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 $393
CA $466 total
includes taxes & fees
Oct 18 - Oct 19
Aston Maui Hill

2. Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection
4.0 star property
Wailea
9.4 out of 10, Exceptional, (117 reviews)
"Most beautiful view"
United States
Vesselina
Makena Surf - CoralTree Residence Collection

3. 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 $481
CA $1,257 total
includes taxes & fees
Sep 21 - Sep 22
Grand Champions by KBM

4. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (38 reviews)
"The room was rather small. Limited furniture other than beds. Bathroom was also small and very dated. Beds were verycomfortable though."
United States
Stacie
The price is CA $55
CA $698 total
includes taxes & fees
Sep 21 - Sep 22
Signature Residences at Maui Banyan

5. 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. 🏝

6. Sunny Top Floor Studio 10 Minute Walk from Wailea Beaches

Sunny Top Floor Studio 10 Minute Walk from Wailea Beaches
Wailea
9.0 out of 10, Wonderful, (113 reviews)
"Would absolutely rent again! Great property!"
United States
taylor m.
Sunny Top Floor Studio 10 Minute Walk from Wailea Beaches

7. 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 $450
CA $1,489 total
includes taxes & fees
Sep 21 - Sep 22
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi

8. 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, (38 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 $209
CA $629 total
includes taxes & fees
Oct 17 - Oct 18
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

9. #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 $326
CA $855 total
includes taxes & fees
Sep 25 - Sep 26
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

10. 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.
Gorgeous Condo Two King Suites & Huge Ocean Views!

11. 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 $195
CA $849 total
includes taxes & fees
Sep 18 - Sep 19
180 Degree Ocean View in Wailea! WE204

12. 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 $525 total
includes taxes & fees
Sep 28 - Sep 29
Romantic 1 BR Condo with King Tempurpedic

13. 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

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 $117
CA $832 total
includes taxes & fees
Sep 20 - Sep 21
The Residences at Kamaole Sands Resort

15. 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 $555
CA $1,373 total
includes taxes & fees
Sep 25 - Sep 26
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

16. 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 $295
CA $789 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

17. Wailea Garden-View Condo – Lanai, A/C, New Furnishings & Near Golf

Wailea Garden-View Condo – Lanai, A/C, New Furnishings & Near Golf
Wailea
9.4 out of 10, Exceptional, (10 reviews)
"Everything was as stated and the property was great!"
United States
Nicholas N.
The price is CA $774
CA $976 total
includes taxes & fees
Sep 30 - Oct 1
Wailea Garden-View Condo – Lanai, A/C, New Furnishings & Near Golf

18. 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, (59 reviews)
"Location is excellent."
United States
Amund N.
The price is CA $348
CA $820 total
includes taxes & fees
Sep 25 - Sep 26
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

19. 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, (72 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.
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

20. 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 $445
CA $958 total
includes taxes & fees
Sep 27 - Sep 28
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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Everything you need to know about Wailea-Makena vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wailea-Makena vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wailea-Makena vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wailea-Makena. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wailea-Makena vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wailea-Makena vacation rentals we have selected for you start as low as CA $466 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

At Expedia, we put the best Wailea-Makena vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wailea-Makena rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wailea-Makena vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wailea-Makena. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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