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

Wailea-Makena Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Wailea-Makena vacation rentals

A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

1. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (37 reviews)
"Wonderful location, a short walk to restaurants, shops and beaches. The condo and property grounds were VERY well taken care of and groomed. Beautiful gardens and waterfalls. The pools were very relaxing and our experience was definitely one we will remember. A++"
United States
Patrick
The price is CA $67
CA $719 total
includes taxes & fees
Sep 15 - Sep 16
Signature Residences at Maui Banyan
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

2. 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 $158
CA $915 total
includes taxes & fees
Sep 17 - Sep 18
The Residences at Kamaole Sands Resort
A balcony with a view of a sunset over palm trees and a row of modern buildings.

3. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"I’ve stayed at several units in the same complex and this one was one of the best. Nicely appointed and a great view from the lanai. The bed was very comfy and the AC worked great. It’s so nice to be able to walk across the street to such a nice beach, we even saw a turtle in the water."
United States
Daniel L.
Beautiful, Renovated, Hale Kamaole 159
A residential area with a two-story building, a staircase, and various trees and shrubs.

4. 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 $208
CA $631 total
includes taxes & fees
Oct 9 - Oct 10
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

5. 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 $218
CA $525 total
includes taxes & fees
Sep 20 - Sep 21
Romantic 1 BR Condo with King Tempurpedic
A beach with palm trees and a clear sky.

6. 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 $248
CA $795 total
includes taxes & fees
Sep 14 - Sep 15
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A beach scene with two people standing near rocks.

7. Kameole Beach II across street - Feel Soft Sand on Your Toes and Find Your Aloha

Kameole Beach II across street - Feel Soft Sand on Your Toes and Find Your Aloha
South Kihei
9.6 out of 10, Exceptional, (122 reviews)
"Beach is closed, shops located around"
United States
Yelena M.
Kameole Beach II across street - Feel Soft Sand on Your Toes and Find Your Aloha
A pathway leading to a beach with dense green foliage on either side.

8. #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
9.8 out of 10, Exceptional, (97 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 $145
CA $778 total
includes taxes & fees
Sep 17 - Sep 18
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A spacious room with a large wooden dining table, comfortable seating, a bookshelf, and a view of the ocean through large sliding doors.

9. 180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
10.0 out of 10, Exceptional, (5 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is CA $272
CA $956 total
includes taxes & fees
Oct 1 - Oct 2
180 Degree Ocean View in Wailea! WE204

10. Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem

Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem
South Kihei
9.0 out of 10, Wonderful, (2 reviews)
"Checkin was very fast, and easy to navigate. Talked with a front desk person and that was it.The location is great, only a 5-10 minute walk down to the beach and very close to downtown Kihei!"
United States
Anthony N.
The price is CA $163
CA $535 total
includes taxes & fees
Sep 19 - Sep 20
Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem
A balcony with wicker furniture, a glass table, and a view of palm trees and a building across the street.

11. 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, (173 reviews)
"Perfect location, great parking. Excellent value and manager was wonderful. "
United States
Cheyenne M.
The price is CA $198
CA $534 total
includes taxes & fees
Sep 14 - Sep 15
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
A beach with people swimming and sunbathing, palm trees, and a building in the background.

12. Across from Kamaole 2 Beach, concrete building, well maintained.

Across from Kamaole 2 Beach, concrete building, well maintained.
South Kihei
10.0 out of 10, Exceptional, (165 reviews)
"Great location!"
United States
Tyler B.
The price is CA $186
CA $515 total
includes taxes & fees
Sep 23 - Sep 24
Across from Kamaole 2 Beach, concrete building, well maintained.
A sandy beach with footprints, a few people, and a boat.

13. 1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
South Kihei
9.4 out of 10, Exceptional, (61 reviews)
"great place for walking to the beach"
United States
Kim & Tom C.
The price is CA $175
CA $540 total
includes taxes & fees
Sep 14 - Sep 15
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
A resort with a swimming pool, palm trees, and ocean views.

14. 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 $425
CA $505 total
includes taxes & fees
Oct 12 - Oct 13
Aston Maui Hill
A spacious living room with a glass coffee table, a sofa, and a chair. There is a balcony with a view of palm trees and houses.

15. Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches

Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
Wailea
9.6 out of 10, Exceptional, (173 reviews)
"The communication with the host was superb, the amenities were generous and the location was fantastic."
United States
Howard G.
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
A beach scene with a blue cylindrical object in the foreground.

16. Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.

Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
South Kihei
10.0 out of 10, Exceptional, (228 reviews)
"The location right next to the water and the wonderful amenities were just what we needed! Might have to come here again!"
United States
Paulina B.
The price is CA $178
CA $563 total
includes taxes & fees
Sep 20 - Sep 21
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
A pool area with lounge chairs, palm trees, and a covered seating area.

17. Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C

Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
South Kihei
9.8 out of 10, Exceptional, (133 reviews)
"We had a great stay at the condo. The location was perfect. The condo was spotless and the amenities very useful, especially all the beach equipment. And thanks for the snacks and candy that were there when we arrived."
United States
Bob J.
The price is CA $207
CA $602 total
includes taxes & fees
Oct 1 - Oct 2
Ocean View Maui Condo Right Across from the Beach! 1 of 6 larger MK condos, A/C
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

18. 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 $130
CA $592 total
includes taxes & fees
Sep 18 - Sep 19
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A swimming pool with lounge chairs and a covered area, surrounded by palm trees and a clear sky.

19. One Bedroom Ocean View

One Bedroom Ocean View
South Kihei
10.0 out of 10, Exceptional, (4 reviews)
"Good"
United States
Hobum L.
The price is CA $153
CA $607 total
includes taxes & fees
Sep 15 - Sep 16
One Bedroom Ocean View
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

20. 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.
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wailea-Makena Hotel Reviews

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"Loved this resort"
Amalia 4-night trip
Posted 19 hours ago
Wailea Beach Resort - Marriott, Maui

Find out more about Wailea-Makena

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 $505 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. 

Explore a world of travel with Expedia