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Wailea Vacation Rentals & Apartments - 279 Rentals Available

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279 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

(5)

1 / 24

Wailea House

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

$1,195.00

Excellent (5 reviews)

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from $1,195.00 / 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

(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)

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

(7)

1 / 24

Wailea Villa

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

$995.00

Excellent (7 reviews)

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from $995.00 / night

1 / 24

Wailea House

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

$1,045.00

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from $1,045.00 / night

(6)

1 / 24

Wailea House

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

$1,695.00

Excellent (6 reviews)

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from $1,695.00 / night

(2)

1 / 24

Wailea Villa

  • 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

(2)

1 / 24

Wailea House

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

$1,195.00

Excellent (2 reviews)

Inquire

from $1,195.00 / night

1 / 23

Wailea House

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

$2,095.00

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from $2,095.00 / night

(7)

1 / 24

Wailea House

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

$1,045.00

Excellent (7 reviews)

Inquire

from $1,045.00 / night

(13)

1 / 23

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

(2)

1 / 24

Wailea Villa

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

$995.00

Excellent (2 reviews)

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from $995.00 / night

(6)

1 / 24

Wailea Villa

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

$2,250.00

Excellent (6 reviews)

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from $2,250.00 / night

(1)

1 / 24

Wailea House

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

$1,695.00

Excellent (1 reviews)

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from $1,695.00 / night

(8)

1 / 24

Wailea Villa

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

$995.00

Excellent (8 reviews)

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from $995.00 / night

(14)

1 / 24

Wailea Villa

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

$825.00

Excellent (14 reviews)

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from $825.00 / night

(2)

1 / 24

Wailea Villa

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

$2,700.00

Very Good (2 reviews)

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from $2,700.00 / night

(1)

1 / 24

Wailea Villa

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

$1,295.00

Excellent (1 reviews)

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from $1,295.00 / night

(11)

1 / 24

Wailea Villa

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

$1,595.00

Excellent (11 reviews)

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from $1,595.00 / night

(9)

1 / 24

Wailea Villa

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

$1,545.00

Excellent (9 reviews)

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from $1,545.00 / night

(1)

1 / 24

Wailea Villa

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

$1,396.00

Excellent (1 reviews)

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from $1,396.00 / night

(9)

1 / 24

Wailea Villa

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

$1,695.00

Excellent (9 reviews)

Inquire

from $1,695.00 / night

(3)

1 / 24

Wailea Villa

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

$1,650.00

Very Good (3 reviews)

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from $1,650.00 / night

(2)

1 / 24

Wailea House

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

$1,695.00

Very Good (2 reviews)

Inquire

from $1,695.00 / night

(10)

1 / 24

Wailea Villa

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

$995.00

Excellent (10 reviews)

Inquire

from $995.00 / night

1 / 24

Wailea House

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

$2,700.00

Inquire

from $2,700.00 / night

(1)

1 / 50

Wailea House

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

$2,700.00

Excellent (1 reviews)

Inquire

from $2,700.00 / night

1 / 33

Wailea Condo

  • 2
  • 6
  • Min stay varies
  • Child friendly

$179.00

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from $179.00 / night

(13)

1 / 24

Wailea House

  • 5
  • 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,950.00

Very Good (13 reviews)

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from $2,950.00 / night

(4)

1 / 24

Wailea House

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

$1,350.00

Very Good (4 reviews)

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from $1,350.00 / night

1 / 25

Wailea Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Air conditioning

$1,327.00

Book

from $1,327.00 / night

1 / 23

Wailea Villa

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Air conditioning

$1,649.00

Book

from $1,649.00 / night