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Wailea 3-bedroom Vacation Rentals, Apartments & More - 84 Rentals Available.

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84 Vacation rentals

Filters applied: 3+ 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

(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

(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

(13)

1 / 16

Wailea Apartment

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

$229.00

Very Good (13 reviews)

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from $229.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • 5 nights min
  • 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. 48 minutes

$2,700.00

Very Good (2 reviews)

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from $2,700.00 / 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

(1)

1 / 50

Wailea House

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

$2,700.00

Excellent (1 reviews)

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from $2,700.00 / 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

(12)

1 / 16

Wailea Apartment

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

$1,499.00

Excellent (12 reviews)

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from $1,499.00 / night

(13)

1 / 50

Wailea House

  • 5
  • 10
  • 6 nights min
  • 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 / 16

Wailea Apartment

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

$499.00

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from $499.00 / night

(10)

1 / 50

Wailea Villa

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

$995.00

Excellent (10 reviews)

Inquire

from $995.00 / 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

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 / 16

Wailea Apartment

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

$800.00

Inquire

from $800.00 / night

(1)

1 / 15

Wailea Villa

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning

$1,595.00

Excellent (1 reviews)

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from $1,595.00 / 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

(4)

1 / 50

Wailea House

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

$1,450.00

Very Good (4 reviews)

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from $1,450.00 / night

(7)

1 / 50

Wailea House

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

$1,095.00

Excellent (7 reviews)

Inquire

from $1,095.00 / night

1 / 0

Wailea House

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

$2,095.00

Inquire

from $2,095.00 / night

(6)

1 / 50

Wailea House

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

$1,495.00

Excellent (6 reviews)

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from $1,495.00 / night

(7)

1 / 50

Wailea Villa

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

$1,145.00

Excellent (7 reviews)

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from $1,145.00 / night

(9)

1 / 50

Wailea Villa

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

$1,795.00

Excellent (9 reviews)

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from $1,795.00 / night

(2)

1 / 50

Wailea Villa

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

$1,045.00

Excellent (2 reviews)

Inquire

from $1,045.00 / night

(9)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (9 reviews)

Inquire

from $1,595.00 / 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

(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

(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

(5)

1 / 0

Wailea House

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

$1,495.00

Excellent (5 reviews)

Inquire

from $1,495.00 / night

(3)

1 / 50

Wailea Villa

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

$1,650.00

Very Good (3 reviews)

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from $1,650.00 / night

(11)

1 / 50

Wailea Villa

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

$1,695.00

Excellent (11 reviews)

Inquire

from $1,695.00 / night

(2)

1 / 50

Wailea House

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

$1,695.00

Very Good (2 reviews)

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from $1,695.00 / night

Your search has been expanded 14 miles to include more rentals

(9)

1 / 34

Kihei Townhouse - 5.4 miles away

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We enjoyed our stay in the KOA resort condo. The space was plenty for 4 adults and 3 kids and the proximity to the beach and other Maui activities was excellent. We weren't able to find some promised accessories in the condo and Kelli was very...”
- Review left on 11/27/2016

$430.00

Very Good (9 reviews)

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from $430.00 / night

(2)

1 / 19

Makawao House - 14 miles away

  • 4
  • 8
  • min stay varies

$295.00

Average (2 reviews)

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from $295.00 / 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

(2)

1 / 20

Kihei Townhouse - 5.4 miles away

  • 4
  • 10
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 47 minutes

“We really enjoyed our stay in the condo in Kihea.The accomodations were very comfortable and homey. We really appreciated the play equipment available for us to use, the coolers and all the kitchen equipment. The grounds were beatiful and well...”
- Review left on 04/25/2011

$516.00

Excellent (2 reviews)

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from $516.00 / 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

1 / 33

Kihei Townhouse - 4.8 miles away

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

$430.00

Book

from $430.00 / night