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

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (946 reviews)
"Great stay. Grounds were nice and clean. Staff was friendly. I would stay there again."
United States
Douglas Paul Zwerner or Laura
The price is CA $417
CA $495 total
includes taxes & fees
Jul 29 - Jul 30
Aston Maui Hill

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (2 reviews)
"Upscale and incredibly comfortable. This felt like a true upgrade from standard condos. The memory foam beds were heavenly, and the AC kept the place perfectly cool. We really appreciated the fast WiFi and having Netflix on the TV for relaxing evenings. Great gym onsite, too. We’ll definitely be back!"
United States
Sophie
The price is CA $207
CA $1,025 total
includes taxes & fees
Jul 22 - Jul 23
The Residences at Kamaole Sands Resort

Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (110 reviews)
"Excellent room"
United States
Rene
The price is CA $159
CA $494 total
includes taxes & fees
Jul 28 - Jul 29
Beautiful, Renovated, Hale Kamaole 159

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (34 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
The price is CA $64
CA $719 total
includes taxes & fees
Jul 23 - Jul 24
Signature Residences at Maui Banyan

LOWEST Rates in Wailea right now! Spacious 5-STAR Wailea Retreat🏝Corner unit

LOWEST Rates in Wailea right now! Spacious 5-STAR Wailea Retreat🏝Corner unit
Wailea
10.0 out of 10, Exceptional, (162 reviews)
"Very nice condo in a great location within walking distance to great shops, restaurants and the beach.Unfortunately we were only able to stay 6 out of our 15 nights we had booked due to a family emergency but we would definitely stay here again!Melissa was great to deal with!"
Canada
Theresa H.
The price is CA $313
CA $888 total
includes taxes & fees
Jul 31 - Aug 1
LOWEST Rates in Wailea right now! Spacious 5-STAR Wailea Retreat🏝Corner unit

Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (60 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 $221
CA $530 total
includes taxes & fees
Jul 26 - Jul 27
Romantic 1 BR Condo with King Tempurpedic

Kihei Surfside #108 - Ground Floor, Oceanfront, Sleeps 4

Kihei Surfside #108 - Ground Floor, Oceanfront, Sleeps 4
South Kihei
9.8 out of 10, Exceptional, (210 reviews)
"Amazing location and wonderful place. Our family LOVED it!"
United States
Kendra G.
Kihei Surfside #108 - Ground Floor, Oceanfront, Sleeps 4

Wailea Elua- CoralTree Residence Collection

Wailea Elua- CoralTree Residence Collection
3.5 star property
Wailea
9.6 out of 10, Exceptional, (257 reviews)
"Amazing trip"
United States
tammie
The price is CA $803
CA $1,510 total
includes taxes & fees
Aug 1 - Aug 2
Wailea Elua- CoralTree Residence Collection

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, (172 reviews)
"Great place to stay, close to beaches, and shops."
United States
Anonymous traveller
The price is CA $204
CA $546 total
includes taxes & fees
Aug 16 - Aug 17
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
10.0 out of 10, Exceptional, (4 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is CA $329
CA $1,037 total
includes taxes & fees
Jul 29 - Jul 30
180 Degree Ocean View in Wailea! WE204

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, (60 reviews)
"The beach was just across the street. Food and shopping near by was great. The complex was quiet and clean room. Had a great time, next in Maui will have to stay again. It was perfect! "
United States
Stephanie G.
The price is CA $189
CA $563 total
includes taxes & fees
Jul 21 - Jul 22
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

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, (227 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 $185
CA $576 total
includes taxes & fees
Jul 21 - Jul 22
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

130K Hawaiian Reno on Wailea Blue Golf *Ocean View
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 $307
CA $771 total
includes taxes & fees
Aug 1 - Aug 2
130K Hawaiian Reno on Wailea Blue Golf *Ocean View

Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet

Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet
Wailea
8.6 out of 10, Excellent, (42 reviews)
"Clean room and everything you need for a beach stay. "
United States
Glenn
The price is CA $297
CA $786 total
includes taxes & fees
Jul 21 - Jul 22
Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet

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 $165
CA $541 total
includes taxes & fees
Jul 21 - Jul 22
Perch - King Suite at Maui Banyan | Steps from the Beach | South Kihei Gem

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 $201
CA $540 total
includes taxes & fees
Jul 29 - Jul 30
Across from Kamaole 2 Beach, concrete building, well maintained.

Wailea Luxury Retreat | Walk to Beach & Shops

Wailea Luxury Retreat | Walk to Beach & Shops
Wailea
9.4 out of 10, Exceptional, (8 reviews)
"Excellent communication and the facilities were really nice with Two pools to choose from! Close to shops and walking paths "
United States
Jennifer A.
The price is CA $333
CA $989 total
includes taxes & fees
Jul 25 - Jul 26
Wailea Luxury Retreat | Walk to Beach & Shops

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, (90 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 $133
CA $600 total
includes taxes & fees
Jul 31 - Aug 1
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

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, (21 reviews)
"Just a wonderful stay. Everything is just right and the property is beautiful. "
United States
Roger B.
The price is CA $331
CA $808 total
includes taxes & fees
Jul 24 - Jul 25
Romantic, Luxury Maui Getaway with Ocean View - Couples Only

Beachside Retreat | Walk to Shops & Dining

Beachside Retreat | Walk to Shops & Dining
South Kihei
9.6 out of 10, Exceptional, (9 reviews)
"Nice place "
United States
Anonymous traveller
The price is CA $101
CA $710 total
includes taxes & fees
Jul 23 - Jul 24
Beachside Retreat | Walk to Shops & Dining
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 $495 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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