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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Wailea-Makena vacation rentals

A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

1. 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.
$322 nightly
The price is $376
Oct 28 - Oct 29
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.

2. 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.
$355 nightly
The price is $415
Oct 23 - Oct 24
Total with taxes and fees
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A resort with a swimming pool, palm trees, and ocean views.

3. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (999 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
$242 nightly
The price is $287
Nov 20 - Nov 21
Total with taxes and fees
Aston Maui Hill
A red surfboard-shaped sign with 'Hana 6 Miles' and a flower symbol, surrounded by plants and a parked vehicle.

4. 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.
$360 nightly
The price is $420
Nov 9 - Nov 10
Total with taxes and fees
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
A beach with clear turquoise water, sandy shore, and palm trees.

5. 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.
$560 nightly
The price is $656
Oct 22 - Oct 23
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

6. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (40 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
$528 nightly
The price is $627
Oct 22 - Oct 23
Total with taxes and fees
Signature Residences at Maui Banyan
A resort pool area with a view of the ocean and a golf course in the background.

7. Deal 249USD 11-7 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 249USD 11-7 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.
$526 nightly
The price is $616
Nov 15 - Nov 16
Total with taxes and fees
Deal 249USD 11-7 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
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.
$536 nightly
The price is $630
Oct 29 - Oct 30
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

9. 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.
$476 nightly
The price is $557
Oct 31 - Nov 1
Total with taxes and fees
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
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 22 - Oct 23
Total with taxes and fees
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A balcony with a view of a sunset over palm trees and a row of modern buildings.

11. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"Great location and value!"
United States
Christopher
$297 nightly
The price is $347
Oct 23 - Oct 24
Total with taxes and fees
Beautiful, Renovated, Hale Kamaole 159
A pathway leading to a beach with dense green foliage on either side.

12. #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
9.6 out of 10, Exceptional, (98 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 22 - Oct 23
Total with taxes and fees
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

13. 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
$517 nightly
The price is $614
Oct 22 - Oct 23
Total with taxes and fees
The Residences at Kamaole Sands Resort
A modern bathroom with a glass shower enclosure, a white toilet, a black granite sink, and a wooden vanity.

14. 312 - Fantastic remodeled oceanfront with great ocean view and A/C!

312 - Fantastic remodeled oceanfront with great ocean view and A/C!
South Kihei
9.8 out of 10, Exceptional, (95 reviews)
"Wonderful spot and great working with Rosie's Reservations!"
United States
Greg S.
$497 nightly
The price is $582
Oct 23 - Oct 24
Total with taxes and fees
312 - Fantastic remodeled oceanfront with great ocean view and A/C!
A resort with a swimming pool, palm trees, and a view of the ocean.

15. 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
$786 nightly
The price is $934
Nov 1 - Nov 2
Total with taxes and fees
Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais
Room

16. Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem

Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem
South Kihei
9.0 out of 10, Wonderful, (2 reviews)
"Checkin was very fast, and easy to navigate. Talked with a front desk person and that was it.The location is great, only a 5-10 minute walk down to the beach and very close to downtown Kihei!"
United States
Anthony N.
$364 nightly
The price is $424
Oct 24 - Oct 25
Total with taxes and fees
Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

17. 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.
$382 nightly
The price is $447
Oct 22 - Oct 23
Total with taxes and fees
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A beach with a sunset, palm trees, and rocky outcrops.

18. 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.
$589 nightly
The price is $688
Nov 11 - Nov 12
Total with taxes and fees
Romantic, Luxury, Sensual Retreat - Couples Only
A sandy beach with footprints, a few people, and a boat.

19. 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.
$350 nightly
The price is $410
Oct 24 - Oct 25
Total with taxes and fees
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
A resort with a well-maintained garden, palm trees, and a view of the ocean.

20. Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach
South Kihei
9.8 out of 10, Exceptional, (127 reviews)
"This was a great condo. Close to the pool and parking right out your door. it was well appointed with everything a family needs for the beach and extra bed and play and pak for the little one. We will definitely be saying her again!"
United States
Jody S.
$468 nightly
The price is $547
Oct 27 - Oct 28
Total with taxes and fees
Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach
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

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

10/10 Excellent
"I loved staying here. Beautiful View from the 6th floor, beachfront location, walkable distance to the beach. The room was spacious, and clean. I do wish the fitness center was open late."
Anastacia D 4-night trip
Posted 6 hours ago
Mana Kai Maui- Official Onsite Rental

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 $287 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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