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Wailea 3-bedroom Vacation Rentals, Apartments & More - 54 Rentals Available.

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54 Vacation rentals

Filters applied: 3+ Bedrooms

1 / 24

Wailea House

  • 5
  • 8
  • 6 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$2,165.00

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from $2,165.00 / night

(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

$1,195.00

Excellent (2 reviews)

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from $1,195.00 / 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

  • 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

$2,850.00

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from $2,850.00 / night

(13)

1 / 50

Wailea House

  • 5
  • 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,950.00

Very Good (13 reviews)

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from $2,950.00 / night

(1)

1 / 50

Wailea House

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

$2,900.00

Excellent (1 reviews)

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from $2,900.00 / 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

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

(6)

1 / 50

Wailea Villa

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

$2,145.00

Excellent (6 reviews)

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from $2,145.00 / night

(10)

1 / 50

Wailea Villa

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

$995.00

Excellent (10 reviews)

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from $995.00 / night

(9)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (9 reviews)

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from $1,595.00 / night

(6)

1 / 50

Wailea House

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

$1,695.00

Excellent (6 reviews)

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from $1,695.00 / 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

(1)

1 / 50

Wailea Villa

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

$1,250.00

Excellent (1 reviews)

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from $1,250.00 / night

(9)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (9 reviews)

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from $1,495.00 / night

(2)

1 / 50

Wailea Villa

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

$995.00

Excellent (2 reviews)

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from $995.00 / night

(7)

1 / 50

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

(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
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,595.00

Excellent (1 reviews)

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from $1,595.00 / night

(3)

1 / 50

Wailea Villa

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

$1,595.00

Very Good (3 reviews)

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from $1,595.00 / night

(2)

1 / 50

Wailea House

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

$2,095.00

Very Good (2 reviews)

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from $2,095.00 / night

(11)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (11 reviews)

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from $1,395.00 / night

Your search has been expanded 18.9 miles to include more rentals

(7)

1 / 26

Kihei House - 3.2 miles away

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

Responds fast! Avg. 2 hours 58 minutes

“Don't even bother looking at any other properties, this one is your home away from home. We had a large group, seven adults and my one year old daughter. This place was perfect. We all were comfortable and felt right at home. Everything was there and...”
- Review left on 06/28/2016

$602.00

Very Good (7 reviews)

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from $602.00 / night

(2)

1 / 20

Kihei Townhouse - 5.4 miles away

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

Responds fast! Avg. 2 hours 58 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

(87)

1 / 17

Haiku House - 18 miles away

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

Responds fast! Avg. 2 hours 55 minutes

“My husband and I looked at several houses on Maui but Hale Mauka Makai was the only one that truly caught our eye. For 11 days it was our own private paradise on Maui. We knew we wanted to stay someplace on north Maui, away from the resort towns and...”
- Review left on 10/29/2017

$802.00

Excellent (87 reviews)

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from $802.00 / night

(37)

1 / 24

Kihei House - 1.6 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly

Responds fast! Avg. 53 minutes

$916.00

Excellent (37 reviews)

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from $916.00 / 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
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

$259.00

Very Good (3 reviews)

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from $259.00 / night

(2)

1 / 19

Makawao House - 14 miles away

  • 4
  • 8
  • 4 nights min

$295.00

Average (2 reviews)

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from $295.00 / night

(1)

1 / 34

Kihei Condo - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$872.00

Excellent (1 reviews)

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from $872.00 / night

(1)

1 / 19

Kihei House - 1.3 miles away

  • 4
  • 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This split-level hillside home has stunning views, an orchard, pool and kitchen garden. The caretaker provided baskets of citrus fruit from the orchard (sweetest grapefruit ever) and invited us to make use of the kitchen garden. I harvested a beet...”
- Review left on 01/03/2017

$1,802.00

Very Good (1 reviews)

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from $1,802.00 / night

(1)

1 / 10

Makawao House - 14 miles away

  • 3
  • 6
  • 4 nights min

$295.00

Excellent (1 reviews)

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from $295.00 / night

(8)

1 / 73

Lahaina Apartment - 18.9 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$421.00

Very Good (8 reviews)

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from $421.00 / night

(2)

1 / 50

Kihei House - 4.1 miles away

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

$1,495.00

Excellent (2 reviews)

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from $1,495.00 / night

(12)

1 / 50

Kihei House - 4.1 miles away

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

$1,896.00

Excellent (12 reviews)

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from $1,896.00 / night

(2)

1 / 50

Kihei House - 4.1 miles away

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

$2,600.00

Average (2 reviews)

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from $2,600.00 / night

1 / 50

Kihei Villa - 0.1 miles away

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

$2,825.00

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from $2,825.00 / night

1 / 50

Kihei Villa - 0.1 miles away

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

$1,095.00

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from $1,095.00 / night