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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 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, (998 reviews)
"Great experience and great location"
United States
Miguel
$251 nightly
The price is $298
Nov 15 - Nov 16
Total with taxes and fees
Aston Maui Hill
A resort pool area with a view of the ocean and a golf course in the background.

2. Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 245USD 11-5 thru 11-23 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.
$526 nightly
The price is $616
Nov 15 - Nov 16
Total with taxes and fees
Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
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.
$566 nightly
The price is $662
Oct 22 - Oct 23
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
An outdoor patio with a grill, seating, and a view of the ocean.

4. 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)
"Amazing sunsets, good privacy, a smaller quiet pool nearby, kitchen is well equipped."
United States
Petr K.
$474 nightly
The price is $554
Oct 18 - Oct 19
Total with taxes and fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
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, (64 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 24 - Oct 25
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.

6. #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 21 - Oct 22
Total with taxes and fees
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A resort with a swimming pool, palm trees, and a view of the ocean.

7. Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais

Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais
3.5 star property
Wailea
10.0 out of 10, Exceptional, (1 review)
"Perfect. This is exactly what I was looking for. Ultra quiet, beautiful, close to everything on the Wailea side. Incredible location. We had an issue with our smoke detector and they fixed it right away. Very great. We have 2 teenage daughters and we have visited Maui a few times. This place is great, and an awesome value."
United States
Joshua
$727 nightly
The price is $863
Nov 1 - Nov 2
Total with taxes and fees
Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais
A beach with palm trees and a clear sky.

8. 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.
$540 nightly
The price is $633
Oct 18 - Oct 19
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

9. 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.
$408 nightly
The price is $478
Oct 23 - Oct 24
Total with taxes and fees
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A beach with a sunset, palm trees, and rocky outcrops.

10. 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.
$582 nightly
The price is $681
Oct 20 - Oct 21
Total with taxes and fees
Romantic, Luxury, Sensual Retreat - Couples Only
A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

11. 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
$821 nightly
The price is $975
Nov 2 - Nov 3
Total with taxes and fees
Grand Champions by KBM
A resort with a central pool, palm trees, and a well-maintained lawn.

12. 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.
$542 nightly
The price is $635
Oct 19 - Oct 20
Total with taxes and fees
Romantic, Luxury Maui Getaway with Ocean View - Couples Only
A poolside area with lounge chairs and umbrellas, surrounded by palm trees and a clear view of the ocean.

13. Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Fall $199/nt!

Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Fall $199/nt!
Wailea
9.8 out of 10, Exceptional, (32 reviews)
"Thank for a wonderful stay! We love Ekahi, and this unit is absolutely fantastic! Easy walk to the pool and the beach, and a BBQ pavilion is just down the hill. Morning coffee on the lanai is the best!Thanks again for a great stay, and for accommodating us on such short notice!"
United States
Bill R.
$1,023 nightly
The price is $1,196
Nov 2 - Nov 3
Total with taxes and fees
Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Fall $199/nt!
A spacious living area with a glass table, wooden chairs, a sofa, and a view of the ocean through large windows.

14. 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, (74 reviews)
"We had the best stay! The place was lovely and in the perfect location!"
United States
Bailey G.
$795 nightly
The price is $930
Oct 28 - Oct 29
Total with taxes and fees
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
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 modern kitchen with a dining area, a ceiling fan, and a wall art piece.

16. 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.
$358 nightly
The price is $418
Oct 28 - Oct 29
Total with taxes and fees
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A swimming pool with a curved design, surrounded by palm trees and a golf course.

17. 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.
$854 nightly
The price is $1,000
Oct 20 - Oct 21
Total with taxes and fees
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A modern living room with a sofa, coffee table, and dining area.

18. 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.
$356 nightly
The price is $416
Oct 20 - Oct 21
Total with taxes and fees
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

19. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
Wailea
9.6 out of 10, Exceptional, (73 reviews)
"A fantastic place to stay! You can easily walk to shops, restaurants, and the golf course. Plus, the ocean view is amazing. "
United States
lily v.
$473 nightly
The price is $553
Oct 20 - Oct 21
Total with taxes and fees
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
A pool area with palm trees, lounge chairs, and a view of the ocean.

20. 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.
$960 nightly
The price is $1,124
Oct 24 - Oct 25
Total with taxes and fees
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
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

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"The location is great because it shares the same beach as the Grand Wailea and the Four Seasons and you can go to restaurants at all 3 resorts and the Shops at Wailea as well. Beautiful property and very attentive staff. Lunch and drinks are brought to you by the pool and we got very spoiled to that. :)"
Troy 5-night trip
Posted 3 hours ago
Wailea Beach Resort - Marriott, 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.

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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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 $298 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

At Expedia, we put the best Wailea-Makena vacation 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 vacation.

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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