An underwater scene with a diver and a turtle.

Search Holiday Rentals in Olowalu

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Olowalu holiday rentals

1. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,318 reviews)
"We loved the grounds and people. Definitely will be booking to stay there, again."
United States
Scot
The price is £181
includes taxes & fees
24 Sept - 25 Sept
Aston Kaanapali Shores

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (971 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is £245
includes taxes & fees
19 Oct - 20 Oct
Aston Maui Hill

3. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,881 reviews)
"Love this place!"
United States
Diana
The price is £224
includes taxes & fees
22 Sept - 23 Sept
Napili Shores Maui by OUTRIGGER

4. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,046 reviews)
"Beautiful property, kind staff, Dukes restaurant was awesome & located on property!! Will definitely come back again!!"
United States
Diana
The price is £676
includes taxes & fees
20 Oct - 21 Oct
OUTRIGGER Honua Kai Resort & Spa

5. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (471 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
The price is £490
includes taxes & fees
5 Oct - 6 Oct
The Whaler Resort Kaanapali Beach

6. LAHAINA SHORES #105 OCEANFRONT SUITE, 2Bath 1Bedroom GROUND FLOOR

LAHAINA SHORES #105 OCEANFRONT SUITE, 2Bath 1Bedroom GROUND FLOOR
Lahaina
10.0 out of 10, Exceptional, (178 reviews)
"Lovely stay!"
United States
laura h.
The price is £408
includes taxes & fees
23 Sept - 24 Sept
LAHAINA SHORES #105 OCEANFRONT SUITE, 2Bath 1Bedroom GROUND FLOOR

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (230 reviews)
"Great place! It’s quite and 30 seconds to the beach."
United States
Alysson E
The price is £157
includes taxes & fees
9 Oct - 10 Oct
Napili Village Hotel

8. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is £249
includes taxes & fees
21 Sept - 22 Sept
Napili Sunset on the Beach

9. Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Wailuku
9.4 out of 10, Exceptional, (69 reviews)
"Great location to harbor for whale watching and good distance between airport and beaches. "
United States
Kellie B.
Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

10. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (101 reviews)
"Awesome"
United States
Gerald
The price is £721
includes taxes & fees
27 Sept - 28 Sept
Honua Kai Konea Resort by KBM

11. 🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (143 reviews)
"We enjoyed the resort and the condo was perfect"
United States
Shelley S.
The price is £460
includes taxes & fees
30 Sept - 1 Oct
🤙 Sept-Oct-Nov SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

12. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,633 reviews)
"Loved the waterfront cafe and beautiful beach!"
United States
Sabrina
The price is £269
includes taxes & fees
5 Oct - 6 Oct
Aston Maui Kaanapali Villas

13. Newly Remodeled Steps to Sugar Beach!

Newly Remodeled Steps to Sugar Beach!
North Kihei
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay in Maui! Freshly and tastefully updated, amazing patio and literally steps away from a beach. Stayed here with a family of 6 comfortably."
United States
Dmitriy K.
The price is £315
includes taxes & fees
18 Oct - 19 Oct
Newly Remodeled Steps to Sugar Beach!

14. The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (531 reviews)
"We were extremely satisfied with our stay. The hotel was clean, comfortable, and welcoming, and we had a wonderful experience. We truly enjoyed our time here and would definitely love to come back again. Highly recommended!"
United States
Hassenat
The price is £496
includes taxes & fees
3 Oct - 4 Oct
The Westin Nanea Ocean Villas, Ka'anapali

15. Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is £343
includes taxes & fees
30 Sept - 1 Oct
Romantic Beachfront Getaway

16. Unit 22 Waena Inn - Maui Private Suite

Unit 22 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (38 reviews)
"The studio is super cute and in a convenient location, it was very clean and the check in process was really easy!"
United States
Claire R.
The price is £218
includes taxes & fees
28 Sept - 29 Sept
Unit 22 Waena Inn - Maui Private Suite

17. 2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
South Kihei
9.8 out of 10, Exceptional, (218 reviews)
"Great stay! Cute place, clean and comfortable, wonderful hosts! Mahalo!"
United States
Sarah H.
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

18. Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (221 reviews)
"Has everything you need and you cannot beat the location. Everything works, slept great, would definitely book again"
United States
Michelle S.
The price is £343
includes taxes & fees
30 Sept - 1 Oct
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

19. ☀️Last min. booking SALE! KA-193 Breathtaking mountain & ocean view. 3 Bedroom☀️

☀️Last min. booking SALE! KA-193 Breathtaking mountain & ocean view. 3 Bedroom☀️
Kannapali Beach Area
9.8 out of 10, Exceptional, (88 reviews)
"Great condo with good amenities. Excellent location. Great views. Plenty of space for the family. Condo is quiet."
United States
Stacey A.
The price is £1,308
includes taxes & fees
24 Sept - 25 Sept
☀️Last min. booking SALE! KA-193 Breathtaking mountain & ocean view. 3 Bedroom☀️

20. Oceanfront, Million-Dollar-View, B421

Oceanfront, Million-Dollar-View, B421
Central Kihei
10.0 out of 10, Exceptional, (205 reviews)
"Fantastic week! The condo has everything we needed more."
United States
Laura O.
The price is £606
includes taxes & fees
21 Sept - 22 Sept
Oceanfront, Million-Dollar-View, B421
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Olowalu Hotel Reviews

Find out more about Olowalu

Everything you need to know about Olowalu holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Olowalu holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Olowalu holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olowalu holiday rentals we have selected for you start as low as £157 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 holiday 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 holiday.

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. 

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

Kaiholo Hale: This holiday home rental outside of 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 Whalers Village 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.