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Wailea 3-bedroom Vacation Rentals, Apartments & More - 44 Rentals Available.

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44 Vacation rentals

Filters applied: 3+ Bedrooms

(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

(2)

1 / 50

Wailea House

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

$1,295.00

Excellent (2 reviews)

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from $1,295.00 / night

(13)

1 / 24

Wailea Apartment

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

$275.00

Very Good (13 reviews)

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from $275.00 / 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

(13)

1 / 30

Wailea Apartment

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

$1,570.00

Excellent (13 reviews)

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from $1,570.00 / night

(1)

1 / 50

Wailea House

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

$3,001.00

Excellent (1 reviews)

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from $3,001.00 / night

(1)

1 / 50

Wailea House

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

$1,950.00

Excellent (1 reviews)

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from $1,950.00 / night

1 / 50

Wailea House

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

$2,795.00

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from $2,795.00 / night

(4)

1 / 50

Wailea House

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

$1,375.00

Very Good (4 reviews)

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from $1,375.00 / night

1 / 24

Wailea Apartment

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

$439.00

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from $439.00 / night

1 / 50

Wailea House

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

$1,195.00

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from $1,195.00 / night

(13)

1 / 50

Wailea House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,995.00

Very Good (13 reviews)

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from $3,995.00 / night

(10)

1 / 50

Wailea Villa

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

$1,050.00

Excellent (10 reviews)

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from $1,050.00 / night

1 / 24

Wailea Apartment

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

$899.00

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from $899.00 / night

(6)

1 / 50

Wailea Villa

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

$2,595.00

Excellent (6 reviews)

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from $2,595.00 / night

(6)

1 / 50

Wailea House

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,775.00

Excellent (6 reviews)

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from $1,775.00 / night

(7)

1 / 50

Wailea House

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

$1,195.00

Excellent (7 reviews)

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from $1,195.00 / night

(7)

1 / 49

Wailea Villa

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

$995.00

Excellent (7 reviews)

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from $995.00 / night

(9)

1 / 50

Wailea Villa

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

$1,775.00

Excellent (9 reviews)

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from $1,775.00 / night

(9)

1 / 50

Wailea Villa

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

$1,466.00

Excellent (9 reviews)

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from $1,466.00 / night

(1)

1 / 50

Wailea Villa

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

$1,375.00

Excellent (1 reviews)

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from $1,375.00 / night

(2)

1 / 50

Wailea Villa

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

$1,150.00

Excellent (2 reviews)

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from $1,150.00 / night

(1)

1 / 50

Wailea Villa

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

$1,295.00

Excellent (1 reviews)

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from $1,295.00 / night

(2)

1 / 50

Wailea Villa

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

$1,245.00

Excellent (2 reviews)

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from $1,245.00 / night

(3)

1 / 50

Wailea Villa

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

$1,950.00

Very Good (3 reviews)

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from $1,950.00 / night

(11)

1 / 50

Wailea Villa

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,625.00

Excellent (11 reviews)

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from $1,625.00 / night

(2)

1 / 50

Wailea House

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

$2,250.00

Very Good (2 reviews)

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from $2,250.00 / night

1 / 47

Wailea House

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

$2,595.00

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from $2,595.00 / night

Your search has been expanded 18 miles to include more rentals

(4)

1 / 24

Kihei Apartment - 2.3 miles away

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

$459.00

Average (4 reviews)

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from $459.00 / night

(87)

1 / 17

Haiku House - 18 miles away

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

$802.00

Excellent (87 reviews)

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from $802.00 / night

(18)

1 / 24

Kihei Apartment - 5.4 miles away

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

$514.00

Very Good (18 reviews)

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from $514.00 / night

(3)

1 / 24

Kihei Apartment - 2.3 miles away

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

$619.00

Very Good (3 reviews)

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from $619.00 / night

(5)

1 / 18

Kihei Apartment - 5.4 miles away

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

$245.00

Very Good (5 reviews)

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from $245.00 / night

(3)

1 / 37

Kula House - 10.3 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

$259.00

Very Good (3 reviews)

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from $259.00 / night

(14)

1 / 24

Kihei Apartment - 5.4 miles away

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

$435.00

Very Good (14 reviews)

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from $435.00 / night

(22)

1 / 24

Kihei Apartment - 2.3 miles away

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

$519.00

Very Good (22 reviews)

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from $519.00 / night

1 / 50

Kihei Villa - 0.1 miles away

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

$1,150.00

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from $1,150.00 / night

1 / 24

Kihei Apartment - 2.3 miles away

  • 3
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$439.00

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from $439.00 / night

(1)

1 / 32

Kihei Condo - 0.1 miles away

  • 3
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$881.00

Excellent (1 reviews)

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from $881.00 / night

(5)

1 / 24

Kihei Apartment - 2.3 miles away

  • 3
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$459.00

Very Good (5 reviews)

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from $459.00 / night