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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, (3689)
"Great area and great place to stay"
$185 nightly
The price is $218
Sep 2 - Sep 3
Total with taxes and fees
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2448)
"Great place! Room was a good size, very clean spacious, full kitchen, nice staff. We enjoyed our stay! "
$214 nightly
The price is $252
Sep 3 - Sep 4
Total with taxes and fees
Aston Maui Kaanapali Villas

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

10.0 out of 10, Exceptional, (263)
"Great location for whale watching, comfortable condo with well equipped kitchen, easy check in and check out"
$650 nightly
The price is $756
Sep 1 - Sep 2
Total with taxes and fees
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (223)
"Location was excellent "
$555 nightly
The price is $654
Sep 2 - Sep 3
Total with taxes and fees
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1653)
"Check-in was easy, the staff were very friendly and helpful. The room was clean and comfortable. Great place to stay."
$299 nightly
The price is $353
Sep 1 - Sep 2
Total with taxes and fees
Napili Shores Maui by OUTRIGGER

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (817)
"Condo was clean. Easy to check in and out. They have a shared grill that we used. All types of birds including chickens on property. "
Aston Maui Hill

Maui Beach Vacation Club

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

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2826)
"Beautiful resort! "
$833 nightly
The price is $896
Sep 6 - Sep 7
Total with taxes and fees
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

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very Good, (1381)
"A208 was terrific. We loved the view and the sound of ocean and accessibility to the beach. Would love to see a few more hooks in place to hang towels and some written information about sites and where to go etc. - like a welcome notebook "
Aston at Papakea Resort

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (431)
"Was an absolute beautiful place! "
AEI at Kaanapali Shores

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (912)
"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

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. "
$447 nightly
The price is $527
Sep 5 - Sep 6
Total with taxes and fees
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"
$694 nightly
The price is $818
Sep 28 - Sep 29
Total with taxes and fees
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"
$479 nightly
The price is $565
Sep 12 - Sep 13
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very Good, (2254)
"Great location for beach with beautiful garden views and easy close parking."
Castle Kama'ole Sands

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (466)
"Located on the beach with beautiful sunsets and large pool and hot tub."
Maui Sunset

Kaanapali Alii

4.0 star property
9.6 out of 10, Exceptional, (934)
"Great place"
Kaanapali Alii
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, 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 $218 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?

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.