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

Wailea-Makena Holiday Rentals

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Our top choices for Wailea-Makena holiday rentals

1. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (42 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 NZ$1,114
includes taxes & fees
1 Dec - 2 Dec
Signature Residences at Maui Banyan

2. Cozy, Well-Furnished Studio

Cozy, Well-Furnished Studio
Wailea
9.0 out of 10, Wonderful, (71 reviews)
"Wonderful bed, slept very well. Large bathroom with plenty of counter space. A tiny tiny kitchenette. Had not realized that we’d have to stand on someone else’s balcony in front of their sliding glass doors, in order to do laundry, or that laundry could only be done in daylight hours. (It’s much preferable for us, while on vacation, to do laundry at night.) Well-stocked room. Would stay again."
United States
Lisa Q.
The price is NZ$610
includes taxes & fees
28 Nov - 29 Nov
Cozy, Well-Furnished Studio

3. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (65 reviews)
"Great property, very clean. We had a wonderful stay"
United States
Linh H.
The price is NZ$650
includes taxes & fees
20 Nov - 21 Nov
Romantic 1 BR Condo with King Tempurpedic

4. 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, (82 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 NZ$929
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

5. 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 NZ$929
includes taxes & fees
1 Dec - 2 Dec
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

6. StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
Wailea
9.8 out of 10, Exceptional, (53 reviews)
"Perfect!"
United States
Nick F.
The price is NZ$929
includes taxes & fees
30 Nov - 1 Dec
StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

7. #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 NZ$1,098
includes taxes & fees
18 Nov - 19 Nov
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

8. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (1,004 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is NZ$573
includes taxes & fees
14 Dec - 15 Dec
Aston Maui Hill

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, (166 reviews)
"Everything was amazing, I enjoyed all the amenities the room had to offer. Will definitely book again in the future."
United States
Rojelio G.
The price is NZ$1,185
includes taxes & fees
21 Nov - 22 Nov
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

10. #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, (99 reviews)
"Kitchen was fully equipped. Condo was very clean and host was promt with replys. Loved our stay "
Canada
Lori D.
The price is NZ$942
includes taxes & fees
1 Dec - 2 Dec
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

11. Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Wailea
10.0 out of 10, Exceptional, (77 reviews)
"Great place to stay for your vacation!"
United States
Nick D.
The price is NZ$1,609
includes taxes & fees
4 Dec - 5 Dec
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

12. 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 NZ$1,037
includes taxes & fees
15 Nov - 16 Nov
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

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. Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach
South Kihei
9.6 out of 10, Exceptional, (129 reviews)
"This was a great condo. Close to the pool and parking right out your door. it was well appointed with everything a family needs for the beach and extra bed and play and pak for the little one. We will definitely be saying her again!"
United States
Jody S.
The price is NZ$989
includes taxes & fees
12 Dec - 13 Dec
Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

15. Luxury Condo on Wailea Blue Golf Course

Luxury Condo on Wailea Blue Golf Course
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"Very nice condo. Accommodated everything we needed for a wonderful vacation."
United States
Bryce
The price is NZ$1,235
includes taxes & fees
30 Nov - 1 Dec
Luxury Condo on Wailea Blue Golf Course

16. Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
South Kihei
10.0 out of 10, Exceptional, (177 reviews)
"Great location in the heart of Kihei. Easy parking. Well equipped condo with view of the ocean. Owners very responsive to questions."
United States
Jo
The price is NZ$689
includes taxes & fees
17 Nov - 18 Nov
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

17. 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 NZ$638
includes taxes & fees
19 Nov - 20 Nov
Beautiful, Renovated, Hale Kamaole 159

18. Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV

Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV
South Kihei
9.6 out of 10, Exceptional, (108 reviews)
"Great spot!! "
United States
Terris S.
The price is NZ$1,268
includes taxes & fees
12 Dec - 13 Dec
Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV

19. 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 NZ$1,061
includes taxes & fees
27 Nov - 28 Nov
Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

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 NZ$1,147
includes taxes & fees
17 Nov - 18 Nov
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wailea-Makena holiday 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. 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 holiday just got upgraded.

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

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