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

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (28 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 $54
CA $705 total
includes taxes & fees
Jul 1 - Jul 2
Signature Residences at Maui Banyan

Ekahi Ocean View Escape and close to beach (21F)

Ekahi Ocean View Escape and close to beach (21F)
Wailea
9.8 out of 10, Exceptional, (71 reviews)
"Amazing location. Right near the beach. And a great complex!"
United States
Timothy J.
The price is CA $379
CA $1,366 total
includes taxes & fees
Jul 2 - Jul 3
Ekahi Ocean View Escape and close to beach (21F)

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 $142
CA $892 total
includes taxes & fees
Jun 29 - Jun 30
The Residences at Kamaole Sands Resort

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (931 reviews)
"Unit was spacious with great ocean view."
United States
DARSHAN
The price is CA $552
CA $655 total
includes taxes & fees
Jul 8 - Jul 9
Aston Maui Hill

Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (107 reviews)
"Excellent room"
United States
Rene
The price is CA $163
CA $503 total
includes taxes & fees
Jul 3 - Jul 4
Beautiful, Renovated, Hale Kamaole 159

180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
The price is CA $278
CA $978 total
includes taxes & fees
Jul 5 - Jul 6
180 Degree Ocean View in Wailea! WE204

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 $256
CA $817 total
includes taxes & fees
Jun 29 - Jun 30
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)
"Quite nice place, had everything we needed for our trip: air conditioning, laundry, well equipped kitchen to cook in"
United States
John P.
The price is CA $268
CA $596 total
includes taxes & fees
Jul 3 - Jul 4
Romantic 1 BR Condo with King Tempurpedic

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 $300
CA $795 total
includes taxes & fees
Jul 2 - Jul 3
Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet

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, (37 reviews)
"Amanda was great in responding to any of questions we had… The place was very nice and we really enjoyed our stay."
United States
Jennifer D.
The price is CA $277
CA $734 total
includes taxes & fees
Jul 15 - Jul 16
130K Hawaiian Reno on Wailea Blue Golf *Ocean View

Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi

Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi
Wailea
10.0 out of 10, Exceptional, (81 reviews)
"The location of this property is great! We enjoyed our stay."
United States
Shelby H.
The price is CA $507
CA $1,009 total
includes taxes & fees
Jul 2 - Jul 3
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi

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 host, location, and property. We really enjoyed our stay. The property was very quiet and relaxing. Hope to stay here again on future trips."
United States
Andrew W.
The price is CA $190
CA $525 total
includes taxes & fees
Jun 28 - Jun 29
Across from Kamaole 2 Beach, concrete building, well maintained.

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, (170 reviews)
"Great place to stay, close to beaches, and shops."
United States
Anonymous traveller
The price is CA $203
CA $542 total
includes taxes & fees
Jun 28 - Jun 29
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

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 $179
CA $547 total
includes taxes & fees
Jun 28 - Jun 29
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

Ekahi 27A: Priceless Ocean View from a Private Lanai

Ekahi 27A: Priceless Ocean View from a Private Lanai
Wailea
9.8 out of 10, Exceptional, (49 reviews)
"Ocean view! We loved it! We even slept great…Winning!!"
United States
Isabel P.
The price is CA $312
CA $891 total
includes taxes & fees
Jul 24 - Jul 25
Ekahi 27A: Priceless Ocean View from a Private Lanai

KKN-Get spoiled DLX Gr. floor till July 9 with in unit washer, bath & golf clubs

KKN-Get spoiled DLX Gr. floor till July 9 with in unit washer, bath & golf clubs
South Kihei
9.6 out of 10, Exceptional, (121 reviews)
"The condo was perfect for our family of 4. We enjoyed the pool. It’s a great location in Kīhei. The owners are friendly and quick to respond. "
United States
Brenna K.
The price is CA $248
CA $664 total
includes taxes & fees
Jul 2 - Jul 3
KKN-Get spoiled DLX Gr. floor till July 9 with in unit washer, bath & golf clubs

TOP FLOOR CORNER PRIVATE STUDIO, LOCALLY OWNED, CLEAN, WALK TO BEACH

TOP FLOOR CORNER PRIVATE STUDIO, LOCALLY OWNED, CLEAN, WALK TO BEACH
Wailea
9.8 out of 10, Exceptional, (99 reviews)
"This place was perfect!"
United States
Ben H.
The price is CA $247
CA $578 total
includes taxes & fees
Jun 29 - Jun 30
TOP FLOOR CORNER PRIVATE STUDIO, LOCALLY OWNED, CLEAN, WALK TO BEACH

Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled

Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled
South Kihei
9.6 out of 10, Exceptional, (67 reviews)
"Everything was as advertised and the place was great! "
United States
Pratik P.
The price is CA $446
CA $1,480 total
includes taxes & fees
Jul 4 - Jul 5
Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled

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 $299
CA $955 total
includes taxes & fees
Jun 28 - Jun 29
Wailea Luxury Retreat | Walk to Beach & Shops

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, (225 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 $209
CA $611 total
includes taxes & fees
Jul 2 - Jul 3
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
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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