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Wailea Vacation Rentals & Apartments - 507 Rentals Available

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507 Vacation rentals

(1)

1 / 10

Wailea Apartment

  • 1
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$185.00

Excellent (1 reviews)

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from $185.00 / 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

(101)

1 / 42

Wailea Villa

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

$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
  • Ski
  • Child friendly

$762.00

Excellent (4 reviews)

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from $762.00 / night

(13)

1 / 0

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

(2)

1 / 50

Wailea House

  • 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

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$235.00

Very Good (2 reviews)

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from $235.00 / 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

(5)

1 / 16

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$299.00

Excellent (5 reviews)

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from $299.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$440.00

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from $440.00 / night

(7)

1 / 8

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$425.00

Excellent (7 reviews)

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from $425.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$612.00

Very Good (7 reviews)

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from $612.00 / night

1 / 15

Wailea Apartment

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

$762.00

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from $762.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$599.00

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from $599.00 / night

1 / 15

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$699.00

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from $699.00 / night

(13)

1 / 16

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$165.00

Average (13 reviews)

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from $165.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$292.00

Excellent (1 reviews)

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from $292.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$440.00

Inquire

from $440.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$419.00

Inquire

from $419.00 / night

(20)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$495.00

Very Good (20 reviews)

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from $495.00 / night

1 / 16

Wailea Apartment

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

$380.00

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from $380.00 / night

(17)

1 / 7

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$421.00

Very Good (17 reviews)

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from $421.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$200.00

Inquire

from $200.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$409.00

Inquire

from $409.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$590.00

Inquire

from $590.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$899.00

Inquire

from $899.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$699.00

Inquire

from $699.00 / night

(17)

1 / 9

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$409.00

Excellent (17 reviews)

Inquire

from $409.00 / 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

(13)

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$250.00

Very Good (13 reviews)

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from $250.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$409.00

Excellent (7 reviews)

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from $409.00 / night

(2)

1 / 24

Wailea Villa

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

Responds fast! Avg. 11 minutes

$2,700.00

Very Good (2 reviews)

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from $2,700.00 / night

(2)

1 / 16

Wailea Apartment

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$590.00

Excellent (2 reviews)

Inquire

from $590.00 / night

(16)

1 / 16

Wailea Apartment

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$399.00

Very Good (16 reviews)

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from $399.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$265.00

Inquire

from $265.00 / night

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$409.00

Inquire

from $409.00 / night

(8)

1 / 50

Wailea Villa

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

$945.00

Excellent (8 reviews)

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from $945.00 / night

(9)

1 / 16

Wailea Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$409.00

Very Good (9 reviews)

Inquire

from $409.00 / night

(12)

1 / 16

Wailea Apartment

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$1,570.00

Excellent (12 reviews)

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from $1,570.00 / night

1 / 5

Wailea Apartment

  • 1
  • 2
  • 5 nights min
  • Swimming pool
  • Ski
  • Child friendly

$399.00

Inquire

from $399.00 / night