Photo by Claire Houston

Olowalu Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Holiday Rentals in Olowalu

Our top choices for Olowalu holiday rentals

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3743)
"Great stay. Do not hesitate to book this hotel, we had a great time and great view. "
The price is S$449
includes taxes & fees
27 Sept - 28 Sept
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2457)
"Great family resort! Huge room that was perfect for our family of 5. 2 bedrooms and a huge kitchen/living room made for the perfect staycation on Island. "
The price is S$458
includes taxes & fees
27 Sept - 28 Sept
Aston Maui Kaanapali Villas
The Whaler Resort Kaanapali Beach
Exterior

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (241)
"We had a lovely stay! I would recommend this place especially for honeymooners. "
The price is S$901
includes taxes & fees
20 Oct - 21 Oct
The Whaler Resort Kaanapali Beach
Kahana Falls Maui by VRI Americas
Living area

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very good, (926)
"Great place! The staff was very nice and the property was very cute! Loved the waterfall pool "
Kahana Falls Maui by VRI Americas
Napili Shores Maui by OUTRIGGER
On the beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1663)
"The location was great to restaurants and the beach."
The price is S$407
includes taxes & fees
3 Oct - 4 Oct
Napili Shores Maui by OUTRIGGER
Aston at The Whaler on Kaanapali Beach
View from room

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1487)
"Clean with a beach view nice gym and pool "
Aston at The Whaler on Kaanapali Beach
Aston Maui Hill
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (827)
"Very nice and budget friendly."
The price is S$455
includes taxes & fees
22 Sept - 23 Sept
Aston Maui Hill
OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2837)
"Very clean and convenient, great location and great beaches"
The price is S$1,066
includes taxes & fees
19 Oct - 20 Oct
OUTRIGGER Honua Kai Resort & Spa
Maui Beach Vacation Club
Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (798)
"Just a great stay! "
Maui Beach Vacation Club
Aston Mahana at Kaanapali
Outdoor pool

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1654)
"I want to come back and stay on the ground floor oceanfront room."
Aston Mahana at Kaanapali
Aston at Papakea Resort
Surfing/boogie boarding

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1383)
"Everything was excellent "
Aston at Papakea Resort
The Westin Ka'anapali Ocean Resort Villas
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1114)
"The resort was beautiful. The hospitality in all seas was top notch. "
The price is S$677
includes taxes & fees
28 Sept - 29 Sept
The Westin Ka'anapali Ocean Resort Villas
Kapalua Villas Maui
1 bedroom, in-room safe, individually decorated, individually furnished

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 S$1,030
includes taxes & fees
19 Oct - 20 Oct
Kapalua Villas Maui
Castle Kama'ole Sands
Balcony

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very good, (2256)
" Loved the grounds, full of beautiful tropical plantings. Nice pool area and places to grill outdoors. All building have lanais with tables. Only a short walk to the beach and the Pacific ocean. Great sunsets!"
Castle Kama'ole Sands
The Westin Nanea Ocean Villas, Ka'anapali
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (468)
"Very nice place to stay"
The price is S$847
includes taxes & fees
8 Oct - 9 Oct
The Westin Nanea Ocean Villas, Ka'anapali
Kahana Beach Vacation Club
Living area

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very good, (716)
"Great place to stay "
Kahana Beach Vacation Club
Maui Sunset
Terrace/patio

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (470)
"Good place to spend your vacation "
Maui Sunset
AEI at Kaanapali Shores
Exterior

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (457)
"Clean, comfy,friendly staff, close to stores and beaches"
AEI at Kaanapali Shores
Marriott's Maui Ocean Club - Lahaina & Napili Towers
3 outdoor pools, pool cabanas (surcharge), pool loungers

Marriott's Maui Ocean Club - Lahaina & Napili Towers

4.0 star property
8.8 out of 10, Excellent, (191)
"It was a great place to spend a vacation for the whole family. "
The price is S$677
includes taxes & fees
3 Oct - 4 Oct
Marriott's Maui Ocean Club - Lahaina & Napili Towers
The Gardens at West Maui
Iron/ironing board, free WiFi

The Gardens at West Maui

3.0 star property
8.4 out of 10, Very good, (499)
"Great for family! "
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Olowalu Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"Great stay. Do not hesitate to book this hotel, we had a great time and great view. "
Anthony 3-night trip
Posted 1 day ago
Aston Kaanapali Shores

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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’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 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.