00

Excellent (10 reviews)

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from $299.00 / night

1 / 15

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$486.00

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from $486.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$426.00

Excellent (7 reviews)

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from $426.00 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Excellent (4 reviews)

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from $612.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$699.00

Excellent (1 reviews)

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from $699.00 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$384.00

Very Good (4 reviews)

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from $384.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$267.00

Excellent (1 reviews)

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from $267.00 / night

(3)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children
  • Ask about pets

$266.00

Very Good (3 reviews)

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from $266.00 / night

1 / 20

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$440.00

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from $440.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$490.00

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from $490.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Ask about children
  • Ask about pets

$1,166.00

Excellent (12 reviews)

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from $1,166.00 / night

(17)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$384.00

Excellent (17 reviews)

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from $384.00 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$599.00

Excellent (4 reviews)

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from $599.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Inquire

from $612.00 / night

(13)

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$250.00

Very Good (13 reviews)

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from $250.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$384.00

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from $384.00 / night

(17)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children
  • Ask about pets

$420.00

Very Good (17 reviews)

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from $420.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$384.00

Excellent (7 reviews)

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from $384.00 / night

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$198.00

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from $198.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$775.00

Excellent (1 reviews)

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from $775.00 / night

(5)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Very Good (5 reviews)

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from $540.00 / night

(9)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$384.00

Very Good (9 reviews)

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from $384.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (7 reviews)

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$440.00

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from $440.00 / night

(16)

1 / 16

Wailea Apartment

  • 1
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$375.00

Very Good (16 reviews)

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from $375.00 / night

(8)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$486.00

Very Good (8 reviews)

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from $486.00 / night

(3)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$750.00

Very Good (3 reviews)

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from $750.00 / night

(2)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Excellent (2 reviews)

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from $540.00 / night

(11)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$599.00

Very Good (11 reviews)

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from $599.00 / night

(20)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$447.00

Very Good (20 reviews)

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from $447.00 / night

(1)

1 / 23

Wailea Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

$199.00

Excellent (1 reviews)

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from $199.00 / night

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children
  • Ask about pets

$293.00

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from $293.00 / night

1 / 23

Wailea Villa

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

$1,649.00

Book

from $1,649.00 / night

(16)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Excellent (16 reviews)

Inquire

from $540.00 / night

(22)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children
  • Ask about pets

$525.00

Very Good (22 reviews)

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from $525.00 / night

(14)

1 / 16

Wailea Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (14 reviews)

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

$419.00

Inquire

from $419.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$200.00

Inquire

from $200.00 / night