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Wailea Vacation Rentals & Apartments with Swimming Pool - 68 Rentals Available.

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68 Vacation rentals

Filters applied: Swimming pool

(97)

1 / 42

Wailea Villa

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

$895

Excellent (97 reviews)

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from $895 / night

(16)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$540

Excellent (16 reviews)

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from $540 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $599 / night

(20)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$446

Very Good (20 reviews)

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from $446 / night

(1)

1 / 23

Wailea Condo

  • 1
  • 4
  • 4 nights min
  • Swimming pool
  • Air conditioning

$199

Excellent (1 reviews)

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from $199 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$612

Excellent (4 reviews)

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from $612 / night

(8)

1 / 19

Wailea Apartment

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$810

Excellent (8 reviews)

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from $810 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$599

Excellent (1 reviews)

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from $599 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$579

Very Good (7 reviews)

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from $579 / night

1 / 25

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $315 / night

(3)

1 / 19

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$230

Very Good (3 reviews)

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from $230 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $540 / night

1 / 16

Wailea Apartment

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

from $267 / night

(1)

1 / 22

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$225

Very Good (1 reviews)

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from $225 / night

1 / 20

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $265 / night

(2)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$540

Excellent (2 reviews)

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from $540 / night

(2)

1 / 19

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$235

Very Good (2 reviews)

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from $235 / night

(3)

1 / 18

Wailea Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$220

Very Good (3 reviews)

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from $220 / night

(3)

1 / 21

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$385

Excellent (3 reviews)

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from $385 / night

(18)

1 / 14

Wailea Apartment

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

$220

Very Good (18 reviews)

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from $220 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$700

Excellent (1 reviews)

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from $700 / night

(13)

1 / 17

Wailea Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$235

Excellent (13 reviews)

Inquire

from $235 / night

(10)

1 / 16

Wailea Apartment

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

$250

Very Good (10 reviews)

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from $250 / night

1 / 20

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $270 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$612

Very Good (7 reviews)

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from $612 / night

(14)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$612

Very Good (14 reviews)

Inquire

from $612 / night

(8)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$540

Very Good (8 reviews)

Inquire

from $540 / night

(5)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$540

Very Good (5 reviews)

Inquire

from $540 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$612

Very Good (7 reviews)

Inquire

from $612 / night

(2)

1 / 20

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$325

Very Good (2 reviews)

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from $325 / night

(1)

1 / 19

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$370

Average (1 reviews)

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from $370 / night

(2)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$473

Very Good (2 reviews)

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from $473 / night

(3)

1 / 17

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$235

Excellent (3 reviews)

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from $235 / night

(3)

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$680

Very Good (3 reviews)

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from $680 / night

(2)

1 / 20

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$260

Very Good (2 reviews)

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from $260 / night

1 / 13

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $200 / night

(2)

1 / 13

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$210

Very Good (2 reviews)

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from $210 / night

1 / 27

Wailea Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $435 / night

(4)

1 / 19

Wailea Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$325

Excellent (4 reviews)

Inquire

from $325 / night

(13)

1 / 16

Wailea Apartment

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

$250

Very Good (13 reviews)

Inquire

from $250 / night