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Wailea Vacation Rentals & Apartments with Swimming Pool - 198 Rentals Available.

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198 Vacation rentals

Filters applied: Swimming pool

(98)

1 / 42

Wailea Villa

  • 3
  • 8
  • 5 nights min
  • 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

(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

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$662.00

Very Good (7 reviews)

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from $662.00 / night

1 / 16

Wailea Apartment

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

$529.00

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from $529.00 / night

(3)

1 / 16

Wailea Apartment

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

$675.00

Very Good (3 reviews)

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from $675.00 / night

1 / 16

Wailea Apartment

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

$200.00

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from $200.00 / 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

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

(1)

1 / 16

Wailea Apartment

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

$292.00

Excellent (1 reviews)

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from $292.00 / night

(1)

1 / 16

Wailea Apartment

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

$559.00

Excellent (1 reviews)

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from $559.00 / night

(16)

1 / 16

Wailea Apartment

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

$529.00

Excellent (16 reviews)

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from $529.00 / night

1 / 23

Wailea Villa

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

$1,649.00

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from $1,649.00 / night

(15)

1 / 16

Wailea Apartment

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

$649.00

Very Good (15 reviews)

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from $649.00 / night

(10)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 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

1 / 16

Wailea Apartment

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

$589.00

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from $589.00 / 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

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$662.00

Excellent (4 reviews)

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from $662.00 / night

(7)

1 / 16

Wailea Apartment

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

$662.00

Very Good (7 reviews)

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from $662.00 / 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

(2)

1 / 16

Wailea Apartment

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

$589.00

Excellent (2 reviews)

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from $589.00 / night

(5)

1 / 16

Wailea Apartment

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

$590.00

Very Good (5 reviews)

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from $590.00 / night

(20)

1 / 16

Wailea Apartment

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

$497.00

Very Good (20 reviews)

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from $497.00 / 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

1 / 16

Wailea Apartment

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

$189.00

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from $189.00 / night

1 / 16

Wailea Apartment

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

$525.00

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from $525.00 / night

(7)

1 / 16

Wailea Apartment

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

$649.00

Very Good (7 reviews)

Inquire

from $649.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$662.00

Inquire

from $662.00 / night

1 / 16

Wailea Apartment

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

$265.00

Inquire

from $265.00 / night

1 / 16

Wailea Apartment

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

$379.00

Inquire

from $379.00 / night

1 / 16

Wailea Apartment

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

$775.00

Inquire

from $775.00 / night

1 / 16

Wailea Apartment

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

$809.00

Inquire

from $809.00 / night

1 / 16

Wailea Apartment

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

$662.00

Inquire

from $662.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$497.00

Inquire

from $497.00 / night

1 / 25

Wailea Villa

  • 3
  • 6
  • 3 nights min
  • Swimming pool
  • Air conditioning

$2,599.00

Book

from $2,599.00 / night