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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Our top choices for Wailea-Makena holiday rentals

1. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (977 reviews)
"The property was very welcoming and respectful. Love the swimming pool . We went in it every day. We meet a lot of people who has timeshares and respect their surroundings. Mahalo 🌺"
United States
Lisa
The price is NZ$598
includes taxes & fees
29 Oct - 30 Oct
Aston Maui Hill

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
The price is NZ$2,043
includes taxes & fees
30 Sept - 1 Oct
Grand Champions by KBM

3. 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.
The price is NZ$1,109
includes taxes & fees
19 Oct - 20 Oct
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

4. 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.
The price is NZ$655
includes taxes & fees
7 Oct - 8 Oct
Romantic 1 BR Condo with King Tempurpedic

5. 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.
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

6. 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.
The price is NZ$1,155
includes taxes & fees
2 Oct - 3 Oct
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

7. 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 NZ$902
includes taxes & fees
22 Oct - 23 Oct
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

8. Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM

Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM
Wailea
9.6 out of 10, Exceptional, (23 reviews)
"Super cute, spacious and well appointed condo in a great location. Host was very accessible and responsive. Would definitely stay here again!!"
United States
Chelsea H.
The price is NZ$3,709
includes taxes & fees
20 Oct - 21 Oct
Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM

9. 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
The price is NZ$924
includes taxes & fees
30 Sept - 1 Oct
Signature Residences at Maui Banyan

10. 180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
9.8 out of 10, Exceptional, (7 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is NZ$1,190
includes taxes & fees
1 Oct - 2 Oct
180 Degree Ocean View in Wailea! WE204

11. #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 NZ$1,048
includes taxes & fees
10 Oct - 11 Oct
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

12. Wailea Beach Villas Resort by KBM

Wailea Beach Villas Resort by KBM
4.0 star property
Wailea
The price is NZ$8,779
includes taxes & fees
5 Oct - 6 Oct
Wailea Beach Villas Resort by KBM

13. 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 NZ$927
includes taxes & fees
9 Oct - 10 Oct
DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

14. 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.
The price is NZ$794
includes taxes & fees
1 Oct - 2 Oct
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

15. 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.
The price is NZ$1,493
includes taxes & fees
3 Oct - 4 Oct
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views

16. 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.
The price is NZ$1,191
includes taxes & fees
1 Oct - 2 Oct
Romantic, Luxury, Sensual Retreat - Couples Only

17. 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.
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

18. Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss

Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss
South Kihei
10.0 out of 10, Exceptional, (141 reviews)
"The view alone was worth the price of admission. The condo, was incidentally, well kept; well stocked; and very comfortable. In a nutshell; if you come to Maui; I would recommend this place. "
United States
Sono J.
The price is NZ$2,084
includes taxes & fees
1 Oct - 2 Oct
Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss

19. 207 - Lovely Oceanfront One Bedroom Unit!

207 - Lovely Oceanfront One Bedroom Unit!
South Kihei
9.6 out of 10, Exceptional, (61 reviews)
"beautiful view of the ocean communication with the owner was prompt and helpful. we enjoyed our stay. "
United States
Diana E.
207 - Lovely Oceanfront One Bedroom Unit!

20. Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
South Kihei
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful property with an unreal view. "
Canada
Peter M.
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
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

Find out more about Wailea-Makena

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wailea-Makena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wailea-Makena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wailea-Makena. Seeing all the best attractions is bound to make you fall in love with Wailea-Makena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wailea-Makena short-term rentals, that won’t be hard to do.

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