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. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (990 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 CA $426
CA $506 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $681
CA $1,505 total
includes taxes & fees
Oct 11 - Oct 12
Grand Champions by KBM

3. 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 $348
CA $834 total
includes taxes & fees
Oct 11 - Oct 12
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

4. 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 $892 total
includes taxes & fees
Oct 13 - Oct 14
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

5. 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 $215
CA $526 total
includes taxes & fees
Oct 20 - Oct 21
Romantic 1 BR Condo with King Tempurpedic

6. Deal 275USD 10-31 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 275USD 10-31 thru 11-11 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 $306
CA $812 total
includes taxes & fees
Oct 17 - Oct 18
Deal 275USD 10-31 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

7. 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 $576
CA $1,415 total
includes taxes & fees
Oct 20 - Oct 21
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

8. 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 $93
CA $791 total
includes taxes & fees
Oct 11 - Oct 12
Signature Residences at Maui Banyan

9. 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 $332
CA $995 total
includes taxes & fees
Oct 11 - Oct 12
Wailea Luxury Retreat | Walk to Beach & Shops

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 $333
CA $869 total
includes taxes & fees
Oct 11 - Oct 12
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

11. 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 $213
CA $647 total
includes taxes & fees
Oct 28 - Oct 29
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

12. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is CA $1,314
CA $2,366 total
includes taxes & fees
Oct 12 - Oct 13
Villa, Garden View, 2-bedroom

13. 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 $705 total
includes taxes & fees
Oct 22 - Oct 23
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

14. 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.
The price is CA $711
CA $1,618 total
includes taxes & fees
Oct 24 - Oct 25
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

15. Wailea Ekahi 29C, Ocean View, Steps away from the pool

Wailea Ekahi 29C, Ocean View, Steps away from the pool
Wailea
10.0 out of 10, Exceptional, (90 reviews)
"Perfect spot and location for our spring break getaway. This unit has lots of amenities available just steps away. "
United States
Corey R.
The price is CA $710
CA $1,462 total
includes taxes & fees
Oct 29 - Oct 30
Wailea Ekahi 29C, Ocean View, Steps away from the pool

16. Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112

Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
Wailea
9.2 out of 10, Wonderful, (9 reviews)
"The home was comfortable and clean! "
United States
Candace C.
The price is CA $444
CA $1,211 total
includes taxes & fees
Oct 12 - Oct 13
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112

17. 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 CA $506
CA $1,294 total
includes taxes & fees
Oct 20 - Oct 21
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views

18. 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 17 - Oct 18
Ekahi 27A: Priceless Ocean View from a Private Lanai

19. 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 $133
CA $876 total
includes taxes & fees
Oct 13 - Oct 14
The Residences at Kamaole Sands Resort

20. Romantic, Luxury Maui Getaway with Ocean View - Couples Only

Romantic, Luxury Maui Getaway with Ocean View - Couples Only
Wailea
10.0 out of 10, Exceptional, (22 reviews)
"Just a wonderful stay. Everything is just right and the property is beautiful. "
United States
Roger B.
The price is CA $404
CA $903 total
includes taxes & fees
Oct 20 - Oct 21
Romantic, Luxury Maui Getaway with Ocean View - Couples Only
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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