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

Wailea-Makena Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Wailea-Makena holiday 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, (1,003 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is AU$511
includes taxes & fees
8 Dec - 9 Dec
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 AU$1,619
includes taxes & fees
30 Nov - 1 Dec
Grand Champions by KBM
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, (165 reviews)
"Everything was amazing, I enjoyed all the amenities the room had to offer. Will definitely book again in the future."
United States
Rojelio G.
The price is AU$951
includes taxes & fees
10 Nov - 11 Nov
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

4. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (65 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$539
includes taxes & fees
18 Nov - 19 Nov
Romantic 1 BR Condo with King Tempurpedic
A wooden table with a bottle of wine and two glasses on a balcony overlooking a lush garden and the ocean.

5. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Wailea
9.8 out of 10, Exceptional, (194 reviews)
"Amazing view, good size spaces nice proximity to the shops in Wailea. Overall great stay."
United States
Scott M.
The price is AU$870
includes taxes & fees
18 Nov - 19 Nov
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A resort with a swimming pool, palm trees, and hanging decorative spheres.

6. Wailea Ekahi 29C, Ocean View, Steps away from the pool

Wailea Ekahi 29C, Ocean View, Steps away from the pool
Wailea
10.0 out of 10, Exceptional, (92 reviews)
"Perfect spot and location for our spring break getaway. This unit has lots of amenities available just steps away. "
United States
Corey R.
The price is AU$1,494
includes taxes & fees
6 Dec - 7 Dec
Wailea Ekahi 29C, Ocean View, Steps away from the pool
A spacious living area with a glass table, wooden chairs, a sofa, and a view of the ocean through large windows.

7. Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Wailea
10.0 out of 10, Exceptional, (76 reviews)
"Great place to stay for your vacation!"
United States
Nick D.
The price is AU$1,290
includes taxes & fees
4 Dec - 5 Dec
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
An outdoor patio with a grill, seating, and a view of the ocean.

8. Ekahi 27A: Priceless Ocean View from a Private Lanai

Ekahi 27A: Priceless Ocean View from a Private Lanai
Wailea
9.8 out of 10, Exceptional, (58 reviews)
"Amazing sunsets, good privacy, a smaller quiet pool nearby, kitchen is well equipped."
United States
Petr K.
Ekahi 27A: Priceless Ocean View from a Private Lanai
An aerial view of a hotel with a central swimming pool, multiple lounge areas, and lush greenery.

9. Luxury Condo on Wailea Blue Golf Course

Luxury Condo on Wailea Blue Golf Course
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"Very nice condo. Accommodated everything we needed for a wonderful vacation."
United States
Bryce
The price is AU$1,018
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo on Wailea Blue Golf Course
A resort with a central pool, palm trees, and a well-maintained lawn.

10. Romantic, Luxury Maui Getaway with Ocean View - Couples Only

Romantic, Luxury Maui Getaway with Ocean View - Couples Only
Wailea
10.0 out of 10, Exceptional, (22 reviews)
"Just a wonderful stay. Everything is just right and the property is beautiful. "
United States
Roger B.
The price is AU$908
includes taxes & fees
17 Nov - 18 Nov
Romantic, Luxury Maui Getaway with Ocean View - Couples Only
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

11. Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
Wailea
10.0 out of 10, Exceptional, (82 reviews)
"Great location near beach, the shops at Wailea, golf courses, restaurants, . . . .Host responded quickly and thoughtfully to any questions. The condo was clean and well stocked with beach toys like chairs, towels, . . .Very seamless move in and out. "
United States
Matthew M.
The price is AU$669
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A beach with clear turquoise water, a sandy shore, and a mountain in the background.

12. Wailea Ekahi Village WKV-45C by KBM

Wailea Ekahi Village WKV-45C by KBM
4.5 star property
Wailea
6.0 out of 10, (1 review)
"I did not like this location and would not go back. It’s on a lower floor, and kind of dark and musty. I left within a few hours of being there. But the host was very communicative and the location is great. I just wouldn’t personally stay here."
United States
Chelsea
The price is AU$1,844
includes taxes & fees
5 Dec - 6 Dec
Wailea Ekahi Village WKV-45C by KBM
A resort with a swimming pool, palm trees, and a view of the ocean.

13. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
Wailea
10.0 out of 10, Exceptional, (45 reviews)
"Great condo! "
Canada
Marcie M.
The price is AU$737
includes taxes & fees
1 Dec - 2 Dec
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
A beach with clear water, a sandy shore, and a building with a balcony overlooking the beach.

14. StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
Wailea
9.8 out of 10, Exceptional, (53 reviews)
"Great place to stay! We throughly enjoyed our time here "
United States
Emily B.
The price is AU$737
includes taxes & fees
30 Nov - 1 Dec
StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

15. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (41 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 AU$748
includes taxes & fees
10 Nov - 11 Nov
Signature Residences at Maui Banyan
A swimming pool with a curved design, surrounded by palm trees and a golf course.

16. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
Wailea
10.0 out of 10, Exceptional, (62 reviews)
"Great place and attentive owners"
United States
Darren P.
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A beach with a sunset, palm trees, and rocky outcrops.

17. Romantic, Luxury, Sensual Retreat - Couples Only

Romantic, Luxury, Sensual Retreat - Couples Only
Wailea
10.0 out of 10, Exceptional, (209 reviews)
"Just perfect! Amazing property and amazing location!"
United States
Jessica N.
The price is AU$976
includes taxes & fees
22 Nov - 23 Nov
Romantic, Luxury, Sensual Retreat - Couples Only
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

18. Cozy, Well-Furnished Studio

Cozy, Well-Furnished Studio
Wailea
9.0 out of 10, Wonderful, (71 reviews)
"Wonderful bed, slept very well. Large bathroom with plenty of counter space. A tiny tiny kitchenette. Had not realized that we’d have to stand on someone else’s balcony in front of their sliding glass doors, in order to do laundry, or that laundry could only be done in daylight hours. (It’s much preferable for us, while on vacation, to do laundry at night.) Well-stocked room. Would stay again."
United States
Lisa Q.
The price is AU$496
includes taxes & fees
28 Nov - 29 Nov
Cozy, Well-Furnished Studio
A pool area with palm trees, lounge chairs, and a view of the ocean.

19. Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
Wailea
10.0 out of 10, Exceptional, (21 reviews)
"This condo was incredible. Really well stocked kitchen for serious cooks. The bedrooms and bathrooms are large and comfortable. The living/dining room has a large TV and lots of comfortable seating. The hosts (Simone) were terrific, accommodating and were easy to communicate with. My two adult Son’s and their partners loved this condo."
United States
Sandi G.
The price is AU$1,875
includes taxes & fees
7 Dec - 8 Dec
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
A hotel room with a balcony, a desk, a chair, a bed, and a ceiling fan.

20. Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
South Kihei
9.2 out of 10, Wonderful, (19 reviews)
"The location of this unit is wonderful. Close to beach, parks, restaurants, and tennis. "
United States
Paul B.
The price is AU$855
includes taxes & fees
10 Nov - 11 Nov
Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
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

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

8/10 Good
"We stayed here for three nights for our Honeymoon. Excited to splurge on a luxury hotel brand for this special occasion. We were greeted by a bottle of champagne, which was lovely. Everything about the resort was top notch! BEWARE though, there is construction going on in the interior room areas of the property. The noise was so loud that we were unable to rest in the afternoons. Think jackhammer and metal grinding! We were advised upon check in that there was construction going on around the property. We thought that meant outdoor or general common areas, not adjacent to our sleeping room! We should have complained immediately after checking in, but we had already unpacked and were tired from traveling. Had we been made aware that our room was so close to loud construction upon checking in, that would have been different. We did have rain, so we weren't at the beach or pool much during the day. To spend $1660/night was reprehensible of the hotel staff not to clearly state the nuisance. We probably would have chosen to upgrade to a better room."
Rebecca 3-night trip
Posted less than an hour ago
Four Seasons Resort Maui at Wailea

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$511 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. 

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