Search 105,200+ Vacation Rentals
✕

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

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

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

Book

from $2,165.00 / night

Book

(101)

1 / 42

Wailea Villa

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,140.00

Excellent (101 reviews)

Book

from $1,140.00 / night

Book

(2)

1 / 50

Wailea House

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

$1,195.00

Excellent (2 reviews)

Inquire

from $1,195.00 / night

Inquire

(8)

1 / 50

Wailea Villa

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

$995.00

Excellent (8 reviews)

Inquire

from $995.00 / night

Inquire

(1)

1 / 50

Wailea House

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

$1,695.00

Excellent (1 reviews)

Inquire

from $1,695.00 / night

Inquire
1 / 50

Wailea House

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

$2,850.00

Inquire

from $2,850.00 / night

Inquire

(13)

1 / 50

Wailea House

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

$2,950.00

Very Good (13 reviews)

Inquire

from $2,950.00 / night

Inquire

(1)

1 / 50

Wailea House

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

$2,900.00

Excellent (1 reviews)

Inquire

from $2,900.00 / night

Inquire

(4)

1 / 50

Wailea House

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

$1,450.00

Very Good (4 reviews)

Inquire

from $1,450.00 / night

Inquire
1 / 50

Wailea House

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

$1,195.00

Inquire

from $1,195.00 / night

Inquire

(6)

1 / 50

Wailea Villa

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

$2,145.00

Excellent (6 reviews)

Inquire

from $2,145.00 / night

Inquire

(10)

1 / 50

Wailea Villa

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

$995.00

Excellent (10 reviews)

Inquire

from $995.00 / night

Inquire

(9)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (9 reviews)

Inquire

from $1,595.00 / night

Inquire

(6)

1 / 50

Wailea House

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

$1,695.00

Excellent (6 reviews)

Inquire

from $1,695.00 / night

Inquire

(7)

1 / 50

Wailea House

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

$1,195.00

Excellent (7 reviews)

Inquire

from $1,195.00 / night

Inquire

(1)

1 / 50

Wailea Villa

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

$1,250.00

Excellent (1 reviews)

Inquire

from $1,250.00 / night

Inquire

(9)

1 / 50

Wailea Villa

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

$1,495.00

Excellent (9 reviews)

Inquire

from $1,495.00 / night

Inquire

(2)

1 / 50

Wailea Villa

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

$995.00

Excellent (2 reviews)

Inquire

from $995.00 / night

Inquire

(7)

1 / 50

Wailea Villa

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

$995.00

Excellent (7 reviews)

Inquire

from $995.00 / night

Inquire

(2)

1 / 50

Wailea Villa

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

$1,150.00

Excellent (2 reviews)

Inquire

from $1,150.00 / night

Inquire

(1)

1 / 50

Wailea Villa

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

$1,595.00

Excellent (1 reviews)

Inquire

from $1,595.00 / night

Inquire

(3)

1 / 50

Wailea Villa

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

$1,595.00

Very Good (3 reviews)

Inquire

from $1,595.00 / night

Inquire

(2)

1 / 50

Wailea House

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

$2,095.00

Very Good (2 reviews)

Inquire

from $2,095.00 / night

Inquire

(11)

1 / 50

Wailea Villa

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

$1,395.00

Excellent (11 reviews)

Inquire

from $1,395.00 / night

Inquire

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)

Book

from $602.00 / night

Book

(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)

Book

from $516.00 / night

Book

(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)

Book

from $802.00 / night

Book

(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)

Book

from $916.00 / night

Book

(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)

Inquire

from $245.00 / night

Inquire

(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)

Inquire

from $259.00 / night

Inquire

(2)

1 / 19

Makawao House - 14 miles away

  • 4
  • 8
  • 4 nights min

$295.00

Average (2 reviews)

Inquire

from $295.00 / night

Inquire

(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)

Inquire

from $872.00 / night

Inquire

(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)

Book

from $1,802.00 / night

Book

(1)

1 / 10

Makawao House - 14 miles away

  • 3
  • 6
  • 4 nights min

$295.00

Excellent (1 reviews)

Inquire

from $295.00 / night

Inquire

(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)

Inquire

from $421.00 / night

Inquire

(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)

Inquire

from $1,495.00 / night

Inquire

(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)

Inquire

from $1,896.00 / night

Inquire

(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)

Inquire

from $2,600.00 / night

Inquire
1 / 50

Kihei Villa - 0.1 miles away

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

$2,825.00

Inquire

from $2,825.00 / night

Inquire
1 / 50

Kihei Villa - 0.1 miles away

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

$1,095.00

Inquire

from $1,095.00 / night

Inquire