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Wailea 3-bedroom Vacation Rentals, Apartments & More - 101 Rentals Available.

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101 Vacation rentals

Filters applied: 3+ Bedrooms

1 / 24

Wailea House

  • 5
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,632.00

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from $1,632.00 / 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

(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

(13)

1 / 16

Wailea Apartment

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

$250.00

Very Good (13 reviews)

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from $250.00 / night

1 / 16

Wailea Apartment

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

$265.00

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from $265.00 / night

(2)

1 / 24

Wailea Villa

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

Responds fast! Avg. 1 hour 15 minutes

$2,700.00

Very Good (2 reviews)

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from $2,700.00 / night

(12)

1 / 16

Wailea Apartment

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

$1,475.00

Excellent (12 reviews)

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from $1,475.00 / night

(1)

1 / 16

Wailea Apartment

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

$1,295.00

Excellent (1 reviews)

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from $1,295.00 / night

(8)

1 / 50

Wailea Villa

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

$1,095.00

Excellent (8 reviews)

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from $1,095.00 / night

(13)

1 / 50

Wailea House

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

$3,050.00

Very Good (13 reviews)

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from $3,050.00 / night

(1)

1 / 50

Wailea House

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

$1,695.00

Excellent (1 reviews)

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from $1,695.00 / night

1 / 50

Wailea House

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

$2,750.00

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from $2,750.00 / night

(10)

1 / 50

Wailea Villa

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

$850.00

Excellent (10 reviews)

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from $850.00 / night

(6)

1 / 50

Wailea Villa

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

$2,195.00

Excellent (6 reviews)

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from $2,195.00 / night

1 / 16

Wailea Apartment

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

$525.00

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from $525.00 / night

(4)

1 / 50

Wailea House

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

$1,250.00

Very Good (4 reviews)

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from $1,250.00 / night

(1)

1 / 50

Wailea House

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

$2,700.00

Excellent (1 reviews)

Inquire

from $2,700.00 / night

1 / 50

Wailea House

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

$1,095.00

Inquire

from $1,095.00 / night

1 / 0

Wailea House

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

$1,995.00

Inquire

from $1,995.00 / night

1 / 16

Wailea Apartment

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

$800.00

Inquire

from $800.00 / night

(7)

1 / 50

Wailea House

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

$1,095.00

Excellent (7 reviews)

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from $1,095.00 / night

(6)

1 / 50

Wailea House

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

$1,395.00

Excellent (6 reviews)

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from $1,395.00 / night

(1)

1 / 15

Wailea Villa

  • 3
  • 6
  • 5 nights min
  • Ask about children
  • Air conditioning

$2,295.00

Excellent (1 reviews)

Inquire

from $2,295.00 / night

(9)

1 / 50

Wailea Villa

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

$1,695.00

Excellent (9 reviews)

Inquire

from $1,695.00 / night

(9)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (9 reviews)

Inquire

from $1,395.00 / night

(7)

1 / 50

Wailea Villa

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

$1,095.00

Excellent (7 reviews)

Inquire

from $1,095.00 / night

(1)

1 / 50

Wailea Villa

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

$1,295.00

Excellent (1 reviews)

Inquire

from $1,295.00 / night

(5)

1 / 0

Wailea House

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

$1,195.00

Excellent (5 reviews)

Inquire

from $1,195.00 / night

(2)

1 / 50

Wailea Villa

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

$1,195.00

Excellent (2 reviews)

Inquire

from $1,195.00 / night

(2)

1 / 50

Wailea Villa

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

$1,045.00

Excellent (2 reviews)

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from $1,045.00 / night

(1)

1 / 50

Wailea Villa

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

$1,450.00

Excellent (1 reviews)

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from $1,450.00 / night

(3)

1 / 50

Wailea Villa

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

$1,495.00

Very Good (3 reviews)

Inquire

from $1,495.00 / night

(11)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (11 reviews)

Inquire

from $1,495.00 / night

(2)

1 / 50

Wailea House

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

$1,695.00

Very Good (2 reviews)

Inquire

from $1,695.00 / night

Your search has been expanded 6.8 miles to include more rentals

(5)

1 / 20

Kihei House - 6.8 miles away

  • 4
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 28 minutes

“Rented for two weeks with my four grand children and thier parents. very clean well kept and well equiped, very nice pool and deck area, across a QUITE street to a nice beach for the kids to play all in, walking distance to good resturants, groceries...”
- Review left on 03/28/2013

$459.00

Excellent (5 reviews)

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from $459.00 / night

(18)

1 / 40

Kihei House - 4.8 miles away

  • 6
  • 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This is a great place to stay when visiting Maui for a family vacation. The home is located on a quiet street near roads that provide for easy access to major tourist sites on the island and is near some great beaches. The town of Kihie has all...”
- Review left on 10/13/2014

$716.00

Very Good (18 reviews)

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from $716.00 / night

1 / 45

Kihei Townhouse - 5.4 miles away

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

$430.00

Book

from $430.00 / night

1 / 20

Kihei Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$1,149.00

Book

from $1,149.00 / night

1 / 11

Kihei Villa - 0.1 miles away

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$1,149.00

Book

from $1,149.00 / night

1 / 39

Kihei Villa - 0.1 miles away

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$2,950.00

Book

from $2,950.00 / night