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Wailea Vacation Rentals & Apartments - 95 Rentals Available

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95 Vacation rentals

(96)

1 / 42

Wailea Villa

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

$895

Excellent (96 reviews)

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from $895 / night

(7)

1 / 37

Wailea Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$1288

Excellent (7 reviews)

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from $1288 / night

(9)

1 / 25

Wailea Condo

  • 2
  • 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$280

Very Good (9 reviews)

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from $280 / night

(4)

1 / 16

Wailea Apartment

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

$383

Very Good (4 reviews)

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from $383 / night

(16)

1 / 16

Wailea Apartment

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

$383

Excellent (16 reviews)

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from $383 / night

1 / 16

Wailea Apartment

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

from $267 / night

(2)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children

$293

Very Good (2 reviews)

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from $293 / night

1 / 20

Wailea Apartment

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

from $305 / night

(7)

1 / 16

Wailea Apartment

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

$425

Excellent (7 reviews)

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from $425 / night

(7)

1 / 16

Wailea Apartment

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

$499

Very Good (7 reviews)

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from $499 / night

(16)

1 / 16

Wailea Apartment

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

$540

Excellent (16 reviews)

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from $540 / night

(1)

1 / 16

Wailea Apartment

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

$446

Excellent (1 reviews)

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from $446 / night

1 / 25

Wailea Apartment

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

from $335 / night

1 / 16

Wailea Apartment

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

from $339 / night

(4)

1 / 19

Wailea Apartment

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

$345

Excellent (4 reviews)

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from $345 / night

(4)

1 / 24

Wailea Apartment

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

$690

Excellent (4 reviews)

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from $690 / night

(12)

1 / 16

Wailea Apartment

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

$1166

Excellent (12 reviews)

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from $1166 / night

(1)

1 / 22

Wailea Apartment

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

$250

Very Good (1 reviews)

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from $250 / night

(4)

1 / 16

Wailea Apartment

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

$599

Excellent (4 reviews)

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from $599 / night

(4)

1 / 16

Wailea Apartment

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

$612

Excellent (4 reviews)

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from $612 / night

(2)

1 / 13

Wailea Apartment

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

$225

Very Good (2 reviews)

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from $225 / night

(16)

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children

$375

Very Good (16 reviews)

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from $375 / night

1 / 16

Wailea Apartment

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

from $519 / night

(7)

1 / 16

Wailea Apartment

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

$519

Very Good (7 reviews)

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from $519 / night

(1)

1 / 16

Wailea Apartment

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

$599

Excellent (1 reviews)

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from $599 / 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

(11)

1 / 16

Wailea Apartment

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

$599

Very Good (11 reviews)

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from $599 / night

1 / 19

Wailea Apartment

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

from $270 / night

(20)

1 / 16

Wailea Apartment

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

$446

Very Good (20 reviews)

Inquire

from $446 / night

1 / 16

Wailea Apartment

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

from $440 / night

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Ask about children

from $293 / night

(6)

1 / 16

Wailea Apartment

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

$383

Excellent (6 reviews)

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from $383 / night

1 / 13

Wailea Apartment

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

from $215 / night

1 / 22

Wailea House

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Ask about pets

from $244 / night

1 / 16

Wailea Apartment

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

from $440 / night

1 / 16

Wailea Apartment

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

from $383 / night

1 / 16

Wailea Apartment

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

from $675 / night

(2)

1 / 19

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

(2)

1 / 18

Wailea Apartment

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

$410

Excellent (2 reviews)

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from $410 / night

(3)

1 / 17

Wailea Apartment

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

$260

Excellent (3 reviews)

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from $260 / night