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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Our top choices for Wailea-Makena vacation rentals

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.
The price is CA $232
CA $877 total
includes taxes & fees
Oct 4 - Oct 5
Wailea Luxury Retreat | Walk to Beach & Shops

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.
The price is CA $224
CA $532 total
includes taxes & fees
Oct 9 - Oct 10
Romantic 1 BR Condo with King Tempurpedic

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.
The price is CA $279
CA $699 total
includes taxes & fees
Oct 22 - Oct 23
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

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.
The price is CA $275
CA $771 total
includes taxes & fees
Oct 9 - Oct 10
Gorgeous Gem Walk to Beach and Sunset View Pool FULL AC 2026 77" & 55"OLED TV's

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.
The price is CA $249
CA $698 total
includes taxes & fees
Oct 28 - Oct 29
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

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.
The price is CA $148
CA $797 total
includes taxes & fees
Oct 5 - Oct 6
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

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.
The price is CA $333
CA $873 total
includes taxes & fees
Oct 10 - Oct 11
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

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.
The price is CA $311
CA $892 total
includes taxes & fees
Oct 6 - Oct 7
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

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.
The price is CA $178
CA $518 total
includes taxes & fees
Oct 23 - Oct 24
Beautiful, Renovated, Hale Kamaole 159

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
The price is CA $100
CA $805 total
includes taxes & fees
Oct 5 - Oct 6
Signature Residences at Maui Banyan

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.
The price is CA $249
CA $696 total
includes taxes & fees
Oct 11 - Oct 12
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

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.
The price is CA $235
CA $789 total
includes taxes & fees
Oct 6 - Oct 7
Ekahi 27A: Priceless Ocean View from a Private Lanai

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

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.
The price is CA $317
CA $1,374 total
includes taxes & fees
Oct 14 - Oct 15
Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!

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.
The price is CA $122
CA $591 total
includes taxes & fees
Oct 5 - Oct 6
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

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.
The price is CA $341
CA $827 total
includes taxes & fees
Oct 5 - Oct 6
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

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.
The price is CA $275
CA $796 total
includes taxes & fees
Oct 31 - Nov 1
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

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.
The price is CA $166
CA $736 total
includes taxes & fees
Oct 4 - Oct 5
Beautiful 1 Bed 2 Bath Condo at Maui Kamaole

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.
The price is CA $128
CA $599 total
includes taxes & fees
Oct 5 - Oct 6
5th Floor Oceanview Retreat Steps from the Beach + new split AC !

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.
The price is CA $205
CA $587 total
includes taxes & fees
Oct 5 - Oct 6
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.
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Top Wailea-Makena Hotel Reviews

Find out more about Wailea-Makena

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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