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Vacation Homes in Wailea

Find the vacation homes that appeal to you the most

August 2026

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Vacation Homes for every style

Find the right vacation home for you in Wailea

The best vacation homes in Wailea

Check out our selection of great vacation homes 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

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

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
$540.65
1 night, 2 adults

Perch - Luana Kai Loft C308

Kihei (Near Wailea)

Perch - Luana Kai Loft C308 offers accommodations in Kihei, a 2-minute walk from Waipuilani Beach and 6.8 miles from Wailea Emerald Course. This beachfront property offers access to a balcony.

M
Michael
From
United States
Clean and well supplied. Responsive to questions. Location was fine.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 5 reviews
Price from
$437.68
1 night, 2 adults

Hale Kai O'Kihei 305

Kihei (Near Wailea)

6.6 miles from Wailea Emerald Course in Kihei, Hale Kai O'Kihei 305 features accommodations with access to a spa center. The air-conditioned accommodation is a 7-minute walk from Waipuilani Beach.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 5 reviews
Price from
$662.60
1 night, 2 adults

Stunning ocean view 2 bedroom Steps from beach

Kihei (Near Wailea)

Stunning ocean view 2 bedroom Steps from beach offers accommodations in Kihei, a 1-minute walk from Kamaole Beach and 4 miles from Wailea Emerald Course.

V
Virginia
From
United States
The view, the openness and lightness, the lanai, the cleanliness.
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 13 reviews
Price from
$480.44
1 night, 2 adults

Hale Kai O'Kihei 120

Kihei (Near Wailea)

6.6 miles from Wailea Emerald Course in Kihei, Hale Kai O'Kihei 120 provides accommodations with access to a spa center. The air-conditioned accommodation is a 7-minute walk from Waipuilani Beach.

V
Virangi
From
United States
Location was excellent. Right on beach
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 12 reviews
Price from
$554.44
1 night, 2 adults

Maui Vista 1411

Kihei (Near Wailea)

4.4 miles from Wailea Emerald Course in Kihei, Maui Vista 1411 offers accommodations with access to a spa center. The air-conditioned accommodation is a 5-minute walk from Kamaole Beach.

T
Terry
From
United States
Very comfortable beds. Nice to have extras in the room for the beach etc. great location
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 18 reviews
Price from
$652.60
1 night, 2 adults

Suite Maui Paradise Condo

Wailuku (Near Wailea)

Just a few steps from Maalaea Beach and a 12-minute walk from Maui Ocean Center, Suite Maui Paradise Condo features accommodations in Wailuku with an outdoor swimming pool.

Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 9 reviews
Price from
$333.62
1 night, 2 adults

Charming Beachside Garden Vistas

Wailea

Charming Beachside Garden Vistas offers a fitness room and free private parking, and is within a 4-minute walk of Kamaole Beach and 3.8 miles of Wailea Emerald Course.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
All vacation homes in Wailea

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

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

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Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Wailea

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

Popular with guests booking vacation homes in Wailea

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

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 24 reviews

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 4 reviews

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Wailea

Scored out of 10, guest rating 7.2
Good - What previous guests thought, 6 reviews

Popular with guests booking vacation homes in Wailea

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

Vacation Homes 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, 2 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

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 4 reviews
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 6 reviews

Save money on vacation homes in Wailea and nearby – budget options available

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Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 24 reviews

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

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

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 34 reviews

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 5 reviews

Great access to the city center. Check these vacation homes in Wailea and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 3 reviews

FAQ about vacation homes in Wailea

Vacation Homes That Guests Love in Wailea

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Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 45 reviews
Fantastic views, close to beautiful beaches. Nice walk nearby. Spotted a few turtles too.The sunset from the property was amazing! Very friendly host and onsite staff. Property was very clean and well equipped. We were a family of 4 with young kids but this place is also perfect for a group of friends and couples. Highly recommend this place.
Guest review byPARVATHA
Family with young children
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 21 reviews
The apartment is very clean, and we like the location so close Wailea. We also like the assigned parking is just outside the apartment and the unit is on the ground level. Checkin instructions are accurate and easy to follow.
Guest review byLinette
Young couple