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, (971 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is CA $399
CA $474 total
includes taxes & fees
Oct 20 - Oct 21
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 $401
CA $1,161 total
includes taxes & fees
Sep 29 - Sep 30
Grand Champions by KBM

3. 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 $558
CA $1,400 total
includes taxes & fees
Sep 21 - Sep 22
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

4. 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 $220
CA $498 total
includes taxes & fees
Sep 29 - Sep 30
Romantic 1 BR Condo with King Tempurpedic

5. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Wailea
9.8 out of 10, Exceptional, (192 reviews)
"Amazing view, good size spaces nice proximity to the shops in Wailea. Overall great stay."
United States
Scott M.
The price is CA $327
CA $854 total
includes taxes & fees
Sep 20 - Sep 21
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

6. 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, (60 reviews)
"Location is excellent."
United States
Amund N.
The price is CA $350
CA $833 total
includes taxes & fees
Sep 24 - Sep 25
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

7. 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 $378
CA $1,112 total
includes taxes & fees
Sep 20 - Sep 21
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean, Golf and Sunset Views

8. 180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is CA $258
CA $941 total
includes taxes & fees
Sep 26 - Sep 27
180 Degree Ocean View in Wailea! WE204

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, (163 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
The price is CA $207
CA $744 total
includes taxes & fees
Sep 22 - Sep 23
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

10. Romantic, Luxury, Sensual Retreat - Couples Only

Romantic, Luxury, Sensual Retreat - Couples Only
Wailea
10.0 out of 10, Exceptional, (208 reviews)
"Just perfect! Amazing property and amazing location!"
United States
Jessica N.
The price is CA $447
CA $963 total
includes taxes & fees
Sep 20 - Sep 21
Romantic, Luxury, Sensual Retreat - Couples Only

11. Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi

Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
Wailea
9.8 out of 10, Exceptional, (201 reviews)
"Nice place, great location and can walk to many restaurants and resorts. Well stocked with essentials for cooking (wine glasses, plates, cutlery, etc.). Upstairs living room can get warm at sunset so a better AC would be helpful. "
United States
Craig P.
The price is CA $453
CA $1,492 total
includes taxes & fees
Sep 21 - Sep 22
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi

12. Polo Beach Club POL-109 by KBM

Polo Beach Club POL-109 by KBM
3.5 star property
Wailea
8.0 out of 10, Very good, (1 review)
"The property location was exactly what we wanted, easy access to the Wailea beachfront walking path and directly on the beach. We had a great time but if you are considering this place you need to go in with your eyes wide open. It was very pricey for how tired this unit is. It badly needs a full renovation. The tile is from the 1980's, the carpet is gross and crunchy. When we arrived late, it appeared someone had tried to break in the sliding doors and that set off numerous R&M emails...
Canada
PAMELA
The price is CA $1,675
CA $2,859 total
includes taxes & fees
Sep 26 - Sep 27
Polo Beach Club POL-109 by KBM

13. Totally renovated, closest to the beach!

Totally renovated, closest to the beach!
Wailea
9.8 out of 10, Exceptional, (231 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 $313
CA $905 total
includes taxes & fees
Sep 20 - Sep 21
Totally renovated, closest to the beach!

14. 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 $287
CA $780 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

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

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
Wailea
9.8 out of 10, Exceptional, (128 reviews)
"Wonderful, modern, great location condo!"
United States
Jaclyn G.
The price is CA $315
CA $907 total
includes taxes & fees
Sep 21 - Sep 22
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

16. Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!

Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!
South Kihei
9.6 out of 10, Exceptional, (19 reviews)
"Very nice condo with beach chairs, bogey board and clean quality furniture. would absolutely stay here again."
United States
Janie C.
The price is CA $900
CA $1,624 total
includes taxes & fees
Sep 27 - Sep 28
Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!

17. Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss

Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss
South Kihei
10.0 out of 10, Exceptional, (141 reviews)
"The view alone was worth the price of admission. The condo, was incidentally, well kept; well stocked; and very comfortable. In a nutshell; if you come to Maui; I would recommend this place. "
United States
Sono J.
The price is CA $787
CA $1,555 total
includes taxes & fees
Sep 26 - Sep 27
Maui / Kihei / Wailea Oceanfront 5-Star Condo: Newly Remodeled Beachfront Bliss

18. Wailea Ekahi Village | Remodeled Luxury 1-Bedroom Villa | Car Incl. w/ 6+ Nights | WKV-45C by KBM

Wailea Ekahi Village | Remodeled Luxury 1-Bedroom Villa | Car Incl. w/ 6+ Nights | WKV-45C by KBM
Wailea
10.0 out of 10, Exceptional, (6 reviews)
"Loved staying here! Beautiful recent renovation with high end touches. A little farther from the beach but still great Wailea location."
United States
Ayla W.
The price is CA $625
CA $1,608 total
includes taxes & fees
Sep 21 - Sep 22
Wailea Ekahi Village | Remodeled Luxury 1-Bedroom Villa | Car Incl. w/ 6+ Nights | WKV-45C by KBM

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 $131
CA $861 total
includes taxes & fees
Sep 20 - Sep 21
The Residences at Kamaole Sands Resort

20. Gorgeous Condo Two King Suites & Huge Ocean Views!

Gorgeous Condo Two King Suites & Huge Ocean Views!
Wailea
9.6 out of 10, Exceptional, (37 reviews)
"Great location. Clean, great lanai, family room was conformable. Enjoyed our time here and would stay again."
United States
Monica H.
The price is CA $471
CA $1,423 total
includes taxes & fees
Sep 22 - Sep 23
Gorgeous Condo Two King Suites & Huge Ocean Views!
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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