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. 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
The price is CA $99
CA $800 total
includes taxes & fees
Sep 27 - Sep 28
The Residences at Kamaole Sands Resort

2. 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 $72
CA $741 total
includes taxes & fees
Sep 29 - Sep 30
Signature Residences at Maui Banyan

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 CA $236
CA $782 total
includes taxes & fees
Sep 27 - Sep 28
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

4. 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 $212
CA $643 total
includes taxes & fees
Oct 1 - Oct 2
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

5. Beautiful Ocean View Studio!

Beautiful Ocean View Studio!
South Kihei
9.6 out of 10, Exceptional, (19 reviews)
"We loved the location and partial ocean view from the balcony. Easy walk to the beach and we had everything available that we needed for a comfortable stay. "
United States
Susan C.
The price is CA $163
CA $630 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful Ocean View Studio!

6. 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 $223
CA $531 total
includes taxes & fees
Oct 4 - Oct 5
Romantic 1 BR Condo with King Tempurpedic

7. 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 $128
CA $594 total
includes taxes & fees
Sep 27 - Sep 28
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

8. 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 CA $276
CA $973 total
includes taxes & fees
Oct 1 - Oct 2
180 Degree Ocean View in Wailea! WE204

9. #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 $147
CA $790 total
includes taxes & fees
Sep 27 - Sep 28
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

10. 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 $215
CA $852 total
includes taxes & fees
Oct 3 - Oct 4
Wailea Luxury Retreat | Walk to Beach & Shops

11. 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, (61 reviews)
"great place for walking to the beach"
United States
Kim & Tom C.
The price is CA $204
CA $584 total
includes taxes & fees
Oct 1 - Oct 2
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

12. Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C

Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
South Kihei
9.8 out of 10, Exceptional, (133 reviews)
"We had a great stay at the condo. The location was perfect. The condo was spotless and the amenities very useful, especially all the beach equipment. And thanks for the snacks and candy that were there when we arrived."
United States
Bob J.
The price is CA $190
CA $584 total
includes taxes & fees
Oct 1 - Oct 2
Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C

13. One Bedroom Ocean View

One Bedroom Ocean View
South Kihei
10.0 out of 10, Exceptional, (4 reviews)
"Liked location. "
United States
Patricia
The price is CA $154
CA $617 total
includes taxes & fees
Sep 28 - Sep 29
One Bedroom Ocean View

14. King Bed, Ocean View, AC, Pool, Walk to Beach

King Bed, Ocean View, AC, Pool, Walk to Beach
South Kihei
9.6 out of 10, Exceptional, (57 reviews)
"Full Kitchen, beach chair and cooler "
United States
Candace B.
The price is CA $134
CA $614 total
includes taxes & fees
Sep 28 - Sep 29
King Bed, Ocean View, AC, Pool, Walk to Beach

15. Partial Ocean View, Pool, WiFi, Walk to Beach, ACs

Partial Ocean View, Pool, WiFi, Walk to Beach, ACs
South Kihei
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful and excellent location"
United States
Michael K.
The price is CA $127
CA $613 total
includes taxes & fees
Sep 28 - Sep 29
Partial Ocean View, Pool, WiFi, Walk to Beach, ACs

16. 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 CA $416
CA $494 total
includes taxes & fees
Oct 26 - Oct 27
Aston Maui Hill

17. Across from Kamaole 2 Beach, concrete building, well maintained.

Across from Kamaole 2 Beach, concrete building, well maintained.
South Kihei
10.0 out of 10, Exceptional, (167 reviews)
"Great location!"
United States
Tyler B.
The price is CA $190
CA $526 total
includes taxes & fees
Sep 27 - Sep 28
Across from Kamaole 2 Beach, concrete building, well maintained.

18. 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, (186 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 $274
CA $766 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

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, (95 reviews)
"The condo was great very comfortable nice and clean also in a very good location"
United States
Holly P.
The price is CA $133
CA $604 total
includes taxes & fees
Sep 27 - Sep 28
5th Floor Oceanview Retreat Steps from the Beach + new split AC !

20. COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
Wailea
9.8 out of 10, Exceptional, (129 reviews)
"Wonderful, modern, great location condo!"
United States
Jaclyn G.
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
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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