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Wailea Vacation Rentals & Apartments with Swimming Pool - 238 Rentals Available.

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238 Vacation rentals

Filters applied: Swimming pool

(99)

1 / 42

Wailea Villa

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

$896.00

Excellent (99 reviews)

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from $896.00 / 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

(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

1 / 17

Wailea Condo

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

$145.00

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from $145.00 / night

(2)

1 / 50

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

(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 / 50

Wailea House

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

$1,595.00

Excellent (1 reviews)

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from $1,595.00 / 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)

1 / 16

Wailea Apartment

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

$775.00

Excellent (1 reviews)

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from $775.00 / night

(9)

1 / 50

Wailea Villa

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

$1,695.00

Excellent (9 reviews)

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from $1,695.00 / night

(1)

1 / 50

Wailea House

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

$2,701.00

Excellent (1 reviews)

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from $2,701.00 / night

(3)

1 / 50

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

1 / 50

Wailea House

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

$2,600.00

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from $2,600.00 / 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

(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 / 50

Wailea House

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

$995.00

Inquire

from $995.00 / night

1 / 16

Wailea Apartment

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

$149.00

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from $149.00 / night

(1)

1 / 16

Wailea Apartment

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

$292.00

Excellent (1 reviews)

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from $292.00 / night

(7)

1 / 50

Wailea House

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

$1,045.00

Excellent (7 reviews)

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from $1,045.00 / night

(15)

1 / 16

Wailea Apartment

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

$599.00

Very Good (15 reviews)

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from $599.00 / 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

(8)

1 / 50

Wailea Villa

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

$965.00

Excellent (8 reviews)

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from $965.00 / night

(2)

1 / 50

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

(2)

1 / 16

Wailea Apartment

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

$590.00

Excellent (2 reviews)

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from $590.00 / night

(1)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (1 reviews)

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from $1,395.00 / night

1 / 15

Wailea Apartment

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

$486.00

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from $486.00 / night

(7)

1 / 50

Wailea Villa

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

$995.00

Excellent (7 reviews)

Inquire

from $995.00 / 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

(2)

1 / 50

Wailea House

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

$1,045.00

Excellent (2 reviews)

Inquire

from $1,045.00 / night

(20)

1 / 16

Wailea Apartment

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

$496.00

Very Good (20 reviews)

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from $496.00 / night

(6)

1 / 50

Wailea Villa

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

$2,195.00

Excellent (6 reviews)

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from $2,195.00 / night

(7)

1 / 16

Wailea Apartment

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

$599.00

Very Good (7 reviews)

Inquire

from $599.00 / night

1 / 16

Wailea Apartment

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

$189.00

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from $189.00 / night

(9)

1 / 50

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

(5)

1 / 50

Wailea House

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

$1,295.00

Excellent (5 reviews)

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from $1,295.00 / night

(10)

1 / 50

Wailea Villa

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

$925.00

Excellent (10 reviews)

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from $925.00 / night

(11)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (11 reviews)

Inquire

from $1,495.00 / night

1 / 16

Wailea Apartment

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

$599.00

Inquire

from $599.00 / night

(13)

1 / 50

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

(1)

1 / 16

Wailea Apartment

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

$559.00

Excellent (1 reviews)

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from $559.00 / night