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Wailea 3-bedroom Vacation Rentals, Apartments & More - 44 Rentals Available.

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44 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

$1,550.00

Excellent (2 reviews)

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from $1,550.00 / night

(13)

1 / 24

Wailea Apartment

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

$275.00

Very Good (13 reviews)

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from $275.00 / night

(8)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (8 reviews)

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from $1,495.00 / night

(12)

1 / 30

Wailea Apartment

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

$1,569.00

Excellent (12 reviews)

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from $1,569.00 / 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)

1 / 50

Wailea House

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

$2,095.00

Excellent (1 reviews)

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from $2,095.00 / night

1 / 50

Wailea House

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

$2,850.00

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from $2,850.00 / night

(4)

1 / 50

Wailea House

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

$1,651.00

Very Good (4 reviews)

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from $1,651.00 / night

1 / 24

Wailea Apartment

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

$519.00

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from $519.00 / night

1 / 50

Wailea House

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

$1,596.00

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from $1,596.00 / night

(13)

1 / 50

Wailea House

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

$4,500.00

Very Good (13 reviews)

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from $4,500.00 / night

(10)

1 / 50

Wailea Villa

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

$1,450.00

Excellent (10 reviews)

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from $1,450.00 / night

1 / 24

Wailea Apartment

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

$950.00

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from $950.00 / night

(6)

1 / 50

Wailea Villa

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

$2,950.00

Excellent (6 reviews)

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from $2,950.00 / night

(6)

1 / 50

Wailea House

  • 4
  • 8
  • min stay varies
  • 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

$1,495.00

Excellent (7 reviews)

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from $1,495.00 / night

(7)

1 / 49

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

$2,195.00

Excellent (9 reviews)

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from $2,195.00 / night

(9)

1 / 50

Wailea Villa

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

$1,925.00

Excellent (9 reviews)

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from $1,925.00 / night

(1)

1 / 50

Wailea Villa

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

$1,550.00

Excellent (1 reviews)

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from $1,550.00 / night

(2)

1 / 50

Wailea Villa

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

$1,450.00

Excellent (2 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

$1,695.00

Excellent (1 reviews)

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from $1,695.00 / night

(2)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (2 reviews)

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from $1,495.00 / night

(3)

1 / 50

Wailea Villa

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

$2,250.00

Very Good (3 reviews)

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from $2,250.00 / night

(11)

1 / 50

Wailea Villa

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

$1,795.00

Excellent (11 reviews)

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from $1,795.00 / 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

1 / 47

Wailea House

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

$3,595.00

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from $3,595.00 / night

Your search has been expanded 18 miles to include more rentals

(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

(3)

1 / 37

Kula House - 10.3 miles away

  • 3
  • 8
  • min stay varies
  • 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

(14)

1 / 24

Kihei Apartment - 5.4 miles away

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

$435.00

Very Good (14 reviews)

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from $435.00 / night

(18)

1 / 24

Kihei Apartment - 5.4 miles away

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

$514.00

Very Good (18 reviews)

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from $514.00 / night

(21)

1 / 24

Kihei Apartment - 2.3 miles away

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

$519.00

Very Good (21 reviews)

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from $519.00 / night

(4)

1 / 24

Kihei Apartment - 2.3 miles away

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

$519.00

Average (4 reviews)

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from $519.00 / night

(4)

1 / 24

Kihei Apartment - 2.3 miles away

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

$519.00

Very Good (4 reviews)

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from $519.00 / night

(1)

1 / 32

Kihei Condo - 0.1 miles away

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

$881.00

Excellent (1 reviews)

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from $881.00 / night

1 / 24

Kihei Apartment - 2.3 miles away

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

$519.00

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from $519.00 / night

(2)

1 / 24

Kihei Apartment - 2.3 miles away

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

$619.00

Very Good (2 reviews)

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from $619.00 / night

(12)

1 / 50

Kihei House - 4.1 miles away

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

$2,500.00

Excellent (12 reviews)

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from $2,500.00 / night