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Wailea 2-bedroom Vacation Rentals, Apartments & More - 227 Rentals Available.

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227 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 20

Wailea Condo

  • 2
  • 6
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$204.00

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from $204.00 / night

(101)

1 / 42

Wailea Villa

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

$1,140.00

Excellent (101 reviews)

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from $1,140.00 / night

(4)

1 / 16

Wailea Apartment

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

$763.00

Excellent (4 reviews)

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from $763.00 / night

(2)

1 / 50

Wailea House

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

$1,195.00

Excellent (2 reviews)

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from $1,195.00 / night

1 / 16

Wailea Apartment

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

$509.00

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from $509.00 / night

1 / 16

Wailea Apartment

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

$639.00

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from $639.00 / night

(7)

1 / 16

Wailea Apartment

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

$649.00

Very Good (7 reviews)

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from $649.00 / night

(1)

1 / 16

Wailea Apartment

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

$419.00

Excellent (1 reviews)

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from $419.00 / night

(7)

1 / 8

Wailea Apartment

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

$399.00

Excellent (7 reviews)

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from $399.00 / night

(1)

1 / 16

Wailea Apartment

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

$169.00

Excellent (1 reviews)

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from $169.00 / night

(1)

1 / 16

Wailea Apartment

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

$302.00

Excellent (1 reviews)

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from $302.00 / night

1 / 16

Wailea Apartment

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

$409.00

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from $409.00 / night

(1)

1 / 16

Wailea Apartment

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

$639.00

Excellent (1 reviews)

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from $639.00 / night

1 / 15

Wailea Apartment

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

$799.00

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from $799.00 / night

(1)

1 / 16

Wailea Apartment

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

$209.00

Excellent (1 reviews)

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from $209.00 / night

1 / 15

Wailea Apartment

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

$749.00

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from $749.00 / night

(21)

1 / 16

Wailea Apartment

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

$609.00

Very Good (21 reviews)

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from $609.00 / night

1 / 16

Wailea Apartment

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

$509.00

Inquire

from $509.00 / night

(13)

1 / 16

Wailea Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$249.00

Very Good (13 reviews)

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from $249.00 / night

1 / 16

Wailea Apartment

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

$809.00

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from $809.00 / night

(17)

1 / 9

Wailea Apartment

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

$399.00

Inquire

from $399.00 / night

1 / 15

Wailea Condo

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

$295.00

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from $295.00 / night

(8)

1 / 10

Wailea Apartment

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

$690.00

Very Good (8 reviews)

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from $690.00 / night

(7)

1 / 16

Wailea Apartment

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

$399.00

Excellent (7 reviews)

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from $399.00 / night

(1)

1 / 16

Wailea Apartment

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

$899.00

Excellent (1 reviews)

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from $899.00 / night

1 / 16

Wailea Apartment

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

$409.00

Inquire

from $409.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$299.00

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from $299.00 / 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

(9)

1 / 16

Wailea Apartment

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

$409.00

Very Good (9 reviews)

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from $409.00 / night

(1)

1 / 16

Wailea Apartment

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

$1,459.00

Excellent (1 reviews)

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from $1,459.00 / night

(11)

1 / 16

Wailea Apartment

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

$739.00

Very Good (11 reviews)

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from $739.00 / night

(2)

1 / 16

Wailea Apartment

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

$639.00

Excellent (2 reviews)

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from $639.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$1,421.00

Excellent (12 reviews)

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from $1,421.00 / night

(1)

1 / 50

Wailea House

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

$2,900.00

Excellent (1 reviews)

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from $2,900.00 / night

(1)

1 / 50

Wailea House

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

$1,525.00

Excellent (1 reviews)

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from $1,525.00 / night

1 / 50

Wailea House

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

$2,850.00

Inquire

from $2,850.00 / night

(16)

1 / 16

Wailea Apartment

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

$409.00

Excellent (16 reviews)

Inquire

from $409.00 / night

1 / 15

Wailea Apartment

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

$679.00

Inquire

from $679.00 / night

(8)

1 / 16

Wailea Apartment

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

$649.00

Very Good (8 reviews)

Inquire

from $649.00 / night