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Vacation Rentals in Wailea

Find the vacation rentals that appeal to you the most

August 2026

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The best vacation rentals in Wailea

Check out our selection of great vacation rentals in Wailea

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Enjoy Your Oceanside Dream at Kihei Surfside

Wailea

Providing a garden, Enjoy Your Oceanside Dream at Kihei Surfside provides accommodations in Wailea. This beachfront property offers access to a balcony and free Wifi.

M
Michael
From
United States
Everything about Kihei Surfside was wonderful! Fantastic location, great facility, super helpful staff, and a very comfortable unit. We will certainly look to stay here again on our next visit to Maui.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews
Price from
$398.10
1 night, 2 adults

Mana Kai 710A

Wailea

Mana Kai 710A is located in Wailea, just a 3-minute walk from Keawakapu Beach and 3 miles from Wailea Emerald Course. Featuring sea views, this apartment also features free Wifi.

M
Madison
From
United States
Right on the beach, ocean view, spacious, updated appliances, nice patio, family friendly area. Beach was very sandy and sea turtles right on the beach. Good snorkeling on beach. Mana Kai is a great resort to stay! Unit had 2 small beach chairs and 2 beach umbrellas to use. Had 4 beach towels. Coin/card washer/dryer across the hall if needing to do laundry.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 11 reviews
Price from
$609.50
1 night, 2 adults

Aston Maui Hill

Hotel in Wailea

Featuring spacious suites with fully-equipped kitchens, this Kihei resort is 6 minutes' walk from Kamaole Beach Park III. The resort features a heated outdoor pool and hot tub.

A
Angela
From
United Kingdom
Great facilities, massive unit, really clean, lovely staff, within walking distance to the beach
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 407 reviews
Price from
$349
1 night, 2 adults

Aston at the Maui Banyan

Hotel in Wailea

Located directly across the road from Kamaole Beach Park II and 14 mi from Kahului Airport, the Aston at the Maui Banyan features outdoor swimming pool.

C
Cynthia
From
Canada
Centrally located. Super comfortable, friendly staff. Peaceful and pretty gardens. Great pools and close to the beach and shops
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 253 reviews
Price from
$254
1 night, 2 adults

Upscale Wailea! 2-2 with Ocean View

Wailea

Just 1.1 miles from Wailea Emerald Course and 1.1 miles from Wailea Blue Course, Upscale Wailea!

J
Jacqueline
From
United States
There was not any breakfast. the condo was perfect with a view of Maui waters, saw whale from the lanai...
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 6 reviews
Price from
$636.20
1 night, 2 adults

Mana Kai 711C

Wailea

Mana Kai 711C is located in Wailea, just a 3-minute walk from Keawakapu Beach and 3 miles from Wailea Emerald Course. Featuring sea views, this apartment also features free Wifi.

J
Jacqueline
From
United States
Location and cleanliness - accommodations very nice !
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 5 reviews
Price from
$801.76
1 night, 2 adults

8-403 Kamaole Sands

Wailea

8-403 Kamaole Sands is located in Wailea, just a 7-minute walk from Kamaole Beach and 3.3 miles from Wailea Emerald Course.

V
Vanessa
From
United States
Clean & a great location.
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews
Price from
$553.98
1 night, 2 adults

Beautiful Condo at Kihei Ali'i Kai, Close to Beach

Kihei (Near Wailea)

A few steps from Kamaole Beach in Kihei, Beautiful Condo at Kihei Ali'i Kai, Close to Beach features accommodations with access to a sauna and hot tub.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 23 reviews
Price from
$525.34
1 night, 2 adults

Kihei Ali'i Kai Condo with King Bed, 55'' Smart TV, Free Parking!

Kihei (Near Wailea)

A few steps from Kamaole Beach in Kihei, Kihei Ali'i Kai Condo with King Bed, 55'' Smart TV, Free Parking! features accommodations with access to a sauna and hot tub.

D
Danilo
From
United States
Excellent location, clean and quiet. Accessories for beach outing provided.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews
Price from
$488.33
1 night, 2 adults

Maui Tranquility II

Kihei (Near Wailea)

Maui Tranquility II offers accommodations in Kihei, a 1-minute walk from Kamaole Beach and 3.8 miles from Wailea Emerald Course.

D
DORAH-LEIGH
From
United States
Nice property at a competitive price. In the heart of what’s happening. Everything was in walking distance. The owners were highly responsive. I plan to stay there again in the future. Go ahead and book the property you won’t regret. Nice place for the average vacationer wanting a clean, great location at a good price. You have found the spot.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 31 reviews
Price from
$348
1 night, 2 adults
All vacation rentals in Wailea

Most booked vacation rentals in Wailea and surrounding area in the past month

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Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 253 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 407 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 67 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 236 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 26 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 44 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 36 reviews

Popular with guests booking vacation rentals in Wailea

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 23 reviews

Vacation Rentals with swimming pools in Wailea and nearby

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Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 253 reviews

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 407 reviews

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 236 reviews

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 26 reviews

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 44 reviews

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 36 reviews

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews

These vacation rentals in Wailea and nearby have options with free cancellation

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Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 67 reviews

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 23 reviews

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 9 reviews

Kihei Akahi C-513

2531 S. Kihei Rd, Kihei Akahi C-513
Free cancellation options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Ekolu 1403

10 Waliea Ekolu Place, 1403
Free cancellation options available
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 4 reviews
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 46 reviews

Kamaole Sands 2-106

Free cancellation options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 7 reviews

Highly rated vacation rentals in Wailea and nearby

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Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 21 reviews

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 8 reviews

Maui Kamaole D208

8.0+ review score
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 10 reviews

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 6 reviews

Scored out of 10, guest rating 6.5
Pleasant - What previous guests thought, 27 reviews

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 6 reviews

Maui Kamaole G208

8.0+ review score
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 10 reviews

FAQ about vacation rentals in Wailea

On average, a vacation rental in Wailea costs $276 per night (based on Booking.com prices).
The average price per night for a vacation rental in Wailea this weekend is $860 (based on Booking.com prices).
The average price of a vacation rental in Wailea this evening is $597 (based on Booking.com prices).
For vacation rentals in Wailea serving highly-rated breakfasts, try Maui What a Wonderful World Bed & Breakfast, Aston Maui Hill, and Kamaole Sands Walk to Sand, Shops and Restaurants.