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

Wailea-Makena Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Wailea-Makena vacation 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 CA $216
CA $527 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $214
CA $648 total
includes taxes & fees
Oct 28 - Oct 29
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

3. Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 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 $307
CA $813 total
includes taxes & fees
Oct 17 - Oct 18
Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

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

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 CA $72
CA $747 total
includes taxes & fees
Oct 15 - Oct 16
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 CA $279
CA $707 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $250
CA $698 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $235
CA $790 total
includes taxes & fees
Oct 16 - Oct 17
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 CA $312
CA $894 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $334
CA $871 total
includes taxes & fees
Oct 13 - Oct 14
#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 CA $255
CA $837 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $149
CA $799 total
includes taxes & fees
Oct 21 - Oct 22
#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.
The price is CA $318
CA $1,377 total
includes taxes & fees
Oct 14 - Oct 15
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.
The price is CA $276
CA $798 total
includes taxes & fees
Oct 20 - Oct 21
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)
"Great location and value!"
United States
Christopher
The price is CA $178
CA $525 total
includes taxes & fees
Oct 23 - Oct 24
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 CA $129
CA $599 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $577
CA $1,439 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $193
CA $779 total
includes taxes & fees
Oct 16 - Oct 17
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 CA $428
CA $939 total
includes taxes & fees
Oct 13 - Oct 14
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, (992 reviews)
"Nice location. Very hospitable and Kind staff. Would stay here again"
United States
Kifaya
The price is CA $363
CA $431 total
includes taxes & fees
Nov 11 - Nov 12
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia