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

Wailea-Makena Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Wailea-Makena holiday 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.
The price is HK$1,236
HK$2,928 total
includes taxes & fees
22 Oct - 23 Oct
Romantic 1 BR Condo with King Tempurpedic
A modern kitchen with a dining area, a ceiling fan, and a wall art piece.

2. 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.
The price is HK$981
HK$3,280 total
includes taxes & fees
28 Oct - 29 Oct
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A resort pool area with a view of the ocean and a golf course in the background.

3. DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose
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.
The price is HK$1,519
HK$4,204 total
includes taxes & fees
17 Oct - 18 Oct
DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose
A tropical garden with a waterfall, palm trees, and a variety of lush greenery.

4. 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.
Wailea Luxury Retreat | Walk to Beach & Shops
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

5. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (41 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
The price is HK$249
HK$3,792 total
includes taxes & fees
16 Oct - 17 Oct
Signature Residences at Maui Banyan
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

6. 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.
The price is HK$1,326
HK$3,542 total
includes taxes & fees
16 Oct - 17 Oct
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A clear beach with visible pebbles and a mountain in the distance.

7. 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.
The price is HK$981
HK$3,263 total
includes taxes & fees
20 Oct - 21 Oct
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
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, (55 reviews)
"Amazing sunsets, good privacy, a smaller quiet pool nearby, kitchen is well equipped."
United States
Petr K.
The price is HK$1,295
HK$4,351 total
includes taxes & fees
16 Oct - 17 Oct
Ekahi 27A: Priceless Ocean View from a Private Lanai
A beach with palm trees and a clear sky.

9. 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.
The price is HK$1,797
HK$4,964 total
includes taxes & fees
18 Oct - 19 Oct
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
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.
The price is HK$1,836
HK$4,819 total
includes taxes & fees
21 Oct - 22 Oct
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A grill with a stone base, a view of the ocean, and palm trees.

11. Totally renovated, closest to the beach! Oct. 199!

Totally renovated, closest to the beach! Oct. 199!
Wailea
9.8 out of 10, Exceptional, (232 reviews)
"Property is beautiful, super close to beach and pools. Has everything needed for a relaxing vacation. Host was wonderful to work with."
United States
Sandy S.
The price is HK$1,406
HK$4,567 total
includes taxes & fees
20 Oct - 21 Oct
Totally renovated, closest to the beach! Oct. 199!
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.
The price is HK$818
HK$4,399 total
includes taxes & fees
21 Oct - 22 Oct
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A resort with a pool, palm trees, and a view of the ocean.

13. 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, (15 reviews)
"Loved the direct access to beach. Pools were amazingly clean. Awesome sunset. Quiet property."
United States
Caroline W.
The price is HK$3,296
HK$9,957 total
includes taxes & fees
26 Oct - 27 Oct
Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!
A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

14. 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.
The price is HK$1,519
HK$4,343 total
includes taxes & fees
20 Oct - 21 Oct
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
A balcony with a view of a sunset over palm trees and a row of modern buildings.

15. 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
The price is HK$883
HK$2,733 total
includes taxes & fees
24 Oct - 25 Oct
Beautiful, Renovated, Hale Kamaole 159
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

16. 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.
The price is HK$932
HK$3,605 total
includes taxes & fees
24 Oct - 25 Oct
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
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.
The price is HK$3,178
HK$7,847 total
includes taxes & fees
20 Oct - 21 Oct
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A balcony with a glass table, chairs, and a view of the ocean and palm trees.

18. 206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!

206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
South Kihei
9.8 out of 10, Exceptional, (64 reviews)
"The Surfside is a spectacular property. You cannot go wrong. The property owner/management company was very responsive and organized."
United States
Slate S.
The price is HK$1,061
HK$4,307 total
includes taxes & fees
16 Oct - 17 Oct
206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
A beach with clear turquoise water, sandy shore, and palm trees.

19. 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.
The price is HK$2,354
HK$5,179 total
includes taxes & fees
16 Oct - 17 Oct
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
A resort with a swimming pool, palm trees, and ocean views.

20. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (996 reviews)
"Nice location. Very hospitable and Kind staff. Would stay here again"
United States
Kifaya
The price is HK$2,290
HK$2,718 total
includes taxes & fees
15 Nov - 16 Nov
Aston Maui Hill
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

8/10 Good
"Older property with beautiful views and location, but room furniture needs updating in a desperate way. The views and location do not match the furnishings of what is offered. Staff is amazing, so friendly and treat you like family. Had the most memorable trip ever, everyday melted my stress away. Thank you for your kindness and flexibility so very much deserved."
JoAnn R 3-night trip
Posted 14 hours ago
Mana Kai Maui- Official Onsite Rental

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