Photo by Claire Houston

Olowalu Holiday Rentals

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Holiday Rentals in Olowalu

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3350)
"Great room, great view, great pool, family had a great time. "
The price is AU$727
includes taxes & fees
28 Nov - 29 Nov
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2627)
"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "
The price is AU$1,154
includes taxes & fees
14 Dec - 15 Dec
OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1080)
"Great property in perfect location adjacent to walking path & snorkeling beach. We loved our one-bedroom unit and enjoyed the resorts amenities including pools and restaurants. Well maintained, very clean, friendly staff, wish we could have extended our stay, but not easy to do at a timeshare property like you can at a hotel. That said, we wouldn't hesitate to return, next time for a longer visit. Mahalo!"
The price is AU$873
includes taxes & fees
5 Dec - 6 Dec
The Westin Ka'anapali Ocean Resort Villas

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2300)
"Leann at the front desk is amazing!!!"
The price is AU$703
includes taxes & fees
7 Dec - 8 Dec
Aston Maui Kaanapali Villas

Kaanapali Alii

4.0 star property
9.6 out of 10, Exceptional, (838)
"It needs a bar"
Kaanapali Alii

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1574)
"We love this place. We stay here to relax and enjoy the view. Also the staff is wonderful!"
Aston Mahana at Kaanapali

The Whaler Resort Kaanapali Beach

4.0 star property
9.4 out of 10, Exceptional, (118)
"Amazing! Right on the beach. Staff was friendly and incredible. Had the best experience! Can’t wait to be back. "
The Whaler Resort Kaanapali Beach

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1022)
"The beach was in your backyard. I’ve seen multiple turtles. There’s a cute delicious deli on the property. Away from the busy areas but close enough for a short drive. Just a perfect getaway "
Sugar Beach Resort

Napili Shores Maui by OUTRIGGER

3.0 star property
8.8 out of 10, Excellent, (1533)
"Can’t say enough good things about Napili Shores to stay will definitely be back"
Napili Shores Maui by OUTRIGGER

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (699)
"Great!"
Maui Beach Vacation Club

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (752)
"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...
Aston Maui Hill

Castle Napili Surf Beach Resort

3.5 star property
10.0 out of 10, Exceptional, (78)
"This property was in a prime location, best beach in Maui. "
Castle Napili Surf Beach Resort

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1447)
"We loved our time at the Whaler however our room needed an upgrade as it looked like it was from the 80’s. Everything else perfect. Staff wonderful!!"
The price is AU$1,146
includes taxes & fees
14 Dec - 15 Dec
Aston at The Whaler on Kaanapali Beach

Napili Sunset on the Beach

2.5 star property
9.2 out of 10, Wonderful, (600)
"Very Nice Soot! Cozy!"
The price is AU$391
includes taxes & fees
2 Dec - 3 Dec
Napili Sunset on the Beach

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1353)
"Originally we were checked into a smaller 3rd story room when we believed we were supposed to have a different ground floor. We advised them at check in, and though we would have still had a great vacation in this room, the management quickly remedied the situation and made our stay so much more pleasant. Everyone was so kind and gracious. The property and stay were perfect!"
Aston at Papakea Resort

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (403)
"The pool and the location of the proximity to the rims was very good also the proximity to Beach and the view of the ocean was very nice and the proximity to shopping and dining was very good also the only thing we did not really like is the size of the restrooms and the updating of the restrooms were not very good and they should be renovated "
Maui Sunset

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (494)
"It is a nice rental property in a nice location overall. It has multiple buildings and units with b ACH direct access. There are several swimming pools, many people have fun playing in swimming poor. Also it is one of best sunsets from the main swimming poor and from the central lawn field. I am really enjoyed. The unit we stayed is large one bed room equipped with a full kitchen set, if someone like cook inside. There are many high ended restaurants and a shopping mall in a short during...
Wailea Ekahi - CoralTree Residence Collection

Kapalua Villas Maui

4.0 star property
8.6 out of 10, Excellent, (910)
"Loved the property and location. Only issue is that eating establishments are somewhat limited in variety and price and most require advance reservations. I found I would drive to kanapali for more options"
The price is AU$1,204
includes taxes & fees
12 Dec - 13 Dec
Kapalua Villas Maui

Maui Kamaole

3.5 star property
8.8 out of 10, Excellent, (819)
"Beautiful time as usual…"
Maui Kamaole

The Gardens at West Maui

3.0 star property
8.4 out of 10, Very good, (436)
"Lisa at the front desk was so friendly, helpful and a delight, really enjoyed this property. Would recommend it too others."
The Gardens at West Maui
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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Other types of properties in Olowalu you may be interested in

Fairmont Kea Lani Maui

4.5 star property
9.4 out of 10, Exceptional, (1076)
"World class resort with the Aloha spirit."
The price is AU$1,204
includes taxes & fees
4 Dec - 5 Dec
Fairmont Kea Lani Maui

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3350)
"Great room, great view, great pool, family had a great time. "
The price is AU$727
includes taxes & fees
28 Nov - 29 Nov
Aston Kaanapali Shores

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1025)
"The staff is very friendly and dining options are amazing! The resort has so many complimentary activities to participate, would be visiting again."
The price is AU$1,448
includes taxes & fees
30 Nov - 1 Dec
Four Seasons Resort Maui at Wailea
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Olowalu?

Yes, there are holiday rentals close to the most popular sights in Olowalu, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Olowalu has to offer?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: This holiday home rental outside of Olowalu is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Olowalu?

West Maui Mountains and Mile Marker 14 Beach are a couple of lovely local spots to get outside and enjoy nature. Kaanapali Beach and Iao Valley State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Olowalu like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Olowalu. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.