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

Wailea-Makena Vacation Rentals

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, (986 reviews)
"Worth the price"
United States
ADITYA
$276 nightly
The price is $328
Nov 5 - Nov 6
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
$825 nightly
The price is $979
Oct 7 - Oct 8
Total with taxes and fees
Grand Champions by KBM
A beach with clear turquoise water, sandy shore, and palm trees.

3. Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Wailea
10.0 out of 10, Exceptional, (61 reviews)
"Location is excellent."
United States
Amund N.
$491 nightly
The price is $575
Oct 7 - Oct 8
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
A beach with palm trees and a clear sky.

4. 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)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
$494 nightly
The price is $579
Oct 7 - Oct 8
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.

5. 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.
$319 nightly
The price is $373
Oct 15 - Oct 16
Total with taxes and fees
Romantic 1 BR Condo with King Tempurpedic
A resort pool area with a view of the ocean and a golf course in the background.

6. Deal 275USD 10-31 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 275USD 10-31 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
Wailea
9.8 out of 10, Exceptional, (187 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.
$482 nightly
The price is $564
Oct 9 - Oct 10
Total with taxes and fees
Deal 275USD 10-31 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
A swimming pool with a curved design, surrounded by palm trees and a golf course.

7. 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)
"Nice location and resort. Lots of clear instructions in advance from the host and inside the unit. Comfortable bed!"
United States
Richard F.
$863 nightly
The price is $1,009
Oct 20 - Oct 21
Total with taxes and fees
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

8. 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
$447 nightly
The price is $531
Oct 12 - Oct 13
Total with taxes and fees
Signature Residences at Maui Banyan
A tropical garden with a waterfall, palm trees, and a variety of lush greenery.

9. 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.
$535 nightly
The price is $641
Oct 10 - Oct 11
Total with taxes and fees
Wailea Luxury Retreat | Walk to Beach & Shops
A wooden table with a bottle of wine and two glasses on a balcony overlooking a lush garden and the ocean.

10. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Wailea
9.8 out of 10, Exceptional, (193 reviews)
"Amazing view, good size spaces nice proximity to the shops in Wailea. Overall great stay."
United States
Scott M.
$525 nightly
The price is $614
Oct 10 - Oct 11
Total with taxes and fees
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A modern kitchen with a dining area, a ceiling fan, and a wall art piece.

11. 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, (39 reviews)
"Location location location! Just 1 block from the shops and Wailea beach…can’t beat that! "
United States
david k.
$387 nightly
The price is $452
Oct 28 - Oct 29
Total with taxes and fees
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A resort pool area with a hot tub, lounge chairs, and palm trees.

12. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
$1,401 nightly
The price is $1,663
Oct 12 - Oct 13
Total with taxes and fees
Villa, Garden View, 2-bedroom
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

13. 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, (81 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.
$419 nightly
The price is $491
Oct 22 - Oct 23
Total with taxes and fees
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A pool area with palm trees, lounge chairs, and a view of the ocean.

14. 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.
$953 nightly
The price is $1,117
Oct 24 - Oct 25
Total with taxes and fees
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
A resort with a swimming pool, palm trees, and hanging decorative spheres.

15. 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, (90 reviews)
"Perfect spot and location for our spring break getaway. This unit has lots of amenities available just steps away. "
United States
Corey R.
$879 nightly
The price is $1,028
Oct 29 - Oct 30
Total with taxes and fees
Wailea Ekahi 29C, Ocean View, Steps away from the pool
A coastal view with clear turquoise waters, rocky shoreline, and distant buildings.

16. Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112

Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
Wailea
9.2 out of 10, Wonderful, (9 reviews)
"The home was comfortable and clean! "
United States
Candace C.
$710 nightly
The price is $833
Oct 9 - Oct 10
Total with taxes and fees
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
A beach with palm trees, a clear blue sky, and a view of the ocean.

17. Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views

Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views
Wailea
9.8 out of 10, Exceptional, (63 reviews)
"The condo was exactly as listed and Heather was very accommodating with answering our questions before and during the stay. The location is very walkable to several beaches and shops. We would definitely stay here again. "
United States
Amy P.
$711 nightly
The price is $835
Oct 7 - Oct 8
Total with taxes and fees
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views
An outdoor patio with a grill, seating, and a view of the ocean.

18. 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, (55 reviews)
"Ocean view! We loved it! We even slept great…Winning!!"
United States
Isabel P.
$474 nightly
The price is $554
Oct 7 - Oct 8
Total with taxes and fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

19. 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
$492 nightly
The price is $584
Oct 7 - Oct 8
Total with taxes and fees
The Residences at Kamaole Sands Resort
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a balcony with a view of greenery.

20. 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.
$547 nightly
The price is $640
Oct 19 - Oct 20
Total with taxes and fees
Romantic, Luxury Maui Getaway with Ocean View - Couples Only
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
"The staff were amazing, evening room service was excellent surprise"
Mohammed 3-night trip
Posted 1 hour 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 $328 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

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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 vacation.

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