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

Wailea-Makena Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Wailea-Makena holiday rentals

A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

1. 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 AU$862
includes taxes & fees
28 Sept - 29 Sept
The Residences at Kamaole Sands Resort
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

2. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (39 reviews)
"It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose"
United States
Roark
The price is AU$772
includes taxes & fees
27 Sept - 28 Sept
Signature Residences at Maui Banyan
A beach with palm trees and a clear sky.

3. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Wailea
10.0 out of 10, Exceptional, (164 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
The price is AU$778
includes taxes & fees
26 Sept - 27 Sept
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A residential area with a two-story building, a staircase, and various trees and shrubs.

4. Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
Wailea
10.0 out of 10, Exceptional, (38 reviews)
"Location location location! Just 1 block from the shops and Wailea beach…can’t beat that! "
United States
david k.
The price is AU$625
includes taxes & fees
1 Oct - 2 Oct
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A swimming pool with lounge chairs, a covered seating area, and palm trees in the background.

5. Beautiful Ocean View Studio!

Beautiful Ocean View Studio!
South Kihei
9.6 out of 10, Exceptional, (19 reviews)
"We loved the location and partial ocean view from the balcony. Easy walk to the beach and we had everything available that we needed for a comfortable stay. "
United States
Susan C.
The price is AU$621
includes taxes & fees
13 Oct - 14 Oct
Beautiful Ocean View Studio!
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

6. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (63 reviews)
"The condo property was beautiful and in a great location. We had to book last minute due to storms affecting our initial booking and host was very responsive. "
United States
Kathryn R.
The price is AU$526
includes taxes & fees
30 Sept - 1 Oct
Romantic 1 BR Condo with King Tempurpedic
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

7. Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
South Kihei
9.2 out of 10, Wonderful, (91 reviews)
"Location was perfect. We were there right after all of the flooding and the road was damaged but did not affect our stay at all. Our host was always responsive and made sure we were comfortable! Would surely stay again.:)"
United States
Melissa P.
The price is AU$627
includes taxes & fees
30 Sept - 1 Oct
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A spacious room with a large wooden dining table, comfortable seating, a bookshelf, and a view of the ocean through large sliding doors.

8. 180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
9.8 out of 10, Exceptional, (7 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is AU$948
includes taxes & fees
26 Sept - 27 Sept
180 Degree Ocean View in Wailea! WE204
A pathway leading to a beach with dense green foliage on either side.

9. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
South Kihei
9.8 out of 10, Exceptional, (97 reviews)
"Kitchen was fully equipped. Condo was very clean and host was promt with replys. Loved our stay "
Canada
Lori D.
The price is AU$790
includes taxes & fees
30 Sept - 1 Oct
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A tropical garden with a waterfall, palm trees, and a variety of lush greenery.

10. Wailea Luxury Retreat | Walk to Beach & Shops

Wailea Luxury Retreat | Walk to Beach & Shops
Wailea
9.4 out of 10, Exceptional, (8 reviews)
"Excellent communication and the facilities were really nice with Two pools to choose from! Close to shops and walking paths "
United States
Jennifer A.
The price is AU$825
includes taxes & fees
26 Sept - 27 Sept
Wailea Luxury Retreat | Walk to Beach & Shops
A sandy beach with footprints, a few people, and a boat.

11. 1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
South Kihei
9.4 out of 10, Exceptional, (61 reviews)
The price is AU$552
includes taxes & fees
26 Sept - 27 Sept
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
A pool area with lounge chairs, palm trees, and a covered seating area.

12. Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C

Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
South Kihei
9.8 out of 10, Exceptional, (133 reviews)
"We had a great stay at the condo. The location was perfect. The condo was spotless and the amenities very useful, especially all the beach equipment. And thanks for the snacks and candy that were there when we arrived."
United States
Bob J.
Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
A swimming pool with lounge chairs and a covered area, surrounded by palm trees and a clear sky.

13. One Bedroom Ocean View

One Bedroom Ocean View
South Kihei
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$608
includes taxes & fees
25 Sept - 26 Sept
One Bedroom Ocean View
An aerial view of a coastal resort with a beach, ocean, and a mountain in the background.

14. King Bed, Ocean View, AC, Pool, Walk to Beach

King Bed, Ocean View, AC, Pool, Walk to Beach
South Kihei
9.6 out of 10, Exceptional, (56 reviews)
"Full Kitchen, beach chair and cooler "
United States
Candace B.
King Bed, Ocean View, AC, Pool, Walk to Beach
An aerial view of a coastal area with a beach, a mountain in the background, and a hotel complex with multiple buildings.

15. Partial Ocean View, Pool, WiFi, Walk to Beach, ACs

Partial Ocean View, Pool, WiFi, Walk to Beach, ACs
South Kihei
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful and excellent location"
United States
Michael K.
The price is AU$605
includes taxes & fees
28 Sept - 29 Sept
Partial Ocean View, Pool, WiFi, Walk to Beach, ACs
A resort with a swimming pool, palm trees, and ocean views.

16. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (975 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is AU$545
includes taxes & fees
27 Sept - 28 Sept
Aston Maui Hill
A beach with people swimming and sunbathing, palm trees, and a building in the background.

17. 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, (167 reviews)
"Great location!"
United States
Tyler B.
The price is AU$521
includes taxes & fees
30 Sept - 1 Oct
Across from Kamaole 2 Beach, concrete building, well maintained.
A resort pool area with a view of the ocean and a golf course in the background.

18. DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose
Wailea
9.8 out of 10, Exceptional, (186 reviews)
"Proximity to ocean was amazing..great place to start a morning walk to Wailea Beach walk..well stalked condominium…amazing sound system..Comfortable bed and beautiful artwork..will definitely plan another visit here.."
United States
Tim T.
The price is AU$755
includes taxes & fees
9 Oct - 10 Oct
DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose
A hotel with a view of the ocean, surrounded by palm trees and a parking lot.

19. 5th Floor Oceanview Retreat Steps from the Beach + new split AC !

5th Floor Oceanview Retreat Steps from the Beach + new split AC !
South Kihei
9.4 out of 10, Exceptional, (94 reviews)
"The condo was great very comfortable nice and clean also in a very good location"
United States
Holly P.
The price is AU$589
includes taxes & fees
30 Sept - 1 Oct
5th Floor Oceanview Retreat Steps from the Beach + new split AC !
A swimming pool with a hot tub, surrounded by lush greenery and palm trees, with a view of the ocean and hotel buildings in the background.

20. COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
Wailea
9.8 out of 10, Exceptional, (129 reviews)
"Wonderful, modern, great location condo!"
United States
Jaclyn G.
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wailea-Makena Hotel Reviews

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"I loved the cleanliness of the hotel as well as the exceptional staff. Everyone was so polite and welcoming."
Tiffany 17-night trip
Posted 2 hours ago
Wailea Beach Resort - Marriott, Maui

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 favourite 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 depend 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 AU$545 per night. Entering your travel dates in the search wizard might find you 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. 

Explore a world of travel with Expedia