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Wailea 3-bedroom Vacation Rentals, Apartments & More - 58 Rentals Available.

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58 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

$1,395.00

Excellent (2 reviews)

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from $1,395.00 / night

(13)

1 / 24

Wailea Apartment

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

$220.00

Very Good (13 reviews)

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from $220.00 / night

(8)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (8 reviews)

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from $1,395.00 / night

(12)

1 / 30

Wailea Apartment

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

$1,421.00

Excellent (12 reviews)

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from $1,421.00 / night

(1)

1 / 50

Wailea House

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

$2,901.00

Excellent (1 reviews)

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from $2,901.00 / night

(1)

1 / 50

Wailea House

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

$1,595.00

Excellent (1 reviews)

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from $1,595.00 / night

1 / 50

Wailea House

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

$2,851.00

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from $2,851.00 / night

(4)

1 / 50

Wailea House

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

$1,495.00

Very Good (4 reviews)

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from $1,495.00 / night

1 / 24

Wailea Apartment

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

$419.00

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from $419.00 / night

1 / 50

Wailea House

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

$1,595.00

Inquire

from $1,595.00 / night

(13)

1 / 50

Wailea House

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

$2,951.00

Very Good (13 reviews)

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from $2,951.00 / night

(10)

1 / 50

Wailea Villa

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

$1,045.00

Excellent (10 reviews)

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from $1,045.00 / night

1 / 24

Wailea Apartment

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

$799.00

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from $799.00 / night

(6)

1 / 50

Wailea Villa

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

$2,295.00

Excellent (6 reviews)

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from $2,295.00 / night

(6)

1 / 50

Wailea House

  • 4
  • 8
  • 5 nights min
  • 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

$1,495.00

Excellent (7 reviews)

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from $1,495.00 / night

(7)

1 / 0

Wailea Villa

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

$1,495.00

Excellent (7 reviews)

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from $1,495.00 / night

(9)

1 / 50

Wailea Villa

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

$1,695.00

Excellent (9 reviews)

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from $1,695.00 / night

(9)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (9 reviews)

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from $1,495.00 / night

(1)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (1 reviews)

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from $1,395.00 / night

(2)

1 / 50

Wailea Villa

  • 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)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (1 reviews)

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from $1,495.00 / night

(2)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (2 reviews)

Inquire

from $1,395.00 / night

(3)

1 / 50

Wailea Villa

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

$1,695.00

Very Good (3 reviews)

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from $1,695.00 / night

(11)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (11 reviews)

Inquire

from $1,595.00 / night

(2)

1 / 50

Wailea House

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

$2,395.00

Very Good (2 reviews)

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from $2,395.00 / night

Your search has been expanded 18 miles to include more rentals

(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

(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

(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

(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

(87)

1 / 17

Haiku House - 18 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
“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. 32 minutes

$916.00

Excellent (37 reviews)

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from $916.00 / night

(18)

1 / 24

Kihei Apartment - 5.4 miles away

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

$409.00

Very Good (18 reviews)

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from $409.00 / night

(4)

1 / 24

Kihei Apartment - 2.3 miles away

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

$419.00

Average (4 reviews)

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from $419.00 / night

(21)

1 / 24

Kihei Apartment - 2.3 miles away

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

$439.00

Very Good (21 reviews)

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from $439.00 / night

(4)

1 / 24

Kihei Apartment - 2.3 miles away

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

$419.00

Very Good (4 reviews)

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from $419.00 / night

(14)

1 / 24

Kihei Apartment - 5.4 miles away

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

$349.00

Very Good (14 reviews)

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from $349.00 / night

(2)

1 / 24

Kihei Apartment - 2.3 miles away

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

$549.00

Very Good (2 reviews)

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from $549.00 / 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