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

Wailea-Makena Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Wailea-Makena vacation rentals

A tropical garden with a waterfall, palm trees, and a variety of lush greenery.

1. 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.
$513 nightly
The price is $615
Oct 4 - Oct 5
Total with taxes and fees
Wailea Luxury Retreat | Walk to Beach & Shops
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

2. 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 10 - Oct 11
Total with taxes and fees
Romantic 1 BR Condo with King Tempurpedic
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

3. 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.
$422 nightly
The price is $494
Oct 22 - Oct 23
Total with taxes and fees
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A resort pool area with a view of the ocean and a golf course in the background.

4. Gorgeous Gem Walk to Beach and Sunset View Pool FULL AC 2026 77" & 55"OLED TV's

Gorgeous Gem Walk to Beach and Sunset View Pool FULL AC 2026 77" & 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.
$457 nightly
The price is $536
Oct 9 - Oct 10
Total with taxes and fees
Gorgeous Gem Walk to Beach and Sunset View Pool FULL AC 2026 77" & 55"OLED TV's
A modern kitchen with a dining area, a ceiling fan, and a wall art piece.

5. 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.
$413 nightly
The price is $482
Oct 28 - Oct 29
Total with taxes and fees
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A pathway leading to a beach with dense green foliage on either side.

6. #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.
$479 nightly
The price is $561
Oct 4 - Oct 5
Total with taxes and fees
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A wooden table with a bottle of wine and two glasses on a balcony overlooking a lush garden and the ocean.

7. #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 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, (164 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
$529 nightly
The price is $620
Oct 5 - Oct 6
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A balcony with a view of a sunset over palm trees and a row of modern buildings.

9. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"I’ve stayed at several units in the same complex and this one was one of the best. Nicely appointed and a great view from the lanai. The bed was very comfy and the AC worked great. It’s so nice to be able to walk across the street to such a nice beach, we even saw a turtle in the water."
United States
Daniel L.
$313 nightly
The price is $366
Oct 23 - Oct 24
Total with taxes and fees
Beautiful, Renovated, Hale Kamaole 159
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

10. 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
$493 nightly
The price is $585
Oct 5 - Oct 6
Total with taxes and fees
Signature Residences at Maui Banyan
A kitchen with white cabinets, a marble countertop, a kettle, and a vase with flowers.

11. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
Wailea
10.0 out of 10, Exceptional, (44 reviews)
"Great condo! "
Canada
Marcie M.
$403 nightly
The price is $472
Oct 11 - Oct 12
Total with taxes and fees
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
An outdoor patio with a grill, seating, and a view of the ocean.

12. 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 6 - Oct 7
Total with taxes and fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
A clear blue pool surrounded by palm trees and a building with balconies.

13. Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View

Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View
Wailea
$544 nightly
The price is $638
Oct 29 - Oct 30
Total with taxes and fees
Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View
A resort with a pool, palm trees, and a view of the ocean.

14. Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!

Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!
Wailea
10.0 out of 10, Exceptional, (14 reviews)
"Loved the direct access to beach. Pools were amazingly clean. Awesome sunset. Quiet property."
United States
Caroline W.
$817 nightly
The price is $956
Oct 4 - Oct 5
Total with taxes and fees
Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

15. 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.
$356 nightly
The price is $416
Oct 4 - Oct 5
Total with taxes and fees
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A beach with clear turquoise water, sandy shore, and palm trees.

16. 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, (60 reviews)
"Location is excellent."
United States
Amund N.
$492 nightly
The price is $576
Oct 4 - Oct 5
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

17. 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, (72 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 4 - Oct 5
Total with taxes and fees
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
A clear swimming pool surrounded by lush greenery and palm trees.

18. Beautiful 1 Bed 2 Bath Condo at Maui Kamaole

Beautiful 1 Bed 2 Bath Condo at Maui Kamaole
South Kihei
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely exceeded my expectations the owners and staff went above and beyond to make my stay exceptional Clean condo.. comfy bed..had everything you need to be at your home away from home great poolHot tub was perfect temperature Close to the beach and all the amenities "
Canada
Jeff B.
$438 nightly
The price is $512
Oct 4 - Oct 5
Total with taxes and fees
Beautiful 1 Bed 2 Bath Condo at Maui Kamaole
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, (96 reviews)
"The condo was great very comfortable nice and clean also in a very good location"
United States
Holly P.
$356 nightly
The price is $417
Oct 4 - Oct 5
Total with taxes and fees
5th Floor Oceanview Retreat Steps from the Beach + new split AC !
A sandy beach with footprints, a few people, and a boat.

20. 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, (62 reviews)
"great place for walking to the beach"
United States
Kim & Tom C.
$349 nightly
The price is $409
Oct 4 - Oct 5
Total with taxes and fees
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
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

Aston at the Maui Banyan

Aston at the Maui Banyan

10/10 Excellent
"This was our third time at this resort. Our unit was fabulous! Clean, stocked with kitchen equipment, soap for laundry, 2 full CLEAN bathrooms and a very comfy bed. We will be back. Oh the pool is wonderful too!"
Heather 2-night trip
Posted 3 hours ago
Aston at the Maui Banyan

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 $331 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.

Explore a world of travel with Expedia