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, (1,000 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is CA $384
CA $456 total
includes taxes & fees
Nov 26 - Nov 27
Aston Maui Hill

2. 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 $212
CA $611 total
includes taxes & fees
Nov 1 - Nov 2
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

3. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (65 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 $245
CA $562 total
includes taxes & fees
Nov 20 - Nov 21
Romantic 1 BR Condo with King Tempurpedic

4. 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 $176
CA $590 total
includes taxes & fees
Nov 9 - Nov 10
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

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, (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 $162
CA $571 total
includes taxes & fees
Oct 29 - Oct 30
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

6. Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
South Kihei
9.2 out of 10, Wonderful, (19 reviews)
"The location of this unit is wonderful. Close to beach, parks, restaurants, and tennis. "
United States
Paul B.
The price is CA $373
CA $872 total
includes taxes & fees
Nov 10 - Nov 11
Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

7. 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 $67
CA $726 total
includes taxes & fees
Oct 30 - Oct 31
Signature Residences at Maui Banyan

8. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Wailea
9.8 out of 10, Exceptional, (194 reviews)
"Amazing view, good size spaces nice proximity to the shops in Wailea. Overall great stay."
United States
Scott M.
The price is CA $329
CA $854 total
includes taxes & fees
Nov 18 - Nov 19
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

9. 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 $492
CA $1,024 total
includes taxes & fees
Nov 10 - Nov 11
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

10. 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 $336
CA $918 total
includes taxes & fees
Oct 29 - Oct 30
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

11. 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 $271
CA $784 total
includes taxes & fees
Nov 1 - Nov 2
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

12. Deal 225USD 11-7 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 225USD 11-7 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 $349
CA $957 total
includes taxes & fees
Nov 15 - Nov 16
Deal 225USD 11-7 thru 11-11 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

13. #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 $175
CA $826 total
includes taxes & fees
Nov 26 - Nov 27
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

14. 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 $157
CA $917 total
includes taxes & fees
Oct 30 - Oct 31
The Residences at Kamaole Sands Resort

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 $177
CA $518 total
includes taxes & fees
Nov 12 - Nov 13
Beautiful, Renovated, Hale Kamaole 159

16. 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 $553
CA $1,344 total
includes taxes & fees
Nov 19 - Nov 20
Grand Champions by KBM

17. 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, (57 reviews)
"Amazing sunsets, good privacy, a smaller quiet pool nearby, kitchen is well equipped."
United States
Petr K.
The price is CA $349
CA $934 total
includes taxes & fees
Oct 30 - Oct 31
Ekahi 27A: Priceless Ocean View from a Private Lanai

18. Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais

Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais
3.5 star property
Wailea
10.0 out of 10, Exceptional, (1 review)
"Perfect. This is exactly what I was looking for. Ultra quiet, beautiful, close to everything on the Wailea side. Incredible location. We had an issue with our smoke detector and they fixed it right away. Very great. We have 2 teenage daughters and we have visited Maui a few times. This place is great, and an awesome value."
United States
Joshua
The price is CA $596
CA $1,371 total
includes taxes & fees
Nov 1 - Nov 2
Palms at Wailea 101 - 2BR Garden View Condo w/ A/C in Bedrooms & Spacious Lanais

19. 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 $132
CA $600 total
includes taxes & fees
Oct 29 - Oct 30
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

20. Romantic, Luxury, Sensual Retreat - Couples Only

Romantic, Luxury, Sensual Retreat - Couples Only
Wailea
10.0 out of 10, Exceptional, (209 reviews)
"Just perfect! Amazing property and amazing location!"
United States
Jessica N.
The price is CA $449
CA $967 total
includes taxes & fees
Nov 11 - Nov 12
Romantic, Luxury, Sensual Retreat - 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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