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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (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 CA $338
CA $401 total
includes taxes & fees
Jun 8 - Jun 9
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 CA $1,966
CA $3,231 total
includes taxes & fees
May 13 - May 14
Grand Champions by KBM

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (24 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 $53
CA $681 total
includes taxes & fees
May 14 - May 15
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 CA $511
CA $1,277 total
includes taxes & fees
May 13 - May 14
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 CA $230
CA $699 total
includes taxes & fees
May 15 - May 16
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.
The price is CA $645
CA $799 total
includes taxes & fees
May 27 - May 28
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 CA $718
CA $1,425 total
includes taxes & fees
May 13 - May 14
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.
The price is CA $437
CA $1,114 total
includes taxes & fees
May 14 - May 15
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 CA $576
CA $705 total
includes taxes & fees
May 13 - May 14
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 CA $763
CA $943 total
includes taxes & fees
May 21 - May 22
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 CA $602
CA $743 total
includes taxes & fees
May 24 - May 25
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 CA $5,321
CA $7,033 total
includes taxes & fees
May 23 - May 24
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 CA $880
CA $1,588 total
includes taxes & fees
May 26 - May 27
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 CA $500
CA $1,034 total
includes taxes & fees
May 13 - May 14
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 CA $269
CA $815 total
includes taxes & fees
May 13 - May 14
🐬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, (69 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 CA $365
CA $1,316 total
includes taxes & fees
May 30 - May 31
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.
The price is CA $458
CA $571 total
includes taxes & fees
Jun 11 - Jun 12
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 CA $343
CA $986 total
includes taxes & fees
May 17 - May 18
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 CA $280
CA $755 total
includes taxes & fees
May 24 - May 25
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 CA $412
CA $1,090 total
includes taxes & fees
May 18 - May 19
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.
Save an average of 15% on thousands of hotels when you're signed in

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.