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Wailea 3-bedroom Vacation Rentals, Apartments & More - 68 Rentals Available.

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68 Vacation rentals

Filters applied: 3+ Bedrooms

1 / 24

Wailea House

  • 5
  • 8
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$2,163.00

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from $2,163.00 / 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

$1,140.00

Excellent (101 reviews)

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from $1,140.00 / night

(2)

1 / 50

Wailea House

  • 3
  • 6
  • min stay varies
  • 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

$239.00

Very Good (13 reviews)

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from $239.00 / 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

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

(1)

1 / 50

Wailea House

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

$1,895.00

Excellent (1 reviews)

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from $1,895.00 / 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 / 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

(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

(10)

1 / 50

Wailea Villa

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

$995.00

Excellent (10 reviews)

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from $995.00 / 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

(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

(4)

1 / 50

Wailea House

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

$1,395.00

Very Good (4 reviews)

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from $1,395.00 / night

1 / 0

Wailea House

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

$2,295.00

Inquire

from $2,295.00 / night

1 / 16

Wailea Apartment

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

$459.00

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from $459.00 / night

1 / 16

Wailea Apartment

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

$800.00

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from $800.00 / night

1 / 50

Wailea House

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

$1,095.00

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from $1,095.00 / night

(6)

1 / 50

Wailea House

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

$1,895.00

Excellent (6 reviews)

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from $1,895.00 / 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

(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

(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

(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

$995.00

Excellent (2 reviews)

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from $995.00 / night

(9)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (9 reviews)

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from $1,595.00 / night

(5)

1 / 0

Wailea House

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

$1,495.00

Excellent (5 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

(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

(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

(2)

1 / 50

Wailea Villa

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

$1,195.00

Excellent (2 reviews)

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from $1,195.00 / 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)

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from $1,695.00 / night

(2)

1 / 0

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 18 miles to include more rentals

(86)

1 / 16

Haiku House - 18 miles away

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

Responds fast! Avg. 3 hours 2 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

$687.00

Excellent (86 reviews)

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from $687.00 / 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 47 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

(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

1 / 16

Kihei Apartment - 2.3 miles away

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

$459.00

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from $459.00 / night

(2)

1 / 16

Kihei Apartment - 2.3 miles away

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

$539.00

Very Good (2 reviews)

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from $539.00 / 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

(2)

1 / 37

Kihei Condo - 5.4 miles away

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We very much enjoyed our stay in Unit 4G. The condo is nicely furnished and very roomy & comfortable. I plan on renting this unit for another week in 2018...”
- Review left on 03/12/2017

$430.00

Excellent (2 reviews)

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from $430.00 / night