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Olowalu Vacation Rentals

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Our top choices for Olowalu vacation rentals

Condo resort in South Kihei

Signature Residences at Maui Banyan
4.5 star property
9.6 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
$493 nightly
The price is $585
Jan 1 - Jan 2, 2026
Total with taxes and fees
Signature Residences at Maui Banyan
9.4 out of 10, Exceptional, (196)
"Very quiet safe place. "
Canada
Monica
$377 nightly
The price is $442
Jan 7 - Jan 8, 2026
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
9.2 out of 10, Wonderful, (19)
"Clean and convenient"
United States
Ilya L
$375 nightly
The price is $377
Jan 22 - Jan 23, 2026
Total with taxes and fees
Kuau Surf 2.0 Maui North Shore Locally-Owned

Condo resort in Lahaina

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2889)
"Wonderful stay! "
United States
Quiauna
$932 nightly
The price is $1,016
Jan 15 - Jan 16, 2026
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
9.6 out of 10, Exceptional, (331)
"Amazing resort second time being here will definitely be back next year "
United States
David
$608 nightly
The price is $722
Jan 16 - Jan 17, 2026
Total with taxes and fees
The Whaler Resort Kaanapali Beach

Apartment in South Kihei

The Ocean View Residence
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
$503 nightly
The price is $613
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Ocean View Residence
10.0 out of 10, Exceptional, (267)
"Great stay"
United States
Noah C.
$335 nightly
The price is $392
Jan 9 - Jan 10, 2026
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Aparthotel in Lahaina

Aston Kaanapali Shores
3.5 star property
8.8 out of 10, Excellent, (3931)
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
United States
Candida
$339 nightly
The price is $403
Jan 17 - Jan 18, 2026
Total with taxes and fees
Aston Kaanapali Shores

Aparthotel in South Kihei

Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (858)
"Clean room, attentive staff, and tons of things for kids and adults alike to do! "
United States
Misty
$454 nightly
The price is $539
Jan 9 - Jan 10, 2026
Total with taxes and fees
Aston Maui Hill
9.4 out of 10, Exceptional, (84)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo, great views and location"
United States
Pam B.
$547 nightly
The price is $638
Jan 28 - Jan 29, 2026
Total with taxes and fees
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
9.6 out of 10, Exceptional, (161)
"Everything was great. Kitchen well stocked, beautiful view. "
United States
Eric S.
$467 nightly
The price is $547
Jan 23 - Jan 24, 2026
Total with taxes and fees
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
9.8 out of 10, Exceptional, (74)
"This was our first stay in Kihei and we had a wonderful time! The location was great and we appreciated the quietness of our space. We were able to walk to a nearby shopping plaza where we found delicious food and coffee. Our host was kind and communicated promptly and efficiently. We will be back! "
United States
Paige O.
$483 nightly
The price is $566
Jan 6 - Jan 7, 2026
Total with taxes and fees
Oceanfront penthouse with amazing views at Kauhale Makai
9.4 out of 10, Exceptional, (131)
"The view is amazing"
United States
Carlos A.
$578 nightly
The price is $674
Jan 19 - Jan 20, 2026
Total with taxes and fees
Oceanfront condo with pool & balcony - walk to dining, activities, and more
8.8 out of 10, Excellent, (8)
"We had a great time. Made room for 8 of us. Could use a little maintenance on a couple things to make them easier to use. We would definitely book there again"
United States
Kevin D.
$591 nightly
The price is $692
Jan 13 - Jan 14, 2026
Total with taxes and fees
Paia 2 Bedroom 2 Bathroom
10.0 out of 10, Exceptional, (31)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
$445 nightly
The price is $521
Jan 3 - Jan 4, 2026
Total with taxes and fees
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
9.4 out of 10, Exceptional, (57)
"Check in was very easy and this is a perfect location for ocean access. "
Canada
Tracy C.
$313 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Condo in Maalaea Bay

Romantic Beachfront Getaway
9.6 out of 10, Exceptional, (39)
"We were rarely there except to sleep but the apartment has everything we needed. It’s walking distance to the harbor and ocean center. The beach is literally steps outside. The owner was very quickly responsive to our questions."
United States
Amy S.
$391 nightly
The price is $497
Jan 1 - Jan 2, 2026
Total with taxes and fees
Romantic Beachfront Getaway
9.6 out of 10, Exceptional, (165)
"Desperately needs AC in the bedroom!"
United States
Tami M.
$431 nightly
The price is $505
Jan 20 - Jan 21, 2026
Total with taxes and fees
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking

Aparthotel in Lahaina

Aston Maui Kaanapali Villas
3.0 star property
8.8 out of 10, Excellent, (2527)
"Very helpful and friendly staff. Easy walk to other hotels and restaurants. Beautiful beach. "
United States
Sally
$390 nightly
The price is $462
Jan 1 - Jan 2, 2026
Total with taxes and fees
Aston Maui Kaanapali Villas
9.6 out of 10, Exceptional, (18)
"Great place to stay! Our family of a 1 year old and 6 adults stayed at this Condo in Kihei for 5 days. The condo was clean and supplied with everything we needed- from beach gear to baby accommodations (high chair and pack n play). The beach is within walking distance. The parking stalls were compact size and a little tight for the suv we had but other than that everything met our expectations. Communication with Rebecca (the owner) was great, she responded as soon as she could. Overall it was...
United States
Nicole G.
$443 nightly
The price is $520
Jan 24 - Jan 25, 2026
Total with taxes and fees
100% Walk Score to Eat & Play Across from Kamaolé Beach. 2bd 2bd AC Kihei Condo
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 Olowalu Hotel Reviews

Find out more about Olowalu

Everything you need to know about Olowalu 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 Olowalu vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Olowalu vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Olowalu vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Olowalu. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Olowalu in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $403 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Olowalu rentals

At Expedia, we put the best Olowalu 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 Olowalu 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 Olowalu 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 Olowalu. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Olowalu?

Yes, we have vacation rentals near the most popular local attractions in Olowalu, or you can go with a secluded option if you want a relaxing place to stay. Olowalu is known for its shopping and restaurants. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation rentals that Olowalu has to offer?

Kaiholo Hale: This vacation home rental near Olowalu is by the ocean and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

What’s there to see and do in Olowalu?

Explore the area and family-friendly sights such as Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters, or get out into nature at a spot like Mile Marker 14 Beach. Kaanapali Beach and Wailea Beach are other popular places to visit in the area.

What’s a vacation rental in Olowalu like?

A vacation rental is a private property you can stay in for several days or longer in Olowalu. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.