Wailea-Makena Holiday Rentals

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Our top choices for Wailea-Makena holiday rentals

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (907 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
The price is AU$405
includes taxes & fees
8 June - 9 June
Aston Maui Hill

Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (4 reviews)
"Clean everything great time great location! "
United States
Sean
The price is AU$3,331
includes taxes & fees
12 May - 13 May
Grand Champions by KBM

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
9.0 out of 10, Wonderful, (22 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$732
includes taxes & fees
5 June - 6 June
Signature Residences at Maui Banyan

Stunning Property in Building 10 of Kamaole Sands

Stunning Property in Building 10 of Kamaole Sands
South Kihei
10.0 out of 10, Exceptional, (68 reviews)
"The condo was well equipped, clean, great location and the owner was super responsive. Would highly recommend staying here."
United States
Carol M.
The price is AU$1,266
includes taxes & fees
24 May - 25 May
Stunning Property in Building 10 of Kamaole Sands

Kamaole Sands Condos Close to Beach with Parking

Kamaole Sands Condos Close to Beach with Parking
3.5 star property
South Kihei
9.6 out of 10, Exceptional, (4 reviews)
"Clean property nice room good location"
United States
Richard
The price is AU$688
includes taxes & fees
12 May - 13 May
Kamaole Sands Condos Close to Beach with Parking

Steps to Kamaole 3 Beach

Steps to Kamaole 3 Beach
South Kihei
9.2 out of 10, Wonderful, (30 reviews)
"Excellent 2 bedroom with friendly Owner - Josh - was very nice and helpful when we had questions prior to the trip. We thought about buying a condo as we liked the area very much!"
Canada
Mark M.
Steps to Kamaole 3 Beach

Mana Kai 608: Oceanfront Remodel! Modern Surf Vibe 🌊

Mana Kai 608: Oceanfront Remodel! Modern Surf Vibe 🌊
South Kihei
10.0 out of 10, Exceptional, (75 reviews)
"Fantastic Beach! Wonderful Views! Very clean and organized."
United States
Anonymous traveller
The price is AU$1,412
includes taxes & fees
13 May - 14 May
Mana Kai 608: Oceanfront Remodel! Modern Surf Vibe 🌊

Beautiful Oceanfront Ohana: Fabulous Views, Pool, A/C, Best Beach & WOW Sunsets

Beautiful Oceanfront Ohana: Fabulous Views, Pool, A/C, Best Beach & WOW Sunsets
South Kihei
10.0 out of 10, Exceptional, (23 reviews)
"Lovely property! Easy access to the best beach!"
United States
Matt S.
Beautiful Oceanfront Ohana: Fabulous Views, Pool, A/C, Best Beach & WOW Sunsets

Fantastic Ocean View Steps to Kamaole Beach 3

Fantastic Ocean View Steps to Kamaole Beach 3
South Kihei
9.8 out of 10, Exceptional, (33 reviews)
"The unit was clean and offered great amenities. The location was perfect as it is close to the beach. The host was great to communicate with. Would stay here again! "
United States
Sarah H.
The price is AU$711
includes taxes & fees
13 May - 14 May
Fantastic Ocean View Steps to Kamaole Beach 3

Newly Remodeled Directly Across the Street from Kamaole 3 Beach

Newly Remodeled Directly Across the Street from Kamaole 3 Beach
South Kihei
10.0 out of 10, Exceptional, (26 reviews)
"Clean, comfortable, great location! "
United States
Kiana O.
The price is AU$946
includes taxes & fees
21 May - 22 May
Newly Remodeled Directly Across the Street from Kamaole 3 Beach

Ocean View Large Lanai Kamaole Sands

Ocean View Large Lanai Kamaole Sands
South Kihei
10.0 out of 10, Exceptional, (2 reviews)
"The condo was well kept and had everything we needed! The location was phenomenal. The host was very responsive!"
United States
Valerie S.
The price is AU$697
includes taxes & fees
14 May - 15 May
Ocean View Large Lanai Kamaole Sands

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 AU$7,096
includes taxes & fees
22 May - 23 May
Polo Beach Club POL-109 by KBM

Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!

Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!
South Kihei
9.6 out of 10, Exceptional, (19 reviews)
"We loved it here, beautiful sunset views, very clean and stocked with everything we needed. Thank you. "
United States
Marcy S.
The price is AU$1,591
includes taxes & fees
12 May - 13 May
Oceanview On Beach Dream Suite- King/1-Bath, Balcony, Kitchen & Living Area!

Split Layout 2 master bedrooms, walk to beach

Split Layout 2 master bedrooms, walk to beach
South Kihei
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay here! Apartment is clean and comfortable and close to everything that you need. It is organized and equipped very well."
United States
Jon M.
The price is AU$1,032
includes taxes & fees
13 May - 14 May
Split Layout 2 master bedrooms, walk to beach

🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈

🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea
10.0 out of 10, Exceptional, (162 reviews)
"The unit is big and comfortable, very clean, the access code setup works well (no keys), and the host was very accommodating ."
United States
pia
The price is AU$821
includes taxes & fees
12 May - 13 May
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈

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, (68 reviews)
"This condo has everything you need for an amazing stay in Maui! This was our first time here and it has exceeded all our expectations. Thank you to our hosts for sharing this wonderful space with us, we’re already planning our next trip back!"
United States
Mary C.
The price is AU$1,301
includes taxes & fees
14 May - 15 May
Ekahi Ocean View Escape and close to beach (21F)

Steps to Kamaole 3 Beach!

Steps to Kamaole 3 Beach!
South Kihei
9.6 out of 10, Exceptional, (15 reviews)
"Condo was very nice but not quite as comfortable as others f. Feels a bit like a show home or a hotel . But all in all , we love Hale Kamaole and enjoy being here always . "
Canada
Michael W.
Steps to Kamaole 3 Beach!

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$982
includes taxes & fees
13 May - 14 May
Wailea Luxury Retreat | Walk to Beach & Shops

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$745
includes taxes & fees
24 May - 25 May
Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet

Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews

Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews
South Kihei
9.6 out of 10, Exceptional, (67 reviews)
"Second trip to Kihei. Absolutely loved this condo. Location is perfect. super clean. Lisa was accommodating and responsive. She was a joy to work with. The small things are what really added to the experience. Meaning there were basic condiments available cleaning supplies some paper products so after a long trip, shopping was less urgent. And when you’re on vacation, anything that makes things less urgent adds to the experience. If I were to own a short term rental, this is how I’d like it...
United States
Otavio B.
The price is AU$1,104
includes taxes & fees
14 May - 15 May
Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews
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

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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$405 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.