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

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Our top choices for Wailea-Makena holiday rentals

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 £274
includes taxes & fees
19 Oct - 20 Oct
Romantic 1 BR Condo with King Tempurpedic

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 £332
includes taxes & fees
28 Oct - 29 Oct
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

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 £424
includes taxes & fees
17 Oct - 18 Oct
DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

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.
The price is £469
includes taxes & fees
23 Oct - 24 Oct
Wailea Luxury Retreat | Walk to Beach & Shops

5. 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
The price is £396
includes taxes & fees
15 Oct - 16 Oct
Signature Residences at Maui Banyan

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 £367
includes taxes & fees
22 Oct - 23 Oct
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

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 £364
includes taxes & fees
9 Nov - 10 Nov
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

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)
"The condo was spotless and well appointed. We hope to stay there again."
United States
Ralph N.
The price is £421
includes taxes & fees
16 Oct - 17 Oct
Ekahi 27A: Priceless Ocean View from a Private Lanai

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 £466
includes taxes & fees
13 Oct - 14 Oct
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

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 £464
includes taxes & fees
12 Oct - 13 Oct
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

11. Totally renovated, closest to the beach!

Totally renovated, closest to the beach!
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 £443
includes taxes & fees
20 Oct - 21 Oct
Totally renovated, closest to the beach!

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 £418
includes taxes & fees
21 Oct - 22 Oct
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

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, (14 reviews)
"Loved the direct access to beach. Pools were amazingly clean. Awesome sunset. Quiet property."
United States
Caroline W.
Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!

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

15. 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.
The price is £273
includes taxes & fees
23 Oct - 24 Oct
Beautiful, Renovated, Hale Kamaole 159

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 £324
includes taxes & fees
13 Oct - 14 Oct
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

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 £756
includes taxes & fees
20 Oct - 21 Oct
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

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 £416
includes taxes & fees
16 Oct - 17 Oct
206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!

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 £492
includes taxes & fees
12 Oct - 13 Oct
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

20. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (991 reviews)
"Way more than what we expected.. clean, well kept, extremely spacious and centrally located to shops, beaches and restaurants. Loved everything about the property"
United States
Michael
The price is £228
includes taxes & fees
11 Nov - 12 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

Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wailea-Makena holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wailea-Makena holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wailea-Makena holiday rentals we have selected for you start as low as £228 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

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

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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