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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (1,003 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
$289 nightly
The price is $343
Dec 9 - Dec 10
Total with taxes and fees
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
$990 nightly
The price is $1,175
Nov 30 - Dec 1
Total with taxes and fees
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, (166 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.
$485 nightly
The price is $570
Nov 11 - Nov 12
Total with taxes and fees
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.
$311 nightly
The price is $365
Nov 18 - Nov 19
Total with taxes and fees
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.
$511 nightly
The price is $599
Nov 18 - Nov 19
Total with taxes and fees
#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.
$862 nightly
The price is $1,017
Dec 6 - Dec 7
Total with taxes and fees
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.
$741 nightly
The price is $874
Dec 4 - Dec 5
Total with taxes and fees
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.
$791 nightly
The price is $933
Nov 24 - Nov 25
Total with taxes and fees
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
$573 nightly
The price is $676
Nov 30 - Dec 1
Total with taxes and fees
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.
$526 nightly
The price is $618
Nov 17 - Nov 18
Total with taxes and fees
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.
$386 nightly
The price is $453
Nov 16 - Nov 17
Total with taxes and fees
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
$1,067 nightly
The price is $1,266
Dec 5 - Dec 6
Total with taxes and fees
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.
$430 nightly
The price is $503
Dec 1 - Dec 2
Total with taxes and fees
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)
"Perfect!"
United States
Nick F.
$430 nightly
The price is $503
Nov 30 - Dec 1
Total with taxes and fees
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, (42 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
$475 nightly
The price is $564
Nov 15 - Nov 16
Total with taxes and fees
Signature Residences at Maui Banyan
A lush garden with a small waterfall, palm trees, and a building in the background.

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.
$829 nightly
The price is $974
Nov 15 - Nov 16
Total with taxes and fees
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.
$565 nightly
The price is $663
Nov 22 - Nov 23
Total with taxes and fees
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.
$286 nightly
The price is $336
Nov 28 - Nov 29
Total with taxes and fees
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.
$982 nightly
The price is $1,160
Nov 11 - Nov 12
Total with taxes and fees
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.
$487 nightly
The price is $574
Nov 11 - Nov 12
Total with taxes and fees
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

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

10/10 Excellent
"Please don’t force me to make a review."
Ronald 7-night trip
Posted 14 hours ago
Fairmont Kea Lani Maui

Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena vacation rentals

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

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Wailea-Makena vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wailea-Makena in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $343 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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