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Wailea Vacation Rentals & Apartments with Swimming Pool - 293 Rentals Available.

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293 Vacation rentals

Filters applied: Swimming pool

(3)

1 / 10

Wailea Apartment

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

$185.00

Very Good (3 reviews)

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from $185.00 / 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 28 minutes

$183.00

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from $183.00 / night

(101)

1 / 42

Wailea Villa

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

Responds fast! Avg. 1 hour 43 minutes

$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

$689.00

Excellent (4 reviews)

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from $689.00 / night

(13)

1 / 0

Wailea House

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$895.00

Excellent (13 reviews)

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from $895.00 / night

(2)

1 / 16

Wailea Apartment

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

$236.00

Very Good (2 reviews)

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from $236.00 / night

(2)

1 / 50

Wailea House

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

$1,195.00

Excellent (2 reviews)

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from $1,195.00 / night

(5)

1 / 16

Wailea Apartment

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

$279.00

Excellent (5 reviews)

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from $279.00 / night

(7)

1 / 8

Wailea Apartment

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

$379.00

Excellent (7 reviews)

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from $379.00 / night

(7)

1 / 16

Wailea Apartment

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

$612.00

Very Good (7 reviews)

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from $612.00 / night

1 / 16

Wailea Apartment

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

$669.00

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from $669.00 / night

1 / 16

Wailea Apartment

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

$440.00

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from $440.00 / night

1 / 15

Wailea Apartment

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

$549.00

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from $549.00 / night

1 / 16

Wailea Apartment

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

$399.00

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from $399.00 / 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)

1 / 16

Wailea Apartment

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$269.00

Excellent (1 reviews)

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from $269.00 / night

(13)

1 / 16

Wailea Apartment

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

$239.00

Very Good (13 reviews)

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from $239.00 / night

1 / 16

Wailea Apartment

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

$690.00

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from $690.00 / night

(17)

1 / 9

Wailea Apartment

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

$409.00

Excellent (17 reviews)

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from $409.00 / night

1 / 16

Wailea Apartment

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

$399.00

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from $399.00 / night

1 / 15

Wailea Apartment

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

$749.00

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from $749.00 / night

(20)

1 / 16

Wailea Apartment

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

$449.00

Very Good (20 reviews)

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from $449.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$189.00

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from $189.00 / night

1 / 16

Wailea Apartment

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

$349.00

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from $349.00 / night

1 / 16

Wailea Apartment

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

$390.00

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from $390.00 / night

1 / 16

Wailea Apartment

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

$265.00

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from $265.00 / night

1 / 16

Wailea Apartment

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

$830.00

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from $830.00 / night

(9)

1 / 16

Wailea Apartment

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

$399.00

Very Good (9 reviews)

Inquire

from $399.00 / night

1 / 16

Wailea Apartment

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

$409.00

Inquire

from $409.00 / night

(8)

1 / 50

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

1 / 5

Wailea Apartment

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$399.00

Inquire

from $399.00 / night

(16)

1 / 16

Wailea Apartment

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

$399.00

Very Good (16 reviews)

Inquire

from $399.00 / night

1 / 16

Wailea Apartment

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

$899.00

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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 / 50

Wailea House

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

$3,050.00

Very Good (13 reviews)

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from $3,050.00 / 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

1 / 15

Wailea Apartment

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

$719.00

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from $719.00 / night

(1)

1 / 16

Wailea Apartment

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

$595.00

Excellent (1 reviews)

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from $595.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$1,499.00

Excellent (12 reviews)

Inquire

from $1,499.00 / night