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Wailea 2-bedroom Vacation Rentals, Apartments & More - 253 Rentals Available.

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253 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 24

Wailea House

  • 5
  • 11
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$1,632.00

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from $1,632.00 / night

1 / 20

Wailea Condo

  • 2
  • 6
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 12 minutes

$183.00

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from $183.00 / night

(101)

1 / 42

Wailea Villa

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

Responds fast! Avg. 1 hour 43 minutes

$995.00

Excellent (101 reviews)

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from $995.00 / night

(4)

1 / 16

Wailea Apartment

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

$689.00

Excellent (4 reviews)

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from $689.00 / night

(13)

1 / 0

Wailea House

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$926.00

Excellent (13 reviews)

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from $926.00 / night

(2)

1 / 50

Wailea House

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

$1,145.00

Excellent (2 reviews)

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from $1,145.00 / night

(7)

1 / 16

Wailea Apartment

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

$612.00

Very Good (7 reviews)

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from $612.00 / night

1 / 16

Wailea Apartment

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

$440.00

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from $440.00 / night

(7)

1 / 8

Wailea Apartment

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

$379.00

Excellent (7 reviews)

Inquire

from $379.00 / night

1 / 15

Wailea Apartment

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

$689.00

Inquire

from $689.00 / night

1 / 16

Wailea Apartment

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

$649.00

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from $649.00 / 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
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$269.00

Excellent (1 reviews)

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from $269.00 / night

1 / 16

Wailea Apartment

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

$189.00

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from $189.00 / night

1 / 15

Wailea Apartment

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

$749.00

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from $749.00 / 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 / 16

Wailea Apartment

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

$379.00

Inquire

from $379.00 / night

(13)

1 / 16

Wailea Apartment

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

$229.00

Very Good (13 reviews)

Inquire

from $229.00 / night

1 / 34

Wailea Condo

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

$295.00

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from $295.00 / night

(20)

1 / 16

Wailea Apartment

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

$449.00

Very Good (20 reviews)

Inquire

from $449.00 / night

1 / 16

Wailea Apartment

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

$599.00

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from $599.00 / night

(2)

1 / 24

Wailea Villa

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$2,701.00

Very Good (2 reviews)

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from $2,701.00 / night

(17)

1 / 9

Wailea Apartment

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

$409.00

Excellent (17 reviews)

Inquire

from $409.00 / night

1 / 16

Wailea Apartment

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

$399.00

Inquire

from $399.00 / night

1 / 16

Wailea Apartment

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

$389.00

Inquire

from $389.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$265.00

Inquire

from $265.00 / night

1 / 16

Wailea Apartment

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

$409.00

Inquire

from $409.00 / night

(7)

1 / 16

Wailea Apartment

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

$409.00

Excellent (7 reviews)

Inquire

from $409.00 / night

(9)

1 / 16

Wailea Apartment

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

$399.00

Very Good (9 reviews)

Inquire

from $399.00 / night

1 / 16

Wailea Apartment

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

$829.00

Inquire

from $829.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$1,499.00

Excellent (12 reviews)

Inquire

from $1,499.00 / night

1 / 16

Wailea Apartment

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

$899.00

Inquire

from $899.00 / night

(8)

1 / 50

Wailea Villa

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

$995.00

Excellent (8 reviews)

Inquire

from $995.00 / night

(1)

1 / 16

Wailea Apartment

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

$629.00

Excellent (1 reviews)

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from $629.00 / night

(1)

1 / 16

Wailea Apartment

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

$1,299.00

Excellent (1 reviews)

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from $1,299.00 / night

(8)

1 / 10

Wailea Apartment

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

$649.00

Very Good (8 reviews)

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from $649.00 / night

1 / 50

Wailea House

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

$2,750.00

Inquire

from $2,750.00 / night

(7)

1 / 16

Wailea Apartment

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

$689.00

Very Good (7 reviews)

Inquire

from $689.00 / 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)

1 / 50

Wailea House

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

$2,701.00

Excellent (1 reviews)

Inquire

from $2,701.00 / night