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Wailea 2-bedroom Vacation Rentals, Apartments & More - 110 Rentals Available.

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110 Vacation rentals

Filters applied: 2+ 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

1 / 20

Wailea Condo

  • 2
  • 6
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$204.00

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from $204.00 / 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

1 / 15

Wailea Condo

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$295.00

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from $295.00 / 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

1 / 33

Wailea Condo

  • 2
  • 6
  • 5 nights min
  • Child friendly

$179.00

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from $179.00 / 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

1 / 42

Wailea Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$295.00

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from $295.00 / 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 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

(1)

1 / 23

Kihei Condo - 0.1 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“Condo was a 2 bedroom, 2bathroom with a nice size outside lanai with a bbq. Good location and handy to Wailea and Kihei. Pool was very nice and everything in the condo was good but maybe a bit dated decor wise but more than adequate. The complex is...”
- Review left on 10/12/2016

$361.00

Very Good (1 reviews)

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from $361.00 / night

(7)

1 / 42

Kihei Condo - 6.8 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“We had a great time at this place, the view is amazing, confortable , clean with everything we need... Hope to get there another time”
- Review left on 08/16/2016

$338.00

Excellent (7 reviews)

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from $338.00 / night

(1)

1 / 21

Kihei Condo - 2.3 miles away

  • 2
  • 5
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Very nice stay at this condo in Maui. The place was beautiful and had a great view. Easy walk to the beach was a plus. Unit was very clean and we really enjoyed staying. Can't wait to come back...”
- Review left on 02/25/2016

$224.00

Excellent (1 reviews)

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from $224.00 / night

1 / 27

Kihei Condo - 1.6 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$320.00

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from $320.00 / 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

1 / 85

Kihei Condo - 2.7 miles away

  • 2
  • 6
  • 4 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Ask about children

Responds fast! Avg. 1 hour 36 minutes

$458.00

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from $458.00 / 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

1 / 19

Kihei Condo - 1.9 miles away

  • 2
  • 6
  • 5 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$229.00

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from $229.00 / night

(1)

1 / 28

Kihei Condo - 5.2 miles away

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$250.00

Excellent (1 reviews)

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from $250.00 / 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