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Wailea-Makena Holiday Rentals

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Our top choices for Wailea-Makena holiday 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 AU$717
includes taxes & fees
1 July - 2 July
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 AU$1,367
includes taxes & fees
9 July - 10 July
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 AU$963
includes taxes & fees
29 June - 30 June
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 AU$668
includes taxes & fees
5 July - 6 July
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 AU$506
includes taxes & fees
3 July - 4 July
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 AU$978
includes taxes & fees
5 July - 6 July
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 AU$856
includes taxes & fees
30 June - 1 July
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 AU$599
includes taxes & fees
9 July - 10 July
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 AU$818
includes taxes & fees
2 July - 3 July
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.
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.
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 AU$537
includes taxes & fees
27 June - 28 June
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 AU$553
includes taxes & fees
27 June - 28 June
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 AU$559
includes taxes & fees
27 June - 28 June
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 AU$931
includes taxes & fees
30 June - 1 July
Ekahi 27A: Priceless Ocean View from a Private Lanai

KKN-Get spoiled DLX Gr. Floor unit Mar.26-Apr.28-(Inquire) deal for all the days

KKN-Get spoiled DLX Gr. Floor unit Mar.26-Apr.28-(Inquire) deal for all the days
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 AU$578
includes taxes & fees
27 June - 28 June
KKN-Get spoiled DLX Gr. Floor unit Mar.26-Apr.28-(Inquire) deal for all the days

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 AU$540
includes taxes & fees
29 June - 30 June
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 AU$1,483
includes taxes & fees
4 July - 5 July
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 AU$1,086
includes taxes & fees
8 July - 9 July
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, (224 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 AU$618
includes taxes & fees
2 July - 3 July
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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Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wailea-Makena holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wailea-Makena holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wailea-Makena holiday rentals we have selected for you start as low as AU$668 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wailea-Makena rentals

At Expedia, we put the best Wailea-Makena holiday 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 holiday.

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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