Wailea-Makena Holiday Rentals

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Our top choices for Wailea-Makena holiday rentals

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (857)
"Clean room, attentive staff, and tons of things for kids and adults alike to do! "
United States
Misty
The price is NZ$924
includes taxes & fees
6 Jan - 7 Jan 2026
Aston Maui Hill

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
4.5 star property
South Kihei
9.6 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
The price is NZ$1,003
includes taxes & fees
1 Jan - 2 Jan 2026
Signature Residences at Maui Banyan

Polo Beach - CoralTree Residence Collection

Polo Beach - CoralTree Residence Collection
3.5 star property
Wailea
9.0 out of 10, Wonderful, (62)
"Looking forward to booking again"
United States
robert
The price is NZ$1,451
includes taxes & fees
14 Jan - 15 Jan 2026
Polo Beach - CoralTree Residence Collection

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
3.0 star property
Wailea
10.0 out of 10, Exceptional, (1)
"Beautiful place"
United States
Armando
The price is NZ$2,245
includes taxes & fees
7 Jan - 8 Jan 2026
Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
The price is NZ$1,860
includes taxes & fees
31 Dec - 1 Jan 2026
The Residences at Kamaole Sands Resort

Beautiful Ocean View Studio at Kihei Akahi

Beautiful Ocean View Studio at Kihei Akahi
South Kihei
10.0 out of 10, Exceptional, (10)
"Happy.Would come again. 5 min walk to the beach."
United States
lloyd i.
The price is NZ$787
includes taxes & fees
24 Jan - 25 Jan 2026
Beautiful Ocean View Studio at Kihei Akahi

Kihei Retreat w/ Kamaole Sands Resort Amenities!

Kihei Retreat w/ Kamaole Sands Resort Amenities!
3.5 star property
South Kihei
The price is NZ$1,353
includes taxes & fees
6 Jan - 7 Jan 2026
Kihei Retreat w/ Kamaole Sands Resort Amenities!

Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper

Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper
South Kihei
9.6 out of 10, Exceptional, (109)
"Excellent"
United States
Norma Darleen O.
The price is NZ$966
includes taxes & fees
18 Jan - 19 Jan 2026
Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper

Kamaole Sands Condos Close to Beach with Parking

Kamaole Sands Condos Close to Beach with Parking
3.5 star property
South Kihei
9.0 out of 10, Wonderful, (2)
"Clean property nice room good location"
United States
Richard
The price is NZ$923
includes taxes & fees
8 Jan - 9 Jan 2026
Kamaole Sands Condos Close to Beach with Parking

Oceanview King Studio | Maui Banyan, Walk to Beach

Oceanview King Studio | Maui Banyan, Walk to Beach
2.0 star property
South Kihei
10.0 out of 10, Exceptional, (1)
"Great location, beautiful unit. Fabulous sunsets, couldn’t have been happier with our choice! Would recommend this unit to anyone traveling to south Kihei Hawaii!"
United States
Richard C.
The price is NZ$805
includes taxes & fees
3 Jan - 4 Jan 2026
Oceanview King Studio | Maui Banyan, Walk to Beach

~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~

~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~
Wailea
10.0 out of 10, Exceptional, (136)
"Super easy to get to, great location, plenty of room, good A/C—superb communication in advance from owner to make arrival a breeze! Enjoyed it!"
United States
Christopher B.
The price is NZ$1,143
includes taxes & fees
14 Jan - 15 Jan 2026
~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~

Across from Kamaole 2 Beach, concrete building, well maintained.

Across from Kamaole 2 Beach, concrete building, well maintained.
South Kihei
10.0 out of 10, Exceptional, (151)
"This is my home away from home! Very clean and comfortable, walking convenience to a beautiful beach, wonderful restaurants and a variety of shopping. Most importantly a feeling of safety and community. Here you have all of this and more! "
United States
Julie L.
The price is NZ$784
includes taxes & fees
13 Jan - 14 Jan 2026
Across from Kamaole 2 Beach, concrete building, well maintained.

Polo Beach Club 407 - 2 Bedroom Oceanfront Condo

Polo Beach Club 407 - 2 Bedroom Oceanfront Condo
2.0 star property
Wailea
10.0 out of 10, Exceptional, (7)
"Loved the proximity to the beach and the Fairmont! All around a wonderful place and great place to stay!"
United States
Shane W.
The price is NZ$2,181
includes taxes & fees
3 Jan - 4 Jan 2026
Polo Beach Club 407 - 2 Bedroom Oceanfront Condo

Palms 501 2 Bedroom Condo

Palms 501 2 Bedroom Condo
3.0 star property
Wailea
The price is NZ$1,824
includes taxes & fees
15 Jan - 16 Jan 2026
Palms 501 2 Bedroom Condo

Oceanview Newly Remodeled Across from Kamaole 3 Beach

Oceanview Newly Remodeled Across from Kamaole 3 Beach
South Kihei
10.0 out of 10, Exceptional, (2)
"Spacious and clean. Great place for family and access to beach. All amenities included. "
United States
Dustin
The price is NZ$1,080
includes taxes & fees
20 Jan - 21 Jan 2026
Oceanview Newly Remodeled Across from Kamaole 3 Beach

Top Floor Mana Kai, "Ali'i Level", Incredible Views, Fully Air Conditioned

Top Floor Mana Kai, "Ali'i Level", Incredible Views, Fully Air Conditioned
South Kihei
9.8 out of 10, Exceptional, (83)
"Great location with beach access and snorkeling. Excellent onsite amenities. Highly recommend and would stay here again. "
United States
Cary S.
Top Floor Mana Kai, "Ali'i Level", Incredible Views, Fully Air Conditioned

Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC

Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC
2.0 star property
Wailea
10.0 out of 10, Exceptional, (1)
"The unit was close to the pool and the entrance to the beach. The unit was very clean and it had everything we needed. The AC stopped working on our second day and we reached out to the operations manager. They were so quick to dispatch someone to fix the issue. We would definitely stay here again. "
United States
Maria D.
Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC

Opulent Remodel, Steps To Beach! HSA206

Opulent Remodel, Steps To Beach! HSA206
2.0 star property
South Kihei
10.0 out of 10, Exceptional, (3)
"We loved this location for our stay in Kihei. Able to walk down to the beach was great for our trip. The apartment was clean and great for our family. Would definitely stay here again. "
United States
Chris M.
The price is NZ$1,348
includes taxes & fees
3 Jan - 4 Jan 2026
Opulent Remodel, Steps To Beach! HSA206

Maui Kamaole Kihei Resort I Beaches, Pools, Tennis

Maui Kamaole Kihei Resort I Beaches, Pools, Tennis
South Kihei
9.4 out of 10, Exceptional, (53)
"Love staying at the Maui Kamaole."
Canada
larry w.
The price is NZ$1,456
includes taxes & fees
27 Jan - 28 Jan 2026
Maui Kamaole Kihei Resort I Beaches, Pools, Tennis

Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.

Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
South Kihei
10.0 out of 10, Exceptional, (213)
"We enjoyed every minute of our stay. We couldn’t be happier!!! We will definitely be back!!Cheers!!"
United States
Dan H.
The price is NZ$895
includes taxes & fees
15 Jan - 16 Jan 2026
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
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

Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wailea-Makena holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wailea-Makena holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wailea-Makena. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wailea-Makena holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wailea-Makena holiday rentals we have selected for you start as low as NZ$924 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

At Expedia, we put the best Wailea-Makena holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wailea-Makena rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wailea-Makena holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wailea-Makena. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.