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Wailea Vacation Rentals & Apartments - 514 Rentals Available

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514 Vacation rentals

(101)

1 / 42

Wailea Villa

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

$995.00

Excellent (101 reviews)

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from $995.00 / night

1 / 20

Wailea Condo

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

Responds fast! Avg. 3 hours 5 minutes

$159.00

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from $159.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • min stay varies
  • Ask about children
  • Ask about pets

$419.00

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from $419.00 / night

(1)

1 / 50

Wailea House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,700.00

Excellent (1 reviews)

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from $2,700.00 / night

(16)

1 / 16

Wailea Apartment

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

$399.00

Very Good (16 reviews)

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from $399.00 / 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

(1)

1 / 15

Wailea Villa

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning

$1,695.00

Excellent (1 reviews)

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from $1,695.00 / night

(2)

1 / 24

Wailea Villa

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 29 minutes

$2,700.00

Very Good (2 reviews)

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from $2,700.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$339.00

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from $339.00 / night

(13)

1 / 16

Wailea Apartment

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

$229.00

Very Good (13 reviews)

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from $229.00 / night

1 / 16

Wailea Apartment

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$189.00

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from $189.00 / night

(10)

1 / 16

Wailea Apartment

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

$279.00

Excellent (10 reviews)

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from $279.00 / night

(17)

1 / 16

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$339.00

Excellent (17 reviews)

Inquire

from $339.00 / night

1 / 16

Wailea Apartment

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

$539.00

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from $539.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$370.00

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from $370.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

$1,569.00

Excellent (12 reviews)

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from $1,569.00 / night

1 / 50

Wailea House

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

$995.00

Inquire

from $995.00 / night

(5)

1 / 50

Wailea House

  • 4
  • 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,345.00

Excellent (5 reviews)

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from $1,345.00 / night

(6)

1 / 50

Wailea House

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,650.00

Excellent (6 reviews)

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from $1,650.00 / night

(1)

1 / 50

Wailea Villa

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

$1,025.00

Excellent (1 reviews)

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from $1,025.00 / night

1 / 5

Wailea Apartment

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

$399.00

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from $399.00 / night

(10)

1 / 50

Wailea Villa

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

$925.00

Excellent (10 reviews)

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from $925.00 / night

(7)

1 / 16

Wailea Apartment

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

$410.00

Excellent (7 reviews)

Inquire

from $410.00 / night

1 / 16

Wailea Apartment

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

$189.00

Inquire

from $189.00 / night

(9)

1 / 16

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$383.00

Very Good (9 reviews)

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from $383.00 / night

(2)

1 / 16

Wailea Apartment

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

$499.00

Excellent (2 reviews)

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from $499.00 / night

(2)

1 / 50

Wailea House

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

$1,045.00

Excellent (2 reviews)

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from $1,045.00 / night

(11)

1 / 16

Wailea Apartment

  • 2
  • 5
  • min stay varies
  • Ask about children
  • Ask about pets

$599.00

Very Good (11 reviews)

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from $599.00 / night

(17)

1 / 16

Wailea Apartment

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

$420.00

Very Good (17 reviews)

Inquire

from $420.00 / night

1 / 16

Wailea Apartment

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

$486.00

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from $486.00 / night

(2)

1 / 16

Wailea Apartment

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

$219.00

Very Good (2 reviews)

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from $219.00 / night

(4)

1 / 16

Wailea Apartment

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

$619.00

Excellent (4 reviews)

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from $619.00 / night

(10)

1 / 16

Wailea Apartment

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

$199.00

Very Good (10 reviews)

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from $199.00 / night

(16)

1 / 16

Wailea Apartment

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

$529.00

Excellent (16 reviews)

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from $529.00 / night

(2)

1 / 50

Wailea Villa

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

$995.00

Excellent (2 reviews)

Inquire

from $995.00 / night

(3)

1 / 16

Wailea Apartment

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

$239.00

Very Good (3 reviews)

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from $239.00 / night

1 / 34

Wailea Condo

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

$295.00

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from $295.00 / night

(13)

1 / 40

Wailea House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,095.00

Excellent (13 reviews)

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from $1,095.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$440.00

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from $440.00 / 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