A coastal landscape with rocky cliffs, a body of water, and a distant mountain range under a cloudy sky.

Wailea-Makena Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Wailea-Makena vacation rentals

A resort with a swimming pool, palm trees, and ocean views.

1. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (988 reviews)
"Way more than what we expected.. clean, well kept, extremely spacious and centrally located to shops, beaches and restaurants. Loved everything about the property"
United States
Michael
The price is ₩441,920
₩524,612 total
includes taxes & fees
Nov 8 - Nov 9
Aston Maui Hill
A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

2. Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (5 reviews)
"Clean everything great time great location! "
United States
Sean
The price is ₩584,232
₩1,350,530 total
includes taxes & fees
Oct 10 - Oct 11
Grand Champions by KBM
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

3. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (40 reviews)
"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."
United States
Mai
The price is ₩91,871
₩753,985 total
includes taxes & fees
Oct 12 - Oct 13
Signature Residences at Maui Banyan
A resort pool area with a hot tub, lounge chairs, and palm trees.

4. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is ₩1,238,066
₩2,228,517 total
includes taxes & fees
Oct 12 - Oct 13
Villa, Garden View, 2-bedroom
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

5. The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas"
United States
George Lucas
The price is ₩126,850
₩827,812 total
includes taxes & fees
Oct 13 - Oct 14
The Residences at Kamaole Sands Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wailea-Makena Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

8/10 Good
"10/5/26 - Once I got over the beauty of the island and its surroundings on day one, I began to assess what was around me from my room to the hotel grounds as well as the service being provided. I began to compare the amenities and service of the Grand Wailea to the Peninsula Hotel in Chicago where I stayed in July, 2026. There are some significant differences. Staying at a “luxury hotel” does not always mean the same level of luxury. For instance, I looked back at my arrival to the hotel and realized that no one offered to help me with my bag. I arrived early, so my room was not yet ready. I checked my bag with the bellhop. When my room was eventually ready, the bellhop did not bring my bag to my room. I had to retrieve it myself. Although staff seemed sparse, most were extremely helpful. There appeared to be a lot of landscaping staff maintaining the grounds which were quite beautiful. My wooden patio furniture was weather beaten and had not been oiled or stained in quite some time. The typical luxury items that are expected to be in a luxury ocean view suite were not available such as snacks, bar items and other soft drinks. There was no honor bar and the refrigerator was completely empty. I was supplied with two bottles of water for the entire stay with no replacement. However, there was a lounge on 8 with snacks available. The ambiance was more of a family gathering spot. Most hotel guests were families with young children, toddlers and infants."
Charles Thomas 3-night trip
Posted 1 hour ago
Grand Wailea Maui, A Waldorf Astoria Resort

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