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Olowalu Vacation Rentals

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Vacation Rentals in Olowalu

Our top choices for Olowalu vacation rentals

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3695)
"Great area and great place to stay"
The price is CA $209
CA $287 total
includes taxes & fees
Sep 2 - Sep 3
Aston Kaanapali Shores

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

10.0 out of 10, Exceptional, (263)
"We loved our stay! The views are breathtaking, we felt like we were on our own little private beach, and the condo had everything we needed for a wonderful vacation. We saw turtles everyday and loved sitting on the lanai/patio and looking at the ocean. "
The price is CA $433
CA $965 total
includes taxes & fees
Sep 2 - Sep 3
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2449)
"Great place! Room was a good size, very clean spacious, full kitchen, nice staff. We enjoyed our stay! "
The price is CA $179
CA $333 total
includes taxes & fees
Sep 2 - Sep 3
Aston Maui Kaanapali Villas

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (225)
"Perfect location right on the beach. Shopping and restaurants next door."
The price is CA $307
CA $885 total
includes taxes & fees
Sep 2 - Sep 3
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1654)
"Check-in was easy, the staff were very friendly and helpful. The room was clean and comfortable. Great place to stay."
The price is CA $384
CA $453 total
includes taxes & fees
Sep 15 - Sep 16
Napili Shores Maui by OUTRIGGER

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (819)
"The apartment was big, equipped with everything. The style is a bit "old" and it could use a freshen up but it is cozy. All the complex run mainly on solar power that is a plus."
Aston Maui Hill

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2829)
"Really liked the resort"
The price is CA $434
CA $1,143 total
includes taxes & fees
Oct 2 - Oct 3
OUTRIGGER Honua Kai Resort & Spa

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1483)
"It was a nice place to stay"
Aston at The Whaler on Kaanapali Beach

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (792)
"Just a great stay! "
Maui Beach Vacation Club

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very good, (915)
"Great Aloha spirit and a great location and pool."
Kahana Falls Maui by VRI Americas

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (11)
"We had an amazing vacation with our kids and grandkids. We have already booked again for next year"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1382)
"Everything was excellent "
Aston at Papakea Resort

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1113)
"The resort was beautiful. The hospitality in all seas was top notch. "
The price is CA $614
CA $725 total
includes taxes & fees
Sep 7 - Sep 8
The Westin Ka'anapali Ocean Resort Villas

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1643)
"Beautiful location "
Aston Mahana at Kaanapali

Kapalua Villas Maui

4.0 star property
8.8 out of 10, Excellent, (952)
"The view of the ocean was great and I was happy just to be there. It was old and a little poorly built, windows or doors were hard to open, etc. Some renovated parts were comfortable. The dryer was broken, which was inconvenient, but housekeeping provided new towels daily and offered to do laundry for free. Cooking utensils were very well stocked"
The price is CA $316
CA $1,102 total
includes taxes & fees
Oct 1 - Oct 2
Kapalua Villas Maui

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (466)
"Very nice place to stay"
The price is CA $658
CA $777 total
includes taxes & fees
Sep 16 - Sep 17
The Westin Nanea Ocean Villas, Ka'anapali

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (468)
"Good place to spend your vacation "
Maui Sunset

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very good, (2255)
"Great location for beach with beautiful garden views and easy close parking."
Castle Kama'ole Sands

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very good, (709)
"Great place to stay "
Kahana Beach Vacation Club

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (434)
"Great location and good beachfront!"
AEI at Kaanapali Shores
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

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Olowalu vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olowalu vacation rentals we have selected for you start as low as CA $179 per night. Entering your travel dates in the search wizard 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?

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach: This vacation home rental near Olowalu is located in the city center and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Olowalu?

Explore the area and family-friendly sights such as Maui Fish Pipe, 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.